A resonance-assisted intra­molecular hydrogen bond in compounds containing 2-hy­droxy-3,5-di­nitro­benzoic acid and its various deprotonated forms: redetermination of several related structures

Fábry, J.

doi:10.1107/S2056989018011544

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ISSN: 2056-9890

Volume 74| Part 9| September 2018| Pages 1344-1357

https://doi.org/10.1107/S2056989018011544

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A resonance-assisted intramolecular hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms: redetermination of several related structures

Jan Fábry ^a ^*

^aInstitute of Physics, Czech Academy of Sciences, Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: fabry@fzu.cz

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 23 July 2018; accepted 15 August 2018; online 24 August 2018)

A large number of structural determinations of compounds containing 2-hydroxy-3,5-dinitrobenzoic acid (I) and its various deprotonated forms, 2-hydroxy-3,5-dinitrobenzoate (II) or 2-carboxy-4,6-dinitrophenolate (III), are biased. The reason for the bias follows from incorrectly applied constraints or restraints on the bridging hydrogen, which is involved in the intramolecular hydrogen bond between the neighbouring carboxylic/carboxylate and oxo/hydroxy groups. This hydrogen bond belongs to the category of resonance-assisted hydrogen bonds. The present article suggests corrections for the following structure determinations that have been published in Acta Crystallographica: DUJZAK, JEVNAA, LUDFUL, NUQVEB, QIQJAD, SAFGUD, SEDKET, TIYZIM, TUJPEV, VABZIJ, WADXOR, YAXPOE [refcodes are taken from the Cambridge Structural Database [CSD; Groom et al. (2016 ). Acta Cryst. B72, 171–179]. The structural features of the title molecules in all the retrieved structures, together with structures that contain 3,5-dinitro-2-oxidobenzoate (IV), are discussed. Attention is paid to the localization of the above-mentioned bridging hydrogen, which can be situated closer to the O atom of the carboxylate/carboxylic group or that of the hydroxy/oxo group. In some cases, it is disordered between the two O atoms. The position of the bridging hydrogen seems to be dependent on the pK_a(base) although with exceptions. A stronger basicity enhances the probability of the presence of a phenolate (III). The present article examines the problem of the refinement of such a bridging hydrogen as well as that of the hydrogen atoms involved in the hydroxy and primary and secondary amine groups. It appears that the best model, in many cases, is obtained by fixing the hydrogen-atom position found in the difference electron-density map while refining its isotropic displacement parameter.

Keywords: crystal structure; resonance-assisted hydrogen bonds; refinement constraints; 2-hydroxy-3,5-dinitrobenzoic acid; 2-hydroxy-3,5-dinitrobenzoate; 2-carboxy-4,6-dinitrophenolate; 3,5-dinitro-2-oxidobenzoate.

CCDC references: 1862187; 1862188; 1862189; 1862190; 1862191; 1862192; 1862193; 1862194; 1862195; 1862196; 1862197; 1862198

1. Chemical context

2-Hydroxy-3,5-dinitrobenzoic acid (I; alternatively 3,5-dinitrosalicylic acid, DNSA), 2-hydroxy-3,5-dinitrobenzoate (II; alternatively 3,5-dinitrosalicylate), 2-carboxy-4,6-dinitrophenolate (III) and 3,5-dinitro-2-oxidobenzoate (IV), are molecules that have interesting structural and chemical features. Such molecules have been studied because of the proton transfer from the carboxylic group, which is dependent on its environment (e.g. Smith et al., 2007 ). Thus, three deprotonated forms of molecule I have been observed. The last one, IV, is deprived of all of the hydrogen atoms while the others differ in the localization of the hydrogen atom involved in the intramolecular hydrogen bond between the O atoms of the carboxylate/carboxylic and the hydroxy/oxo groups. In the different structures, this hydrogen atom may be closer to either oxygen atom, depending on the properties of each particular structure. In some cases, this hydrogen atom may even be disordered. In the following, it will be referred to as a bridging hydrogen.

Such a bridging hydrogen is a part of a resonance-assisted moiety (Gilli & Gilli, 2009 ) composed of six atoms with the pertinent bonds being D1, D2, D3, D4, D11 and D12, as shown in Fig. 1a. However, the delocalized bonds can be further extended within the molecule, especially to the C=O/C—OH bond (D1/D5 in Fig. 1a). Resonance-assisted hydrogen bonds tend to be stronger and therefore the bridging hydrogen should be displaced towards the hydrogen-bond centre. On the other hand, O⋯H⋯O hydrogen bonds with a bridging hydrogen that is situated about its centre are usually observed for strong intramolecular hydrogen bonds with the O⋯O distances being shorter than 2.5 Å (Gilli & Gilli, 2009), while the O⋯H⋯O angles tend to be close to 180° (Jeffrey, 1995 ). The O_{carboxylate/carboxylicgroup}⋯O_{hydroxy/oxo group} distance can be as short as 2.41 Å in some 2-hydroxy-3,5-dinitrobenzoates (II) or 2-carboxy-4,6-dinitrophenolates (III); however, the O⋯H⋯O angle, which is ca 160°, situates it in a category of its own.

Figure 1
Definition of bonds and various angles in I–IV.

The above-mentioned features of the intramolecular O⋯H⋯O hydrogen bond in the molecules considered herein have been ignored on many occasions by incorrectly applied constraints or severe restraints on the O—H distances, 0.82 or 0.84 Å, together with angle constraints/restraints equal to 109° as proposed by SHELXL (Sheldrick, 2008 , 2015 ).

A robust indication whether the bridging hydrogen has been positioned correctly follows from the bond distances C=O/C—O of the involved carboxylate/carboxylic and hydroxyl/oxo groups, although there are a few exceptions in which the bridging hydrogen is attached to the oxygen forming a slightly shorter C—O distance. These exceptions will be mentioned briefly below. Thus, it seems that a considerable number of the structures containing the molecules I–IV could have been determined more correctly with a more realistic description of the pertinent hydrogen bond in these molecular fragments.

A search of the Cambridge Structural Database (CSD, Version 3.58, last update May 2017; Groom et al., 2016) indicated that 27 structures out of 53 reported as 2-hydroxy-3,5-dinitrobenzoates (II) seem to be suspect; 21 structures out of 70 reported as 2-carboxy-4,6-dinitrophenolates (III) seem to be suspect, and nine structures out of 15 that contain a molecule of 2-hydroxy-3,5-dinitrobenzoic acid (I) also appear to be suspect. Figs. 2a and 2b illustrate this situation for 2-hydroxy-3,5-dinitrobenzoates (II) and 2-carboxy-4,6-dinitrophenolates (III), respectively.

Figure 2
The dependence of bond distances: (a) D2 on D4 for structures that were originally determined as 2-hydroxy-3,5-dinitrobenzoate (II), or as containing 2-hydroxy-3,5-dinitrobenzoic acid (I); (b) D1 on D3 for the structures that were determined as 2-carboxy-4,6-dinitrophenolate (III). Colour code for symbols: black squares are the data retrieved from the CSD; red circles are the corrected title structures; green and blue triangles are the original and the corrected structure of LUDFUL, which contains a molecule of 2-hydroxy-3,5-dinitrobenzoic acid (I).

It is plausible to expect that the environment affects the position of the bridging hydrogen. Therefore, it can be assumed that the proton transfer stemming from the carboxyl group will affect its position.

The data for the suspect structures published in Acta Crystallographica were retrieved from the journal's web page and recalculated. Tables 1 and 2 contain an overview of those structures, which were successfully redetermined. In the following, these structures are referred to by their CSD refcodes; for the pertinent chemical names, see Table 2.

Table 1
Experimental details

	DUJZAK	JEVNAA	LUDFUL	NUQVEB
Crystal data
Chemical formula	[Ag(C₉H₇NO)₂](C₇H₃N₂O₇)	[Zn(C₃H₄N₂)₄](C₇H₃N₂O₇)₂	C₇H₄N₂O₇·C₁₂H₈N₂	C₆H₉N₂⁺·C₇H₃N₂O₇⁻
M_r	625.30	791.93	408.33	336.27
Crystal system, space group	Monoclinic, P2₁	Monoclinic, C2/c	Monoclinic, P2₁/a	Triclinic, P $[\overline{1}]$
Temperature (K)	293	293	293	100
a, b, c (Å)	9.0154 (18), 7.6122 (15), 17.138 (3)	25.0809 (15), 6.7251 (4), 18.9145 (10)	14.8002 (15), 7.4029 (16), 16.0091 (16)	5.8673 (7), 8.0991 (9), 15.2437 (17)
α, β, γ (°)	90, 104.38 (3), 90	90, 97.658 (6), 90	90, 96.395 (8), 90	86.844 (3), 84.252 (3), 81.209 (3)
V (Å³)	1139.3 (4)	3161.9 (3)	1743.1 (5)	711.69 (14)
Z	2	4	4	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.95	0.87	0.12	0.13
Crystal size (mm)	0.20 × 0.15 × 0.11	0.20 × 0.18 × 0.10	0.36 × 0.34 × 0.26	0.29 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector	Bruker APEXII area-detector	Enraf–Nonius CAD-4	Bruker APEX DUO CCD area-detector
Absorption correction	–	Multi-scan (SADABS; Bruker, 1999)	–	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	–	0.846, 0.918	–	0.963, 0.990
No. of measured, independent and observed [I > 3σ(I)] reflections	10841, 4602, 4225	20634, 3635, 2152	8396, 4202, 1587	12709, 4943, 3677
R_int	0.022	0.058	0.056	0.023
(sin θ/λ)_max (Å⁻¹)	0.651	0.651	0.661	0.756

Refinement
R factors and goodness of fit	R[F > 3σ(F)] = 0.023, wR(F) = 0.053, S = 1.34	R[F > 3σ(F)] = 0.036, wR(F) = 0.075, S = 1.23	R[F > 3σ(F)] = 0.044, wR(F) = 0.083, S = 1.08	R[F > 3σ(F)] = 0.042, wR(F) = 0.109, S = 2.06
No. of reflections	4602	3635	4202	4943
No. of parameters	356	244	274	222
No. of restraints	0	0	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	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)	0.44, −0.30	0.23, −0.23	0.29, −0.31	0.40, −0.32
Absolute structure	1800 of Friedel pairs used in the refinement	–	–	–
Absolute structure parameter	0.004 (17)	–	–	–

	QIQJAD	SAFGUD	SEDKET	TIYZIM
Crystal data
Chemical formula	C₉H₈Cl₂N₅⁺·C₇H₃N₂O₇⁻·C₃H₇NO	[Ag(C₁₂H₆N₂O₂)](C₇H₃N₂O₇)	C₅H₉N₂⁺·C₇H₃N₂O₇⁻	C₆H₁₂N₃⁺·C₇H₃N₂O₇⁻
M_r	557.31	755.36	324.26	353.30
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/c	Monoclinic, P2₁	Triclinic, P $[\overline{1}]$
Temperature (K)	294	174	293	173
a, b, c (Å)	10.0227 (5), 10.5507 (5), 12.5359 (6)	11.757 (2), 18.297 (4), 13.223 (3)	8.1183 (7), 6.0636 (5), 14.1453 (11)	7.0109 (4), 10.6617 (8), 10.7454 (7)
α, β, γ (°)	81.858 (1), 71.888 (1), 70.009 (1)	90, 103.91 (3), 90	90, 91.904 (1), 90	93.075 (6), 95.863 (5), 104.944 (6)
V (Å³)	1183.1 (1)	2761.1 (11)	695.93 (10)	769.30 (9)
Z	2	4	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Cu Kα
μ (mm⁻¹)	0.34	0.81	0.13	1.09
Crystal size (mm)	0.16 × 0.14 × 0.08	0.3 × 0.24 × 0.2	0.40 × 0.27 × 0.11	0.22 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector	Oxford Diffraction Gemini R Ultra	Bruker SMART CCD	Agilent Xcalibur (Eos, Gemini)
Absorption correction	Multi-scan (SADABS; Bruker, 2001)	Multi-scan (SADABS; Bruker, 2002)	Multi-scan (SADABS; Bruker, 2002)	Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)
T_min, T_max	0.93, 0.97	0.780, 0.910	0.959, 0.986	0.925, 1.000
No. of measured, independent and observed [I > 3σ(I)] reflections	13936, 5507, 4441	12726, 5013, 3100	3523, 2301, 1444	4664, 2953, 2426
R_int	0.019	0.052	0.040	0.026
(sin θ/λ)_max (Å⁻¹)	0.661	0.603	0.595	0.618

Refinement
R factors and goodness of fit	R[F > 3σ(F)] = 0.056, wR(F) = 0.147, S = 3.41	R[F > 3σ(F)] = 0.062, wR(F) = 0.118, S = 1.64	R[F > 3σ(F)] = 0.041, wR(F) = 0.088, S = 1.16	R[F > 3σ(F)] = 0.041, wR(F) = 0.100, S = 1.64
No. of reflections	5507	5013	2301	2953
No. of parameters	340	444	212	229
No. of restraints	0	0	0	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	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)	0.80, −0.36	0.76, −0.63	0.11, −0.10	0.21, −0.18
Absolute structure	–	–	955 Friedel pairs used in the refinement	–
Absolute structure parameter	–	–	0.5	–

	TUJPEV	(VABZIJ)	WADXOR	YAXPOE
Crystal data
Chemical formula	C₁₀H₁₂N₃O₃S⁺·C₇H₃N₂O₇⁻	C₈H₁₃N₂O⁺·C₇H₃N₂O₇⁻·H₂O	C₉H₁₇N₂⁺·C₇H₃N₂O₇⁻	C₂₆H₂₉N₂⁺·C₇H₃N₂O₇⁻
M_r	481.41	398.33	380.35	596.63
Crystal system, space group	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n	Monoclinic, P2₁/c
Temperature (K)	296	100	200	200
a, b, c (Å)	8.5551 (1), 10.5000 (2), 12.7576 (3)	6.6691 (3), 11.3831 (4), 12.2900 (5)	6.1537 (3), 19.1541 (14), 14.5527 (11)	14.5648 (3), 12.9374 (3), 16.1619 (3)
α, β, γ (°)	106.463 (1), 100.913 (1), 108.272 (1)	89.727 (2), 76.771 (2), 76.930 (2)	90, 98.343 (6), 90	90, 103.900 (1), 90
V (Å³)	993.72 (3)	883.62 (6)	1697.2 (2)	2956.22 (11)
Z	2	2	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.23	0.13	0.12	0.10
Crystal size (mm)	0.20 × 0.20 × 0.16	0.52 × 0.13 × 0.10	0.30 × 0.13 × 0.10	0.51 × 0.26 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII CCD	Bruker SMART APEXII CCD area-detector	Oxford Diffraction Gemini-S CCD-detector	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)	Multi-scan (SADABS; Bruker, 2009)	Multi-scan (CrysAlis PRO; Agilent, 2014)	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.955, 0.964	0.937, 0.987	0.920, 0.990	0.932, 1.000
No. of measured, independent and observed [I > 3σ(I)] reflections	24261, 6717, 4398	17014, 4061, 3042	7800, 3339, 1976	29552, 7344, 5724
R_int	0.030	0.030	0.034	0.015
(sin θ/λ)_max (Å⁻¹)	0.758	0.650	0.617	0.667

Refinement
R factors and goodness of fit	R[F > 3σ(F)] = 0.044, wR(F) = 0.104, S = 1.95	R[F > 3σ(F)] = 0.038, wR(F) = 0.086, S = 1.77	R[F² > 2σ(F²)] = 0.046, wR(F²) = 0.095, S = 1.33	R[F > 3σ(F)] = 0.054, wR(F) = 0.190, S = 1.80
No. of reflections	6717	4061	3339	7344
No. of parameters	301	258	268	399
No. of restraints	0	0	2	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	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)	0.31, −0.35	0.46, −0.23	0.36, −0.24	0.63, −0.28
Absolute structure	–	–	–	–
Absolute structure parameter	–	–	–	–

Table 2
Overview of the redetermined structures

REFCODE	Chemical name original/corrected if necessary
DUJZAK^a	Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate
JEVNAA^b	Tetrakis(1H-imidazole-N³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate / tetrakis(1H-imidazole-N³)zinc(II) bis(2-carboxy-4,6-dinitrophenolate)
LUDFUL^c	1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / phenazine 2-hydroxy-3,5-dinitrobenzoic acid
NUQVEB^d	2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) / 2-amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) (0.38) / 2-amino-5-methylpyridinium 2-carboxy-4,6-dinitrophenolate (0.62)
QIQJAD^e	3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide solvate / 3,5-dinitro-2-hydroxybenzoate (0.55) 2-carboxy-4,6-dinitrophenolate (0.45) N,N-dimethylformamide monosolvate / 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate
SAFGUD^f	Bis(1,10-phenanthroline-5,6-dione-2N,N′)silver(I) 2-hydroxy-3,5-dinitrobenzoate / bis(1,10-phenanthroline-5,6-dione-2N,N′)silver(I) 2-carboxy-4,6-dinitrophenolate
SEDKET^g	3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate / 3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate
TIYZIM^h	3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate
TUJPEVⁱ	4-[(5-methylisoxazol-3-yl)aminosulfonyl]anilinium 3,5-dinitrosalicylate
VABZIJ^j	2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolatemonohydrate
WADXOR^k	1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-hydroxy-3,5-dinitrobenzoate (0.73) / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-carboxy-4,6–2-carboxy-4,6-dinitrophenolate (0.37)
YAXPOE^l	4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate
Notes: (a) Zhang & Jian (2009); (b) Huang et al. (2007); (c) Senthil Kumar et al. (2002); (d) Hemamalini & Fun (2010a); (e) Sridhar et al. (2013); (f) Wang et al. (2012); (g) Wei et al. (2012); (h) Yamuna et al. (2014); (i) Malathy et al. (2015); (j) Hemamalini & Fun (2010b); (k) Smith & Lynch (2016); (l) Dayananda et al. (2012).

Notably, JEVNAA turns out not to be a substituted benzoate but a phenolate. NUQVEB though reported as a substituted benzoate turns out to be present in a disordered benzoate and a phenolate form. QIQJAD though reported as a disordered benzoate and a phenolate turns out to be a substituted benzoate. SAFGUD was reported as a substituted benzoate but turns out to be a phenolate. WADXOR was reported as a substituted benzoate that is disordered over two positions but it turns out to be present both in a dominant benzoate as well as in a minor phenolate form. Finally, SEDKET was originally determined as a substituted phenolate but it turns out to be a benzoate.

Some of the retrieved structures were difficult or impossible to recalculate with sufficient accuracy: HILPOI (trimethoprimium 3,5-dinitrosalicylate; Subashini et al., 2007 ) because of an abnormally low proportion of observed reflections (moreover the bridging hydrogen H6a is situated out of the plane between the carboxylate and hydroxy oxygen atoms, which seems to indicate an error) and VUZNEK (3,4-diaminopyridinium 2-carboxy-4,6-dinitrophenolate; Hemamalini & Fun, 2010b ) because of the disorder present in the structure.

2. Refinement of the title structures

For each structure, two methods have been applied for the refinement of the hydrogen atoms involved in hydrogen bonding. In Method 1, the positions of the bridging hydrogens as well as those of the hydroxy, primary and secondary amine and ammonium hydrogen atoms were fixed after their localization in the difference electron-density maps while their displacement parameters were refined. In Method 2, the positional parameters of the latter hydrogen atoms were refined while their displacement parameters were constrained in the usual manner: U_iso(H) = 1.2U_eq(N_amine) or U_iso(H) = 1.5U_eq(O_hydroxy) or U_iso(H) = 1.5U_eq(N_ammonium).

The appropriate sections of the difference electron-density maps of the title structures (see supplementary Fig. S1) show regions with the hydroxy, amine and ammonium hydrogen atoms. These sections comprise the maps that were obtained after the refinement of the models without the pertinent hydrogen atoms as well as the maps that were calculated by either refinement method. It can be seen from the supplementary Fig. S1 that one of the reasons that hinders the correct localization of the hydrogen atoms involved in the hydrogen bonds is an apparent non-spherical electron density of the donor and acceptor atoms. Thus, hydrogen-atom localization by X-ray diffraction is hindered not only by its weak scattering power, but also by the polarization of its electron density resulting from the proximity of the acceptor and by the asphericity of the electron density of the donor and acceptor atoms. Therefore, refinement Method 1 was given preference. The hydrogen bonds in the title structures are listed in Table 3, which shows that there might be quite a large difference between the results with the fixed and the refined positional parameters of such hydrogen atoms. In the following, a detailed description of the refinement of the recalculated structures is given:

Table 3
Hydrogen bonds (Å, °) in the redetermined structures

The upper entries for each hydrogen bond refer to refinement Method 1: fixed hydrogen-atom positions, which were obtained from the difference electron-density maps, and refined displacement parameters. The lower entries refer to refinement Method 2: refined hydrogen-atom positions and constrained displacement parameters.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
DUJZAK
O1—H1aa⋯O8	0.759 (2)	1.859 (2)	2.606 (3)	167.96 (14)
	0.97 (4)	1.64 (4)	2.603 (3)	175 (3)
O2—H2aa⋯O9	0.922 (2)	1.727 (2)	2.631 (3)	166.48 (15)
	0.75 (4)	1.90 (4)	2.636 (3)	165 (4)
O3—H3b⋯O9	1.040 (2)	1.495 (2)	2.481 (3)	155.88 (12)
	1.11 (4)	1.41 (4)	2.480 (3)	160 (3)

JEVNAA
O2—H1a⋯O1	1.039 (2)	1.496 (2)	2.498 (2)	160.4 (1)
	0.89 (2)	1.65 (3)	2.503 (2)	160 (2)
N2—H2a⋯O3	0.967 (2)	1.890 (2)	2.838 (3)	165.9 (1)
	0.84 (2)	2.02 (2)	2.845 (3)	169 (2)
N4—H4a⋯O1ⁱ	0.943 (2)	1.924 (1)	2.784 (2)	150.6 (1)
	0.86 (2)	1.95 (2)	2.792 (2)	165 (2)

LUDFUL
O3—H3a⋯O2	1.059 (1)	1.530 (1)	2.513 (2)	151.7 (1)
	1.06 (2)	1.51 (2)	2.516 (2)	156 (2)
O1—H1a⋯N3	1.163 (1)	1.416 (1)	2.552 (2)	163.2 (1)
	1.14 (2)	1.44 (2)	2.552 (2)	166 (2)

NUQVEB
O7—H1o7⋯O1	0.919 (1)	1.531 (1)	2.4202 (12)	161.55 (6)
	1.14 (2)	1.31 (2)	2.4178 (12)	163 (2)
O1—H1o1⋯O7	0.931 (1)	1.513 (1)	2.4202 (12)	163.52 (6)
	1.31 (2)	1.14 (2)	2.4178 (12)	163 (2)
N2—H2a⋯O7ⁱⁱ	0.892 (1)	2.079 (1)	2.9655 (14)	172.84 (6)
	0.87 (1)	2.095 (14)	2.9674 (14)	176.5 (12)
N2—H2b⋯O1ⁱⁱⁱ	0.846 (1)	2.165 (1)	2.8526 (14)	138.40 (6)
	0.88 (2)	2.146 (14)	2.852 (1)	137.3 (11)
N2—H2b⋯O2ⁱⁱⁱ	0.846 (1)	2.413 (1)	3.1741 (14)	150.02 (6)
	0.88 (2)	2.384 (14)	3.1736 (15)	150.3 (11)
N1—H1⋯O6ⁱⁱ	0.898 (1)	1.783 (1)	2.6781 (13)	174.83 (6)
	0.90 (1)	1.784 (14)	2.6773 (14)	173.3 (13)

QIQJAD
N3—H3n⋯O2	0.862 (2)	1.994 (2)	2.854 (2)	174.8 (1)
	0.81 (3)	2.05 (3)	2.854 (3)	175 (3)
N3—H4n⋯O8^iv	0.863 (2)	2.059 (1)	2.921 (2)	176.9 (1)
	0.85 (2)	2.07 (2)	2.920 (2)	173 (3)
N2—H2n⋯O1	0.897 (2)	1.831 (2)	2.728 (2)	177.5 (1)
	0.81 (3)	1.93 (3)	2.731 (2)	171 (2)
N5—H5n⋯N4^v	0.866 (1)	2.141 (1)	2.9992 (19)	171.1 (1)
	0.84 (2)	2.17 (2)	2.999 (2)	171 (2)
N5—H6n⋯O8^vi	0.863 (2)	2.041 (2)	2.760 (2)	140.2 (1)
	0.78 (2)	2.12 (3)	2.764 (2)	141 (2)
O3—H3o⋯O1	0.926 (1)	1.562 (1)	2.4572 (18)	161.3 (1)
	0.99 (3)	1.49 (3)	2.4569 (19)	164 (3)

SAFGUD
O8—H7⋯O7	1.155 (4)	1.346 (4)	2.462 (6)	159.6 (3)
	1.05 (7)	1.57 (7)	2.452 (7)	138 (6)

SEDKET
O1—H2a⋯O2	1.22 (5)	1.34 (5)	2.476 (3)	149 (5)
	1.27 (3)	1.29 (3)	2.477 (3)	151 (3)
O2—H2a⋯O1	1.34 (5)	1.22 (5)	2.476 (3)	149 (5)
	1.29 (3)	1.27 (3)	2.477 (3)	151 (3)
N1—H1⋯O1^vii	1.11 (5)	1.92 (5)	2.799 (4)	133 (3)
	0.99 (4)	2.00 (3)	2.804 (4)	137 (3)
N1—H1⋯O7^vii	1.11 (5)	1.94 (5)	2.850 (4)	137 (3)
	0.99 (4)	2.03 (3)	2.855 (4)	140 (3)
N2—H2⋯O3	0.96 (3)	1.77 (3)	2.685 (4)	158 (3)
	0.99 (3)	1.75 (3)	2.684 (4)	157 (3)

TIYZIM
O2b—H2b⋯O1b	0.982 (1)	1.516 (1)	2.4473 (16)	156.3 (1)
	1.02 (2)	1.48 (2)	2.4476 (16)	156 (2)
N3a—H3aa⋯N1aa^viii	0.904 (1)	1.932 (1)	2.797 (2)	159.6 (1)
	0.91	1.92	2.797 (2)	162
N3a—H3ab⋯O2b^ix	0.901 (1)	2.565 (1)	3.1297 (17)	121.4 (1)
	0.91	2.58	3.1298 (17)	120
N3a—H3ab⋯O2b^ix	0.901 (1)	2.565 (1)	3.1297 (17)	121.4 (1)
	0.91	2.58	3.1297 (18)	120
N3a—H3ab⋯O3b^ix	0.901 (1)	2.072 (1)	2.9537 (17)	165.8 (1)
	0.91	2.06	2.9542 (17)	165
N3a—H3ac⋯O1b^x	0.893 (1)	2.061 (1)	2.815 (2)	141.5 (1)
	0.91	2.03	2.815 (2)	144
N3a—H3ac⋯O7b^x	0.893 (1)	2.484 (1)	2.9712 (19)	114.7 (1)
	0.91	2.46	2.9706 (19)	116

TUJPEV
O6—H6a⋯O5	1.184 (1)	1.295 (1)	2.4268 (16)	156.58 (6)
	1.24 (2)	1.21 (2)	2.4280 (17)	165.3 (14)
N1—H1a⋯O6^xi	1.002 (1)	2.068 (1)	3.0655 (17)	173.55 (7)
	0.89	2.24	3.0694 (17)	155
N1—H1b⋯N3^v	0.793 (1)	2.292 (1)	3.0393 (15)	157.3 (1)
	0.89	2.20	3.0382 (15)	157
N1—H1c⋯O4^v	0.832 (2)	1.831 (1)	2.663 (2)	177.1 (1)
	0.89	1.77	2.660 (2)	175
N2—H2a⋯O5	0.970 (1)	1.844 (1)	2.7852 (15)	162.64 (9)
	0.827 (17)	1.986 (16)	2.7900 (16)	164.0 (18)

VABZIJ
N3—H1n3⋯O6^x	0.973 (1)	1.754 (1)	2.7182 (14)	170.48 (8)
	0.91 (1)	1.823 (14)	2.7214 (14)	170.8 (15)
N4—H1n4⋯O1w	0.909 (1)	1.840 (1)	2.7348 (15)	167.76 (8)
	0.91 (2)	1.833 (15)	2.7323 (16)	172.0 (15)
O1w—H2w1⋯O1^xii	0.917 (1)	1.890 (1)	2.7886 (14)	166.21 (6)
	0.82 (2)	1.995 (19)	2.7906 (15)	162.7 (16)
O1w—H1w1—O3ⁱⁱⁱ	0.915 (1)	2.040 (1)	2.9352 (14)	165.84 (7)
	0.89 (2)	2.064 (18)	2.9357 (15)	168.0 (17)
O7—H7⋯O1	1.019 (1)	1.433 (1)	2.4340 (13)	165.94 (7)
	0.96 (2)	1.505 (16)	2.4358 (13)	162.0 (16)

WADXOR
N8a—H8a⋯O11b	0.960 (2)	1.933 (2)	2.864 (2)	162.83 (11)
	0.91 (2)	1.96 (2)	2.869 (2)	174.1 (17)
O11b—H21b⋯O21b	1.145 (2)	1.303 (6)	2.433 (6)	167.3 (3)
	1.07 (9)	1.48 (9)	2.430 (6)	145 (7)
O2b—H2b⋯O12b	1.103 (2)	1.385 (2)	2.471 (2)	166.81 (13)
	0.91 (3)	1.61 (3)	2.475 (3)	159 (3)

YAXPOE
N1—H71⋯O1^iv	0.945 (1)	1.954 (1)	2.813 (2)	150.01 (8)
	0.90 (2)	1.98 (2)	2.812 (2)	154.0 (19)
N1—H71⋯O2^iv	0.945 (1)	2.302 (2)	3.032 (2)	133.62 (8)
	0.90 (2)	2.36 (2)	3.034 (2)	131.8 (17)
O7—H7⋯O1	0.924 (2)	1.668 (1)	2.505 (2)	148.96 (9)
	0.92 (3)	1.71 (3)	2.504 (2)	142 (2)
Symmetry codes: (i) −x + $[{3\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1; (ii) −x + 1, −y + 1, −z; (iii) −x + 1, −y, −z; (iv) −x + 1, −y + 1, −z + 1; (v) −x + 1, −y + 2, −z + 1; (vi) x − 1, y + 1, z; (vii) −x + 1, y + $[{1\over 2}]$ , −z + 1; (viii) −x, −y, −z; (ix) x + 1, y, z; (x) −x, −y + 1, −z + 1; (xi) −x, −y + 2, −z + 1; (xii) x, y + 1, z.

DUJZAK (Zhang & Jian, 2009 ): C—H_aryl were constrained to be equal to 0.93 Å while U_iso(H_aryl) = 1.2U_eq(C_aryl). The position of the bridging hydrogen H3b as well as those of the hydroxy hydrogen atoms H1aa and H2aa were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined.

JEVNAA (Huang et al., 2007 ): C—H_aryl were constrained to be equal to 0.93 Å while U_iso(H_aryl) = 1.2U_eq(C_aryl). The position of the bridging hydrogen H1a as well as those of the secondary amine hydrogen atoms H2a and H4a were located in the difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined.

LUDFUL (Senthil Kumar et al., 2002 ): C—H_aryl were constrained to be equal to 0.93 Å while U_iso(H_aryl) = 1.2U_eq(C_aryl). The position of the bridging hydrogen H3a as well as that of the hydroxy hydrogen atom H1a were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined.

NUQVEB (Hemamalini & Fun, 2010a ): The subroutine TwinRotMax of PLATON (Spek, 2009 ) indicated non-merohedral twinning: h2 = −h1; k2 = −k1; l2 = −0.488 h1 − 0.153k1 + l1. The refinement was carried out on the non-overlapped reflections only. The refined value of the second domain fraction converged to the value −0.0006 (4). Therefore the value of the second domain fraction was set to 0 and was not refined further. C—H_aryl and C—H_methyl were constrained to be equal to 0.95 and 0.98 Å, respectively. U_iso(H_aryl) = 1.2U_eq(C_aryl) and U_iso(H_methyl) = 1.5U_eq(C_methyl). The positions of the disordered bridging hydrogens H1o1 and H1o7 as well as those of the primary (H2a, H2b) and the secondary amine hydrogen atoms (H1a) were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined; in the case of the bridging hydrogens H1o1 and H1o7, their isotropic displacement parameters were refined to be equal while their occupational parameters were refined under the condition that their sum was equal to 1.

QIQJAD (Sridhar et al., 2013 ): The subroutine TwinRotMax of PLATON (Spek, 2009) indicated non-merohedral twinning: h2 = −1.018h1 + 0.054k1; k2 = −0.673h1 + 1.018k1; l2 = −0.039h1 + 0.116k1 − l1. The refined value of the second domain fraction converged to the value 0.028 (13). Therefore the value of the second domain fraction was set to 0 and was not refined further. C—Hsp² and C—H_methyl were constrained to equal to 0.93 and 0.96 Å, respectively. U_iso(Hsp²) = 1.2U_eq(Csp²) and U_iso(H_methyl) = 1.5U_eq(C_methyl). The positions of the bridging hydrogen H3o and those of the primary (H3n, H4n, H5n, H6n) as well as of the secondary (H2n) amine hydrogen atoms were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined.

SAFGUD (Wang et al., 2012 ): C—H_aryl were constrained to be equal to 0.93 Å while U_iso(H_aryl) = 1.2U_eq(C_aryl). The bridging hydrogen H7 was located in a difference electron-density map and its position was fixed while its isotropic displacement parameter U_iso(H7) was refined.

SEDKET (Wei et al., 2012 ): The non-centrosymmetric structure is composed of the light atoms only (the heaviest atom is O) and the data collection was carried out with Mo Kα radiation. The article by Wei et al. (2012) does not indicate whether the Friedel pairs were merged and nor does it contain the value of the Flack parameter. The Flack parameter was set to 0.5 without being refined in the present model. C—H_aryl and C—H_methyl were constrained to be equal to 0.93 and 0.96 Å, respectively. U_iso(H_aryl) = 1.2U_eq(C_aryl) and U_iso(H_methyl) = 1.5U_eq(C_methyl). The position of the bridging hydrogen H2a as well as those of the secondary amine hydrogen atoms H1 and H2 were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined.

TIYZIM (Yamuna et al. (2014 ): C—H_aryl and C—H_methylene were constrained to be equal to 0.95 and 0.99 Å, respectively. U_iso(H_aryl) = 1.2U_eq(C_aryl) and U_iso(H_methylene) = 1.5U_eq(C_methylene). The position of the bridging hydrogen H2b as well as those of the ammonium hydrogen atoms (H3aa, H3ab, H3ac) were found in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined; in the case of the ammonium hydrogen atoms (H3ab, H3ac,), their displacement parameters were constrained to be equal to that of H3aa.

TUJPEV (Malathy et al., 2015 ): C—H_aryl were constrained to be equal to 0.93 Å while U_iso(H_aryl) = 1.2U_eq(C_aryl). C—H_methyl were constrained to be equal to 0.96 Å while U_iso(H_methyl) = 1.5U_eq(C_methyl). The position of the bridging hydrogen H6a as well as those of the secondary amine group H2a and of the ammonium hydrogen atoms H1a, H1b and H1c were found in a difference-electron map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined; in the case of the ammonium hydrogen atoms (H1b, H1c), their displacement parameters were constrained to be equal to that of H1a.

VABZIJ (Hemamalini & Fun, 2010c ): C—H_aryl, C—H_methyl, C—H_methine were constrained to be equal to 0.93, 0.96 and 0.98 Å, respectively. U_iso(H_aryl) = 1.2U_eq(C_aryl), U_iso(H_methine) = 1.2U_eq(C_methine), U_iso(H_methyl) = 1.5U_eq(C_methyl). The position of the bridging hydrogen H7 as well as those of the secondary amine hydrogen atom H1n4 and of the water hydrogen atoms H1w1 and H1w2 were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their displacement parameters were refined.

WADXOR (Smith & Lynch, 2016 ): The non-centrosymmetric structure is composed of light atoms only (the heaviest atoms present in the structure are oxygens) and the data collection was carried out with Mo Kα radiation. The original article reported the refined Flack parameter to be equal to −0.1 (13); however, the refinement using JANA2006 (Petříček et al., 2014 ) did not converge and therefore the Flack parameter was set to 0.5 without being refined. C—H_aryl and C—H_methylene were constrained to be equal to 0.95 and 0.99 Å, respectively, except for the distances between the methylene atom C11 and the attached hydrogen atoms H12a and H13a, which were restrained to 0.99 (1) Å (Müller, 2009 ). [The reason for the different treatment of the latter methylene group was its vicinity to the disordered methylene groups centered on C10 and C12a.] U_iso(H_aryl) = 1.2U_eq(C_aryl) and U_iso(H_methylene) = 1.2U_eq(C_methylene). There were two types of occupational disorder present in the structure. The first one was related to the fragments with the methylene carbon atoms C9a, C10a and the attached respective pairs of hydrogen atoms H91a, H92a and H10a, H11a, as well as to C13a and C12a with the attached respective pairs of hydrogen atoms H16a, H17a and H14a, H15a. The occupation parameter of C13 was refined while those of the related atoms were either set equal to that of C13 (i.e. C12a and attached hydrogen atoms) or its complement to 1 (C9a and C10a and attached hydrogen atoms). The displacement parameters of the disordered pairs of atoms C9a and C13a as well as C10a and C12a were set to be equal, i.e. that of C13a equalled that of C9a while that of C10a equalled that of C12a. The second type of occupational disorder referred to the fragments C2b—H61b, C2b–O2b—H2b and C6b—H6b, C6b—O21b—H21b. This means that the occupation parameters of H61b, H21b were set equal to the refined occupational parameter of O21b while being complements to 1 for H6b, O2b, H2b. The positions of the bridging hydrogens H2b and H21b as well as that of the primary amine hydrogen atom H8a were located in a difference electron-density map. Their positional parameters were fixed during the refinement while their isotropic displacement parameters were refined; in the case of bridging hydrogens H2b and H21b, their isotropic displacement parameters were constrained to be equal.

YAXPOE (Dayananda et al., 2012 ): C—H_aryl and C—H_methylene were constrained to equal to 0.95 and 0.99 Å, respectively. U_iso(H_aryl) = 1.2U_eq(C_aryl) and U_iso(H_methylene) = 1.5U_eq(C_methylene). The bridging hydrogen H7 was located in a difference electron-density map. Its positional parameters were fixed while U_iso(H7a) was refined. A high instability factor Δ in the weighting scheme (0.0064) was applied in order to avoid a large number of reflections with (I_obs − I_calc)/σ(w) > 10 where σ(w) = [σ²(I) + ΔI²]^−1/2. [This condition generates A alerts for Δ = 0.0004, which has been used in other refinements of the title structure, when running checkCIF (Spek, 2009).] The residual electron-density map contains peaks which are difficult to interpret (see supplementary Fig. S1).

3. Discussion of the interdependence of bond lengths and angles

For this discussion, the definition of the various bonds and angles in the moieties of I–IV (shown in the scheme), are illustrated in Figs. 1a and 1b, respectively. As already pointed out, the dependence D2 on D4 and D1 on D3 (Fig. 2) has shown that a large number of structures are biased by incorrectly applied constraints or restraints on the bridging hydrogen. However, a dubious or incorrect localization of the bridging hydrogen or the acid hydrogen is believed to affect the positions of the non-hydrogen atoms only minutely, and therefore even the biased structures can be considered further. The parameters q1 = D2 − D1 and q2 = D12 − D11 express the electron delocalization within the fragment D1–D12–D11–D2. The introduction of the parameters q1 and q2 follows an analogous discussion of resonance-assisted hydrogen bonds in the enol forms of β-diketone fragments (Gilli et al., 1989 , 2009 ). Fig. 3a shows that the distance where the structures with 2-carboxy-4,6-dinitrophenolates (III; red circles) transform into 2-hydroxy-3,5-dinitrobenzoates (II; black squares) corresponds to the shortest distance D13_min ≃ 2.41 Å, which in turn corresponds to (q1 + q2) ≃ 0.08 Å. This implies that this is the region where the bridging hydrogen has the greatest tendency to be situated about the centre of the O⋯O intramolecular hydrogen bond or disordered about it. A very similar dependence is shown in Fig. 3b, where only distances D1 and D3 are compared. The observed dependence means that the elongation of one C—O bond takes place mostly at the cost of the shortening of the neighbouring C=O bond; in other words, the distance between these two O atoms, D13 ≃ [(D13_min)² + (D2 − D1)²]^1/2 (Fig. 1). Table 4 lists the structures in which the title molecules are present in different forms. In the recalculated structure of SEDKET (Table 2) and e.g. the reported structures of KEZJIJ (Song et al., 2007 ) and KEZJIJ01 (Smith et al., 2007) that refer to the structure determination of 2-(pyridin-2-yl)pyridinium 2-carboxy-4,6-dinitrophenolate, the bridging hydrogen is attached to the O atom having the shorter C—O bond distance.

Table 4
Overview of selected structures with different forms of the molecules: 2-hydroxy-3,5-dinitrobenzoic acid (I); 2-hydroxy-3,5-dinitrobenzoate (II); 2-carboxy-4,6-dinitrophenolate (III); 3,5-dinitro-2-oxidobenzoate (IV)

The structures are ordered by ascending pK_a value of the base. The corresponding values of (q1 + q2), D13, D1, D2 and D5 (cf. Fig. 1) are also given.

	Refcode	Base and its form present in the structure	pK_a	ΔpK_a	Type	(q1 + q2) (Å)	D13 (Å)	D1 (Å)	D2 (Å)	D5 (Å)	Remarks
1	GORXAM^a	1,4-dioxane	−3.9	−6.08	I	0.204 0.196	2.547 2.545	1.219 1.220	1.337 1.336	1.307 1.300	Two independent molecules
2	GORXEQ^a	1,4-dioxane	−3.9	−6.08	I	0.235	2.601	1.206	1.343	1.319
3	GORXEQ01^a	1,4-dioxane	−3.9	−6.08	I	0.197	2.531	1.222	1.346	1.302
4	AJEBOG^b	4-cyanopyridinium	1.92	−0.26	III	0.003	2.523	1.324	1.28	1.213
5	ABULAM^c	2-aminoanilinium	<2	<-0.18	III	0.011	2.447	1.309	1.282	1.219
6	PIDCAI^c	2-aminoanilinium	<2	<-0.18	III	0.009	2.44	1.314	1.285	1.229	Wrongly attached hydrogen due to C=O distances. Originally determined as type II but it should be III.
7	PERBAR^d	3-carbamoylpyridinium	3.35	1.2	II	0.17	2.452	1.287	1.329	1.239	Wrongly attached hydrogen due to C=O distances. Originally determined as type II but it is probably III. Disorder present in the structure.
8	GIFMUE^e	1-naphthylammonium	3.92	1.74	III	0.011	2.488	1.31	1.279	1.224
9	MIPROS^f	8-aminoquinolinium	3.95	1.77	II	0.072	2.408	1.278	1.300	1.237	The bridging hydrogen is situated about the centre.
10	ABUKUF^g	4-chloroanilinium	3.98	1.80	II	0.094	2.435	1.276	1.297	1.242
11	YIVHIW^h	4-iodoanilinium	4.18	1.63	II	0.129	2.461	1.285	1.321	1.228
12	GIFNUFⁱ	1,10-phenanthrolinium	4.27	2.09	II	0.096	2.428	1.280	1.297	1.232	Determined as the type III but it is probably II (Fig. 1). The chemical name was correct.
13	FOXHAD^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	II	0.047	2.42	1.307	1.292	1.228	100 K; the reported hydrogen H3 is situated out of the plane formed by C⋯O bonds and is superficial.
14	KEZJIJ^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	III	0.07	2.422	1.293	1.296	1.231	C=O distances are about equal. The recalculation has shown that the bridging hydrogen is about the centre of the hydrogen bond, slightly closer to atom O2, which forms a shorter C=O bond.
15	KEZJIJ01^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	III	0.066	2.423	1.295	1.299	1.221	C=O distances are about equal, the hydrogen is attached to the O atom forming a shorter C=O bond.
16	FICXIZ^k	cytosinium	4.60	2.42	II	0.098	2.423	1.285	1.310	1.234	The type according to the C=O distances should be II; the bridging hydrogen was wrongly attached.
17	ABUJUE^l	anilinium	4.60	2.42	II	0.129	2.448	1.280	1.323	1.231
18	ABUKOZ^m	4-fluoroanilinium	4.65	2.47	II	0.142	2.465	1.273	1.325	1.252
19	GIFMOYⁿ	quinolinium	4.85	2.67	III	0.05	2.414	1.294	1.285	1.235	The title molecule has similarly long C=O distances.
20	ZAJHAT^o	2-amminobenzoic acid	4.96	2.78	II	0.135	2.461	1.282	1.324	1.227
21	AJEBIA^p	pyridinium	5.23	3.05	I and II	0.142 0.163	2.458 2.582	1.250	1.308	1.257	Two independent molecules
22	EGABOF^q	2-methylquinolinium	5.71	3.53	II	0.285	2.411	1.207	1.359	1.244	Outlier
23	AJECEX01^r	2,6-diaminopyridin-1-ium	6.13	3.95	II	0.072 0.121	2.435 2.464	1.298 1.295	1.309 1.332	1.241 1.237	One of the title molecules has similarly long C=O distances.
24	AJECIB^s	2-aminopyrimidinium	6.82	4.64	II	0.114 0.145	2.466 2.473	1.277 1.270	1.308 1.323	1.241 1.238
25	TUMWAB^t	1H-imidazol-3-ium	6.95	4.77	III	−0.01	2.457	1.320	1.279	1.214
26	LUMJOU^u	hydrazinium	8.12	5.94	III	0.014	2.459	1.318	1.275	1.211
27	SEDKET^v	3,5-dimethylpyrazolium	9	6.82	III	0.037	2.481	1.300	1.282	1.224
28	SEDKET^v (corrected)	3,5-dimethylpyrazolium	9	6.82	II	0.027	2.476	1.305	1.277	1.229	The bridging hydrogen after recalculation is closer to oxygen O1, which forms the shorter C=O bond (C12—O1).
29	LUDDET^w	benzylammonium	9.33	7.15	III	0.002	2.483	1.305	1.269	1.218
30	LUDDET01^w	benzylammonium	9.33	7.15	III			1.311 1.311	1.275 1.279	1.217 1.219
31	INELUI^x	1-phenylethylammonium	9.79	7.61	III	0.009 0.009	2.467 2.482	1.309 1.320	1.272 1.277	1.221 1.214
32	MILLOI^y	dicyclohexylammonium	10.4	8.22	III	0.028	2.464	1.289	1.273	1.225	The C=O distances of the title molecule are similar.
33	ACIFAT^z	4-sulfamoylanilinium	10.6	8.42	III	0.028	2.462	1.315	1.287	1.209
34	EGUTIJ^aa	methylammonium	10.6	8.42	III	0.011	2.481	1.314	1.276	1.218
35	EGUTOP^bb	triethylammonium	10.78	8.6	II	0.082	2.429	1.275	1.286	1.248
36	EGUTOP01^bb	triethylammonium	10.78	8.6	II	0.072	2.419	1.275	1.288	1.242
37	FOGZIL^cc	diethylammonium	11.09	8.91	III	0.004	2.489	1.308	1.270	1.217
38	XEBFAM^dd	piperidinium C₅H₁₁N	11.28	9.1	II and IV	0.078 0.061	2.586 2.736	1.219 1.234	1.278 1.253	1.255 1.271	One molecule of DNSA (I) is fully ionized, the other is in form II.
39	YEJZAO^ee	guanidinium	12.5	10.32	II	0.079	2.415	1.291	1.305	1.235
40	YEJZAO01^ee	guanidinium	12.5	10.32	II	0.073	2.415	1.292	1.300	1.239
References for the pK_a values: (a) https://chemaxon.com/products/calculators-and-predictors#pka; (b) https://www.chemicalbook.com/ProductMSDSDetailCB0688145_EN.htm; (c) Dean (1987 ); (d) https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide#section=pK_a; (e) https://labs.chem.ucsb.edu/zhang/liming/pdf/pKas_of_Organic_Acids_and_Bases.pdf; (f) https://binarystore.wiley.com/store/10.1002/jcc.23068/asset/supinfo/JCC_23068_sm_SuppInfo.pdf?v=1&s=e864a51d58b4cdc175f6b69c92ceddb546201e3b; (g) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (h) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (i) https://chemicalland21.com/specialtychem/finechem/1,10-PHENANTHROLINE.htm; (j) https://www.chemicalbook.com/ProductMSDSDetailCB5195697_EN.htm; (k) https://www.drugfuture.com/chemdata/cytosine.html; (l) https://pubchem.ncbi.nlm.nih.gov/compound/aniline#section=pKa; (m) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (n) Hosmane & Liebman (2009 ); (o) https://www.csun.edu/\~hcchm003/321/Ka.pdf; (p) https://pubchem.ncbi.nlm.nih.gov/compound/pyridine#section=Dissociation-Constants; (q) https://onlinelibrary.wiley.com/doi/pdf/10.1002/jcc.23068; (r) https://www.chemicalbook.com/ProductMSDSDetailCB0236195_EN.htm; (s) https://pubchem.ncbi.nlm.nih.gov/compound/2-aminopyridine#section=Dissociation-Constants; (t) https://pubchem.ncbi.nlm.nih.gov/compound/imidazole#section=pKa; (u) https://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf; (v) https://www.chemicalbook.com/ProductMSDSDetailCB2707394_EN.htm; (w) https://pubchem.ncbi.nlm.nih.gov/compound/benzylamine#section=pK_a; (x) https://www.drugbank.ca/drugs/DB04325; (z) https://pubchem.ncbi.nlm.nih.gov/compound/dicyclohexylamine#section=Dissociation-Constants; (z) https://pubchem.ncbi.nlm.nih.gov/compound/sulfanilamide#section=Dissociation-Constants; (aa) https://pubchem.ncbi.nlm.nih.gov/compound/methylamine#section=pK_a; (ab) https://pubchem.ncbi.nlm.nih.gov/compound/triethylamine#section=Dissociation-Constants; (ac) https://pubchem.ncbi.nlm.nih.gov/compound/diethylamine#section=Dissociation-Constants; (ad) https://pubchem.ncbi.nlm.nih.gov/compound/piperidine#section=Dissociation-Constants; (ae) https://pubchem.ncbi.nlm.nih.gov/compound/guanidine#section=pK_a.References to publications with the chemical names of the determined compounds (original and corrected ones if necessary): (1) Senthil Kumar et al. (1999 ): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (1:1)]; (2) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (3) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (4) Smith et al. (2003a ): 4-cyanopyridinium 3,5-dinitrosalicylate, 4-cyanopyridinium 3,5-dinitrosalicylate 2-carboxy-4,6-dinitrophenolate; (5) Smith et al. (2011 ): 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (6) Khan et al. (2013 ): 2-aminoanilinium 2-hydroxy-3,5-dinitrobenzoate, 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (7) Jin et al. (2013 ): 3-carbamoylpyridinium 2-carboxy-4,6-dinitrophenolate, 3-carbamoylpyridinium 2-hydroxy-3,5-dinitrobenzoate; (8) Smith et al. (2007): 1-naphthylammonium 3,5-dinitrosalicylate, 1-naphthylammonium 2-carboxy-4,6-dinitrophenolate; (9) Smith et al. (2001b ): 8-aminoquinolinium 3,5-dinitrosalicylate; (10) Smith et al. (2011): 4-chloroanilinium 2-hydroxy-3,5-dinitrobenzoate; (11) Jones et al. (2014 ): (4-iodoanilinium 2-hydroxy-3,5-dinitrobenzoate; (12) Smith et al. (2007): 1,10-Phenanthrolinium 3,5-dinitrosalicylate; (13) Singh et al. (2014 ): 2-(pyridin-2-yl)pyridinium 2-hydroxy-3,5-dinitrobenzoate; (14) Song et al. (2007): 2,2′-bipyridinium 2-carboxy-4,6-dinitrophenolate; (15) Smith et al. (2007): 2,2′-bipyridinium 2-carboxy-4,6-dinitrophenolate; (16) Smith et al. (2005a ): cytosinium 3,5-dinitrosalicylate, cytosinium 2-carboxy-4,6-dinitrophenolate; (17) Smith et al. (2011): anilinium 2-hydroxy-3,5-dinitrobenzoate; (18) Smith et al. (2011): 4-fluoroanilinium 2-hydroxy-3,5-dinitrobenzoate; (19) Smith et al. (2007): quinolinium 3,5-dinitrosalicylate, quinolinium 2-carboxy-4,6-dinitrophenolate; (20) Smith et al. (1995 ): 3,5-dinitrosalicylic acid 2-aminobenzoic acid, 2-ammoniumbenzoic acid 2-carboxy-4,6-dinitrophenolate; (21) Smith et al. (2003a): pyridinium 3,5-dinitrosalicylate 3,5-dinitrosalicylic acid; (22) Zhang et al. (2014 ): 2-methylquinolinium 2-hydroxy-3,5-dinitrobenzoate; (23) Gao et al. (2015 ): 2,6-diaminopyridin-1-ium 2-hydroxy-3,5-dinitrobenzoate; (24) Smith et al. (2003a): 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol solvate, 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol (2:2:1); (25) Jin et al. (2015b ): 1H-imidazol-3-ium 2-carboxy-4,6-dinitrophenolate; (26) Fu et al. (2015 ): hydrazinium 2-carboxy-4,6-dinitrophenolate; (27) Wei et al. (2012): (3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate); (28) this work: (3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate; (29) Smith et al. (2002b ): benzylammonium 3,5-dinitrosalicylate, benzylammonium 2-carboxy-4,6-dinitrophenolate; (30) Jin et al. (2015a ): benzylammonium 2-carboxy-4,6-dinitrophenolate; (31) Smith et al. (2003b ): (S)-(−)-1-phenylethylaminium 3,5-dinitrosalicylate, (S)-(−)-1-phenylethylaminium 2-carboxy-4,6-dinitrophenolate; (32) Ng et al. (2001 ): dicyclohexylammonium 2-carboxy-4,6-dinitrophenolate; (33) Smith et al. (2001c ): 4-ammoniobenzenesulfonamide 3,5-dinitrosalicylate, 4-ammoniobenzenesulfonamide 2-carboxy-4,6-dinitrophenolate; (34) Smith et al. (2002a ): methylammonium 3,5-dinitrosalicylate, methylammonium 2-carboxy-4,6-dinitrophenolate; (35) Smith et al. (2002a): triethylammonium 3,5-dinitrosalicylate; (36) Rajkumar & Chandramohan (2017 ): triethylammonium 2-hydroxy-3,5-dinitrobenzoate; (37) Smith et al. (2005b ): diethylammonium 3,5-dinitrosalicylate, diethylammonium 2-carboxy-4,6-dinitrophenolate; (38) Smith et al. (2006 ): tris(piperidinium) bis(3,5-dinitrosalicylate) monohydrate, tris(piperidinium) 2-hydroxy-3,5-dinitrobenzoate 2-olate-3,5-dinitrobenzoate monohydrate; (39) Smith et al. (2001a ): guanidinium 3,5-dinitrosalicylate; (40) Fu et al. (2015): guanidinium 3,5-dinitrosalicylate.

Figure 3
The dependence of distances: (a) D13 on (q1 + q2); (b) D13 on D2 − D1; (c) D13 on D12—D11; (d) D2 − D1 on (q1 + q2); (e) D13 on (q1 + q2), also for the structures with 3,5-dinitro-2-oxidobenzoate (IV), which are shown as blue triangles. Colour code for symbols: green triangles refer to the structures with 2-hydroxy-3,5-dinitrobenzoic acid (I), black squares are the structures with 2-hydroxy-3,5-dinitrobenzoate (II), and red circles are the structures with 2-carboxy-4,6-dinitrophenolates (III).

Fig. 3a and 3b also show that the bridging hydrogen cannot be situated near the centre of the intramolecular O⋯O hydrogen bond in structures with 2-hydroxy-3,5-dinitrobenzoic acid (I). Fig. 3c shows a similar dependence of D13 on (D12 − D11). It can be seen that the adjacent C—C conjugated bonds are less, but still sensitive to the bonding of the hydroxy hydrogen atom to one of the neighbouring C—O groups. These properties indicate that the O⋯H⋯O hydrogen bonding with the pertinent O⋯O distance D13 belongs to the category of resonance-assisted hydrogen bonds (Gilli et al., 1989, 2009; Sobczyk et al., 2005 ).

Fig. 3d compares both dependences shown in Figs. 3a and 3b. It can be seen that the dependence of (D2 − D1) on (q1 + q2) is fairly linear. The dependence seems to show the narrowest spread for the 2-hydroxy-3,5-dinitrobenzoates (II), which are represented by the black squares. Importantly, the line for each class of molecules intercepts the D2 − D1 axis at different values. The structures that contain 2-hydroxy-3,5-dinitrobenzoic acid (I) molecules (green triangles) are clearly separated from the rest of the structures although they show a similar trend. Figs. 3a–3d also show outliers that do not fit the overall trends and which are most probably the structures determined as 2-hydroxy-3,5-dinitrobenzoates (II) instead of 2-carboxy-4,6-dinitrophenolates (III) and vice versa. Fig. 3e shows the same as Fig. 3a except for the addition of a few known structures that contain a 3,5-dinitro-2-oxidobenzoate (IV), which are indicated by blue triangles. Their positions can be explained by the fact that the carboxylate groups are substantially inclined to the benzene ring in such compounds, which causes elongation of the distance between the carboxylate and oxo group, and these molecules will not be considered further.

The alternation of the inclinations (Fig. 4a–4d) of the dependences of D1, D12, D11, and D2 on (q1 + q2) are in agreement with the delocalization of the electron density in these bonds. The 2-hydroxy-3,5-dinitrobenzoic acid (I) molecules (green triangles) and the 2-hydroxy-3,5-dinitrobenzoates (II; black squares) are situated apart from the 2-carboxy-4,6-dinitrophenolates (III; red circles) in the given figures. The fact that D1 tends to be shortest in 2-hydroxy-3,5-dinitrobenzoic acid (I) molecules (Fig. 4a) can be explained by the elongation of bond D5 in the latter molecules because of the attachment of the hydrogen atom and the concomitant shortening of D1. The bond lengths D1 (Fig. 4a) are equal to 1.28–1.30 Å at (q1 + q2) ≃ 0.08 where the highest probability for the occurrence of a symmetric intramolecular O⋯H⋯O hydrogen bond takes place. The corresponding values of D12, D11, D2, D6 and D10 are 1.49 Å (Fig. 4b), 1.43 Å (Fig. 4c), 1.30 Å (Fig. 4d), 1.37–1.39 Å (Fig. 4e) and 1.41–1.43 Å (Fig. 4f).

Figure 4
The dependence of bond distances: (a) D1 on (q1 + q2); (b) D12 on (q1 + q2); (c) D11 on (q1 + q2); (d) D2 on (q1 + q2); (e) D6 on (q1 + q2); (f) D10 on (q1 + q2). The colour code for the symbols is the same as in Fig. 3

Fig. 5a shows the dependence of D5 on (q1 + q2). Comparing Fig. 5a to Fig. 4a, which shows the dependence of D1 on (q1 + q2), an indirect proportionality of both dependences can be observed. The bond length D5 is equal to 1.22–1.24 Å for (q1 + q2) ≃ 0.08 Å. The dependence of D5 on (q1 + q2) (Fig. 5a) is similar to that of bond D12 (Fig. 4b) in 2-hydroxy-3,5-dinitrobenzoates (II) and 2-carboxy-4,6-dinitrophenolates (III), but not in molecules of 2-hydroxo-3,5-dinitrobenzoic acid (I). It is interesting that 2-hydroxy-3,5-dinitrobenzoic acid (I) molecules are in line with other forms of the title molecules for the dependences in Fig. 5c and Fig. 4d. Bond D7 is rather distant from the carboxylic group (Fig. 5b) and the delocalization within the pyridine ring is no longer clear. The same holds for bonds D14 and D15 (Figs. 5c and 5d). Figs. 5e and 5f show the inclinations, ANG1 and ANG2, of the nitro groups involving bonds D14 and D15, respectively, toward the ring plane.

Figure 5
The dependence of bond distances: (a) D5 on (q1 + q2); (b) D7 on (q1 + q2); (c) D14 on (q1 + q2). The dependence of dihedral angles: (e) ANG1 on (q1 + q2); (f) ANG2 on (q1 + q2). [ANG1 and ANG2 are the dihedral angles of the nitro groups involving bonds D14 and D15, respectively, toward the ring plane.] The colour code of the symbols is the same as in Fig. 3

Fig. 6a–6c show dependences in which the localization of the bridging hydrogen takes place. It seems that the most obtuse angles of O⋯H⋯O (ANG3) occur for (q1 + q2) in the range <0.06–0.10> Å, i.e. for the shortest distances of D13 (2.41 Å). It is questionable whether the position of a bridging hydrogen in the transition zone between 2-hydroxy-3,5-dinitrobenzoates (II) and 2-carboxy-4,6-dinitrophenolates (III) facilitates its positional disorder, which occurs e.g. in NUQVEB, because of the impossibility of angle ANG3 approaching 180°. The dependence of the angles ANG4 and ANG5 (Fig. 1b) shows once more the effect of incorrectly applied constraints, which are manifested by values close to 109.54° (cf. Figs. 2a and 2b).

Figure 6
(a) Dependence of the O⋯H⋯O angle ANG3 on (q1 + q2); (b) dependence of ANG4 on (q1 + q2); (c) dependence of ANG5 on (q1 + q2). Colour code for symbols: green triangles refer to the structures with 2-hydroxy-3,5-dinitrobenzoic acid (I), black squares are the structures with 2-hydroxy-3,5-dinitrobenzoate (II), and red circles are the structures with 2-carboxy-4,6-dinitrophenolate (III); blue triangles, squares and circles are the recalculated structures with 2-hydroxy-3,5-dinitrobenzoic acid (I), 2-hydroxy-3,5-dinitrobenzoate (II) and 2-carboxy-4,6-dinitrophenolate (III), respectively.

The previous discussion has shown the correlations of D1 and D5 on (q1 + q2) (Figs. 4a and 5a, respectively), and the indirect dependence of D1 on D5. Therefore, the position of the bridging hydrogen is expected to be related to the environment of the molecules, i.e. to be dependent on ΔpK_a = pK_a(base) − pK_a(acid). The value of ΔpK_a is correlated with the occurrence of a structure where the base and the acid components are not ionized, thus forming a co-crystal (Δ < 0), or ionized forming a salt (ΔpK_a > 3) (Childs et al., 2007 ). It is difficult to predict the form in which the acid and the base are present for 0 < ΔpK_a < 3 (Childs et al., 2007).

In Table 4, the structures are ordered according to ascending values of the pK_a values of the bases, i.e. according to increasing basicity. The corresponding values of ΔpK_a are compared with (q1 + q2) and D13. The pK_a of 2-hydroxy-3,5-dinitrobenzoic acid (I; 3,5-dinitrosalicylic acid) is reported as 2.18 (Smith & Wermuth, 2014 ; Hemamalini & Fun, 2010a), although a value of 1.53 has been reported in the literature (https://www.chemicalbook.com/ProductMSDSDetailCB9172047_EN.htm). The weakest bases given at the top of Table 4 are not able to deprotonate the title molecule, which remains in the form of 2-hydroxy-3,5-dinitrobenzoic acid (I). On the other hand, the bases with the largest values of pK_a (see the bottom of Table 3) are able to deprive the title molecule of the hydroxy and acid hydrogen atoms, so in such cases the resulting molecule would be in the form of 3,5-dinitro-2-oxidobenzoate (IV). The compounds with moderate basicities are able to deprotonate the acid hydrogen atom but not the bridging hydrogen; hence, the resulting forms are 2-hydroxy-3,5-dinitrobenzoate (II) or 2-carboxy-4,6-dinitrophenolate (III). These structures appear in the intermediate region of Table 4. A more radical transfer of the acid hydrogen atom should cause a more significant shortening of bond D5, which should be concomitant with the elongation of bond D1. Such an elongation of bond D1 (cf. Fig. 1a) should support the formation of a 2-carboxy-4,6-dinitrophenolate (III).

4. Summary

(1) The bridging hydrogen in the molecules discussed (I–III) is involved in a resonance-assisted hydrogen bond, which is part of a hexagonal R₁¹(6) ring. The system of conjugated bonds in the title molecules, however, comprises more atoms than the ring in which the bridging hydrogen is involved. In particular, the whole carboxylate/carboxylic group affects the discussed intramolecular O⋯H⋯O hydrogen bond.

(2) The transition region between the forms of 2-hydroxy-3,5-dinitrobenzoates (II) and 2-carboxy-4,6-dinitrophenolates (III) takes place for C—O (D1) ≃ 1.28–1.30 Å, C—O (D2) ≃ 1.30 Å, O⋯O distance D13 ≃ 2.41 Å and (q1 + q2) ≃ 0.08 Å. Simultaneously, the highest probability for the presence of the bridging hydrogen to be in the centre of the hydrogen bond is expected in this transition region. However, the hydrogen atom can also be disordered over two positions as occurs in NUQVEB.

(3) The bridging hydrogen in the discussed intramolecular hydrogen bond can be situated at the centre between both oxygen atoms with approximately equal C—O bond distances. Therefore, the bridging hydrogen can not be situated at the centre of the intramolecular O⋯H⋯O hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid (I).

(4) In some rare cases (e.g. recalculated SEDKET, KEZJIJ and KEZJIJ01), the bridging hydrogen is bonded to the oxygen atom that forms the shorter C—O bond distance (Table 3). It would be of interest to see how the localization of the bridging hydrogen develops with changing temperature in such cases.

(5) Table 4 shows the occurrence of the different forms of the molecules (see scheme) and the dependence on basicity. Alhough it would be expected that the increasing basicity should support the occurrence of 2-carboxy-4,6-dinitrophenolates (III) and, of course, for very strong bases, 3,5-dinitro-2-oxidobenzoates (IV), there are many exceptions to this rule.

(6) The positioning of the hydrogen atoms can be affected by the asphericity of the electron density of the donor and acceptor atoms.

(7) It is essential to calculate difference electron-density maps in order to locate correctly the bridging hydrogen atom, and any other hydrogen atoms involved in hydrogen bonding.

(8) The present overview has shown that the application of constraints and restraints is frequently incorrect.

Supporting information

CCDC references: 1862187; 1862188; 1862189; 1862190; 1862191; 1862192; 1862193; 1862194; 1862195; 1862196; 1862197; 1862198

Crystal structure: contains datablocks global, DUJZAK, JEVNAA, NUQVEB, QIQJAD, SEDKET, VABZIJ, WADXOR, YAXPOE, LUDFUL, SAFGUD, TIYZIM, TUJPEV. DOI: https://doi.org/10.1107/S2056989018011544/su5452sup1.cif

Structure factors: contains datablock DUJZAK. DOI: https://doi.org/10.1107/S2056989018011544/su5452DUJZAKsup2.hkl

Structure factors: contains datablock JEVNAA. DOI: https://doi.org/10.1107/S2056989018011544/su5452JEVNAAsup3.hkl

Structure factors: contains datablock LUDFUL. DOI: https://doi.org/10.1107/S2056989018011544/su5452LUDFULsup4.hkl

Structure factors: contains datablock NUQVEB. DOI: https://doi.org/10.1107/S2056989018011544/su5452NUQVEBsup5.hkl

Structure factors: contains datablock QIQJAD. DOI: https://doi.org/10.1107/S2056989018011544/su5452QIQJADsup6.hkl

Structure factors: contains datablock SAFGUD. DOI: https://doi.org/10.1107/S2056989018011544/su5452SAFGUDsup7.hkl

Structure factors: contains datablock TIYZIM. DOI: https://doi.org/10.1107/S2056989018011544/su5452TIYZIMsup8.hkl

Structure factors: contains datablock TUJPEV. DOI: https://doi.org/10.1107/S2056989018011544/su5452TUJPEVsup9.hkl

Structure factors: contains datablock VABZIJ. DOI: https://doi.org/10.1107/S2056989018011544/su5452VABZIJsup10.hkl

Structure factors: contains datablock WADXOR. DOI: https://doi.org/10.1107/S2056989018011544/su5452WADXORsup11.hkl

Structure factors: contains datablock YAXPOE. DOI: https://doi.org/10.1107/S2056989018011544/su5452YAXPOEsup12.hkl

Structure factors: contains datablock SEDKET. DOI: https://doi.org/10.1107/S2056989018011544/su5452SEDKETsup13.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452NUQVEBsup14.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452QIQJADsup15.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452SEDKETsup16.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452TIYZIMsup17.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452TUJPEVsup18.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452VABZIJsup19.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452WADXORsup20.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452YAXPOEsup21.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018011544/su5452sup21.pdf

checkCIF report

Computing details top

Data collection: SMART (Bruker, 1997) for DUJZAK; SMART (Bruker, 1999) for JEVNAA; CAD-4 Software (Enraf-Nonius, 1989) for LUDFUL; APEX2 (Bruker, 2009) for NUQVEB, VABZIJ; SMART (Bruker, 2001) for QIQJAD; SMART (Bruker, 2007) for SAFGUD; SMART (Bruker, 2002) for SEDKET; CrysAlis PRO (Agilent, 2012) for TIYZIM; APEX2 (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; APEX2 (Bruker, 2010) for YAXPOE. Cell refinement: SAINT (Bruker, 1997) for DUJZAK; SAINT (Bruker, 1999) for JEVNAA; CAD-4 Software (Enraf-Nonius, 1989) for LUDFUL; SAINT (Bruker, 2009) for NUQVEB, VABZIJ; SAINT (Bruker, 2001) for QIQJAD; SAINT (Bruker, 2007) for SAFGUD; SAINT (Bruker, 2002) for SEDKET; CrysAlis PRO (Agilent, 2012) for TIYZIM; SAINT (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; SAINT (Bruker, 2010) for YAXPOE. Data reduction: SAINT (Bruker, 1997) for DUJZAK; SAINT (Bruker, 1999) for JEVNAA; Xtal3.5 (Hall et al., 1995) for LUDFUL; SAINT (Bruker, 2009) for NUQVEB, VABZIJ; SAINT (Bruker, 2001) for QIQJAD; SAINT (Bruker, 2007) for SAFGUD; SAINT (Bruker, 2002) for SEDKET; CrysAlis RED (Agilent, 2012) for TIYZIM; SAINT (Bruker, 2004) for TUJPEV; CrysAlis PRO (Agilent, 2014) for WADXOR; SAINT (Bruker, 2010) for YAXPOE. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for DUJZAK, JEVNAA, LUDFUL, QIQJAD, SEDKET, TUJPEV, YAXPOE; SHELXTL (Sheldrick, 2008) for NUQVEB, VABZIJ; SHELXS-97 (Sheldrick, 2008) for SAFGUD; SUPERFLIP (Palatinus & Chapuis, 2007) for TIYZIM; SIR92 (Altomare et al., 1993) for WADXOR. Program(s) used to refine structure: JANA2016 (Petricek et al., 2014) for DUJZAK; JANA2006 (Petricek et al., 2014) for JEVNAA, LUDFUL, NUQVEB, QIQJAD, SAFGUD, TIYZIM, TUJPEV, VABZIJ, YAXPOE; JANA2006 (Petricek, 2014) for SEDKET.

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK) top

Crystal data top

[Ag(C₉H₇NO)₂](C₇H₃N₂O₇)	F(000) = 628
M_r = 625.30	D_x = 1.823 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4356 reflections
a = 9.0154 (18) Å	θ = 3.6–27.6°
b = 7.6122 (15) Å	µ = 0.95 mm⁻¹
c = 17.138 (3) Å	T = 293 K
β = 104.38 (3)°	Block, yellow
V = 1139.3 (4) Å³	0.20 × 0.15 × 0.11 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4225 reflections with I > 3σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 27.6°, θ_min = 3.6°
φ and ω scans	h = −11→11
10841 measured reflections	k = −9→8
4602 independent reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.023	Hydrogen site location: difference Fourier map
wR(F) = 0.053	H atoms treated by a mixture of independent and constrained refinement
S = 1.34	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
4602 reflections	(Δ/σ)_max = 0.025
356 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³
48 constraints	Absolute structure: 1800 of Friedel pairs used in the refinement
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (17)

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters 9.

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

	x	y	z	U_iso*/U_eq
Ag1	0.062197 (18)	0.74282 (3)	0.668863 (11)	0.01868 (5)
O1	−0.0993 (2)	0.4630 (2)	0.64021 (12)	0.0202 (6)
O2	0.1741 (2)	0.5061 (2)	0.77196 (12)	0.0214 (6)
N1	−0.1154 (2)	0.7667 (3)	0.55616 (13)	0.0177 (7)
N2	0.2685 (2)	0.8371 (3)	0.75427 (14)	0.0163 (7)
C1	−0.1280 (3)	0.9181 (4)	0.51463 (18)	0.0222 (9)
H1a	−0.061241	1.009276	0.535386	0.0267*
C2	−0.2362 (3)	0.9448 (4)	0.44205 (18)	0.0243 (9)
H2a	−0.240923	1.051917	0.415439	0.0291*
C3	−0.3354 (3)	0.8130 (4)	0.41016 (19)	0.0209 (9)
H3a	−0.407848	0.829471	0.361612	0.0251*
C4	−0.3270 (3)	0.6506 (4)	0.45167 (18)	0.0169 (8)
C5	−0.4264 (3)	0.5079 (4)	0.42259 (17)	0.0209 (9)
H5a	−0.500744	0.518344	0.37429	0.0251*
C6	−0.4131 (3)	0.3554 (4)	0.46539 (17)	0.0217 (9)
H6a	−0.477402	0.261662	0.445311	0.026*
C7	−0.3036 (3)	0.3371 (3)	0.53948 (17)	0.0184 (8)
H7a	−0.297965	0.232672	0.568204	0.0221*
C8	−0.2057 (3)	0.4717 (3)	0.56954 (16)	0.0148 (8)
C9	−0.2139 (3)	0.6331 (3)	0.52566 (16)	0.0141 (8)
C10	0.3159 (3)	0.9993 (4)	0.74633 (17)	0.0188 (9)
H10a	0.256892	1.069872	0.706108	0.0225*
C11	0.4512 (3)	1.0703 (4)	0.79567 (18)	0.0220 (9)
H11a	0.480885	1.184529	0.787703	0.0264*
C12	0.5373 (3)	0.9693 (4)	0.85495 (18)	0.0210 (9)
H12a	0.627346	1.01397	0.887796	0.0252*
C13	0.4907 (3)	0.7960 (3)	0.86712 (16)	0.0171 (8)
C14	0.5743 (3)	0.6845 (4)	0.92853 (17)	0.0200 (8)
H14a	0.665083	0.723938	0.962749	0.024*
C15	0.5225 (3)	0.5197 (4)	0.93771 (17)	0.0206 (8)
H15a	0.577789	0.447807	0.978539	0.0247*
C16	0.3863 (3)	0.4570 (3)	0.88620 (16)	0.0173 (8)
H16a	0.35178	0.344669	0.8937	0.0208*
C17	0.3043 (3)	0.5596 (3)	0.82528 (16)	0.0142 (8)
C18	0.3541 (2)	0.7340 (5)	0.81443 (13)	0.0140 (6)
O3	0.1402 (2)	−0.0134 (3)	0.92525 (13)	0.0259 (7)
O4	−0.4152 (2)	−0.3755 (3)	0.69139 (13)	0.0284 (7)
O5	−0.3271 (2)	−0.5961 (3)	0.76858 (13)	0.0271 (7)
O6	0.1238 (2)	−0.5247 (2)	0.98352 (12)	0.0211 (6)
O7	0.1679 (2)	−0.2659 (4)	1.03546 (11)	0.0286 (6)
O8	−0.0981 (2)	0.1498 (2)	0.70180 (12)	0.0237 (7)
O9	0.06657 (19)	0.2138 (2)	0.81885 (11)	0.0196 (6)
N3	−0.3217 (2)	−0.4436 (3)	0.74764 (14)	0.0173 (7)
N4	0.1088 (2)	−0.3645 (3)	0.98085 (13)	0.0152 (7)
C19	−0.1970 (3)	−0.3339 (4)	0.79254 (18)	0.0130 (8)
C20	−0.1027 (3)	−0.3992 (3)	0.86303 (15)	0.0126 (7)
H20a	−0.114934	−0.512855	0.880295	0.0151*
C21	0.0095 (2)	−0.2908 (3)	0.90660 (15)	0.0114 (8)
C22	0.0326 (3)	−0.1188 (3)	0.88194 (16)	0.0130 (8)
C23	−0.0605 (3)	−0.0603 (3)	0.80708 (16)	0.0129 (7)
C24	−0.1770 (3)	−0.1678 (3)	0.76332 (17)	0.0132 (8)
H24a	−0.240539	−0.128661	0.715089	0.0159*
C25	−0.0307 (3)	0.1145 (3)	0.77245 (16)	0.0148 (8)
H1aa	−0.091407	0.377732	0.663815	0.047 (14)*
H2aa	0.145536	0.395004	0.783901	0.043 (11)*
H3b	0.135279	0.095353	0.887993	0.17 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01622 (8)	0.01722 (9)	0.01945 (10)	−0.00339 (11)	−0.00154 (6)	0.00024 (11)
O1	0.0219 (9)	0.0127 (9)	0.0199 (10)	−0.0063 (8)	−0.0065 (8)	0.0058 (8)
O2	0.0185 (9)	0.0173 (9)	0.0231 (11)	−0.0065 (8)	−0.0049 (8)	0.0030 (8)
N1	0.0190 (9)	0.0152 (14)	0.0181 (11)	−0.0003 (11)	0.0033 (8)	0.0008 (10)
N2	0.0145 (10)	0.0161 (11)	0.0187 (12)	−0.0018 (9)	0.0049 (9)	0.0005 (9)
C1	0.0254 (14)	0.0145 (12)	0.0263 (16)	−0.0042 (12)	0.0056 (12)	0.0044 (11)
C2	0.0325 (15)	0.0177 (13)	0.0239 (16)	0.0069 (13)	0.0093 (12)	0.0104 (11)
C3	0.0214 (13)	0.0247 (13)	0.0154 (15)	0.0059 (12)	0.0021 (12)	0.0023 (11)
C4	0.0136 (12)	0.0220 (14)	0.0150 (15)	0.0026 (11)	0.0031 (10)	0.0005 (12)
C5	0.0160 (12)	0.0289 (15)	0.0156 (14)	0.0005 (12)	−0.0002 (10)	−0.0035 (12)
C6	0.0156 (12)	0.0247 (14)	0.0217 (16)	−0.0092 (12)	−0.0009 (11)	−0.0062 (11)
C7	0.0179 (12)	0.0175 (14)	0.0187 (14)	−0.0039 (11)	0.0026 (10)	0.0018 (11)
C8	0.0139 (12)	0.0146 (12)	0.0140 (13)	0.0001 (11)	0.0000 (9)	−0.0001 (10)
C9	0.0147 (12)	0.0142 (12)	0.0132 (13)	−0.0002 (11)	0.0032 (9)	0.0016 (10)
C10	0.0208 (13)	0.0176 (13)	0.0198 (15)	−0.0021 (12)	0.0084 (11)	0.0021 (11)
C11	0.0259 (14)	0.0166 (13)	0.0254 (16)	−0.0085 (12)	0.0099 (12)	−0.0039 (11)
C12	0.0180 (12)	0.0226 (14)	0.0235 (15)	−0.0108 (12)	0.0074 (11)	−0.0101 (12)
C13	0.0138 (11)	0.0232 (14)	0.0156 (14)	−0.0032 (10)	0.0064 (10)	−0.0059 (10)
C14	0.0118 (11)	0.0285 (14)	0.0182 (15)	−0.0034 (11)	0.0010 (10)	−0.0071 (10)
C15	0.0143 (12)	0.0281 (15)	0.0175 (15)	0.0038 (12)	0.0002 (10)	0.0017 (11)
C16	0.0160 (12)	0.0146 (12)	0.0208 (15)	−0.0018 (11)	0.0035 (10)	−0.0001 (10)
C17	0.0107 (11)	0.0149 (12)	0.0165 (14)	−0.0020 (10)	0.0025 (9)	−0.0031 (10)
C18	0.0115 (9)	0.0160 (11)	0.0156 (11)	0.0014 (17)	0.0052 (8)	0.0001 (15)
O3	0.0215 (10)	0.0236 (11)	0.0279 (12)	−0.0066 (9)	−0.0029 (9)	0.0016 (9)
O4	0.0212 (10)	0.0283 (11)	0.0267 (12)	−0.0044 (9)	−0.0110 (8)	−0.0010 (9)
O5	0.0295 (10)	0.0195 (10)	0.0288 (12)	−0.0130 (9)	0.0004 (9)	0.0016 (9)
O6	0.0213 (9)	0.0158 (9)	0.0236 (11)	0.0028 (8)	0.0007 (8)	0.0059 (8)
O7	0.0340 (9)	0.0225 (9)	0.0194 (9)	0.0057 (15)	−0.0121 (7)	−0.0015 (13)
O8	0.0304 (11)	0.0156 (10)	0.0204 (11)	−0.0061 (9)	−0.0028 (8)	0.0051 (8)
O9	0.0209 (8)	0.0129 (12)	0.0223 (10)	−0.0061 (8)	0.0003 (7)	0.0009 (8)
N3	0.0141 (10)	0.0190 (11)	0.0169 (12)	−0.0064 (10)	0.0001 (9)	−0.0044 (9)
N4	0.0115 (10)	0.0169 (11)	0.0154 (12)	0.0012 (9)	−0.0003 (8)	0.0025 (9)
C19	0.0080 (11)	0.0164 (12)	0.0135 (15)	−0.0043 (10)	0.0009 (10)	−0.0044 (11)
C20	0.0158 (12)	0.0082 (11)	0.0137 (13)	−0.0009 (10)	0.0036 (9)	0.0004 (9)
C21	0.0098 (9)	0.0122 (17)	0.0103 (11)	0.0048 (10)	−0.0012 (8)	0.0021 (9)
C22	0.0086 (11)	0.0150 (13)	0.0147 (14)	−0.0009 (10)	0.0015 (9)	−0.0033 (10)
C23	0.0133 (11)	0.0110 (12)	0.0134 (13)	−0.0001 (10)	0.0015 (9)	−0.0007 (9)
C24	0.0120 (12)	0.0135 (13)	0.0142 (15)	0.0018 (11)	0.0033 (10)	0.0004 (11)
C25	0.0153 (12)	0.0109 (11)	0.0177 (14)	0.0006 (10)	0.0029 (10)	0.0010 (10)

Geometric parameters (Å, º) top

O1—C8	1.347 (3)	C13—C14	1.415 (4)
O1—H1aa	0.7585 (19)	C13—C18	1.415 (3)
O2—C17	1.359 (3)	C14—H14a	0.93
O2—H2aa	0.922 (2)	C14—C15	1.361 (4)
N1—C1	1.344 (4)	C15—H15a	0.93
N1—C9	1.365 (3)	C15—C16	1.406 (3)
N2—C10	1.325 (4)	C16—H16a	0.93
N2—C18	1.371 (4)	C16—C17	1.365 (4)
C1—H1a	0.93	C17—C18	1.429 (5)
C1—C2	1.392 (4)	O3—C22	1.333 (3)
C2—H2a	0.93	O3—H3b	1.040 (2)
C2—C3	1.364 (4)	O4—N3	1.227 (3)
C3—H3a	0.93	O5—N3	1.219 (3)
C3—C4	1.419 (4)	O6—N4	1.226 (3)
C4—C5	1.418 (4)	O7—N4	1.215 (3)
C4—C9	1.423 (4)	O8—C25	1.242 (3)
C5—H5a	0.93	O9—C25	1.275 (3)
C5—C6	1.362 (4)	O9—H3b	1.4952 (19)
C6—H6a	0.93	N3—C19	1.458 (3)
C6—C7	1.408 (4)	N4—C21	1.473 (3)
C7—H7a	0.93	C19—C20	1.385 (4)
C7—C8	1.367 (4)	C19—C24	1.388 (4)
C8—C9	1.433 (4)	C20—H20a	0.93
C10—H10a	0.93	C20—C21	1.373 (3)
C10—C11	1.408 (4)	C21—C22	1.408 (4)
C11—H11a	0.93	C22—C23	1.419 (3)
C11—C12	1.354 (4)	C23—C24	1.394 (3)
C12—H12a	0.93	C23—C25	1.508 (4)
C12—C13	1.416 (4)	C24—H24a	0.93

C8—O1—H1aa	118.2 (2)	C13—C14—C15	120.2 (2)
C17—O2—H2aa	111.60 (19)	H14a—C14—C15	119.88
C1—N1—C9	118.3 (2)	C14—C15—H15a	119.61
C10—N2—C18	118.4 (2)	C14—C15—C16	120.8 (2)
N1—C1—H1a	118.43	H15a—C15—C16	119.61
N1—C1—C2	123.1 (2)	C15—C16—H16a	119.71
H1a—C1—C2	118.43	C15—C16—C17	120.6 (2)
C1—C2—H2a	120.19	H16a—C16—C17	119.71
C1—C2—C3	119.6 (3)	O2—C17—C16	123.8 (2)
H2a—C2—C3	120.19	O2—C17—C18	116.0 (2)
C2—C3—H3a	120.26	C16—C17—C18	120.2 (2)
C2—C3—C4	119.5 (2)	N2—C18—C13	121.8 (3)
H3a—C3—C4	120.27	N2—C18—C17	119.6 (2)
C3—C4—C5	122.8 (2)	C13—C18—C17	118.6 (2)
C3—C4—C9	117.8 (2)	C22—O3—H3b	102.89 (19)
C5—C4—C9	119.5 (2)	C25—O9—H3b	102.84 (17)
C4—C5—H5a	120	O4—N3—O5	124.3 (2)
C4—C5—C6	120.0 (2)	O4—N3—C19	117.5 (2)
H5a—C5—C6	120	O5—N3—C19	118.2 (2)
C5—C6—H6a	119.4	O6—N4—O7	124.2 (2)
C5—C6—C7	121.2 (2)	O6—N4—C21	116.66 (19)
H6a—C6—C7	119.4	O7—N4—C21	119.1 (2)
C6—C7—H7a	119.72	N3—C19—C20	118.7 (2)
C6—C7—C8	120.6 (2)	N3—C19—C24	118.9 (2)
H7a—C7—C8	119.72	C20—C19—C24	122.3 (2)
O1—C8—C7	123.5 (2)	C19—C20—H20a	121.04
O1—C8—C9	116.5 (2)	C19—C20—C21	117.9 (2)
C7—C8—C9	120.0 (2)	H20a—C20—C21	121.04
N1—C9—C4	121.7 (2)	N4—C21—C20	116.7 (2)
N1—C9—C8	119.6 (2)	N4—C21—C22	120.67 (19)
C4—C9—C8	118.7 (2)	C20—C21—C22	122.7 (2)
N2—C10—H10a	118.33	O3—C22—C21	122.3 (2)
N2—C10—C11	123.3 (2)	O3—C22—C23	120.0 (2)
H10a—C10—C11	118.33	C21—C22—C23	117.7 (2)
C10—C11—H11a	120.58	C22—C23—C24	120.0 (2)
C10—C11—C12	118.8 (3)	C22—C23—C25	120.6 (2)
H11a—C11—C12	120.58	C24—C23—C25	119.4 (2)
C11—C12—H12a	119.87	C19—C24—C23	119.2 (2)
C11—C12—C13	120.3 (2)	C19—C24—H24a	120.38
H12a—C12—C13	119.87	C23—C24—H24a	120.38
C12—C13—C14	123.1 (2)	O8—C25—O9	125.0 (2)
C12—C13—C18	117.4 (2)	O8—C25—C23	118.9 (2)
C14—C13—C18	119.6 (3)	O9—C25—C23	116.1 (2)
C13—C14—H14a	119.88	O3—H3b—O9	155.88 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11a···O5ⁱ	0.93	2.48	3.335 (4)	152
O1—H1aa···O8	0.7585 (19)	1.859 (2)	2.606 (3)	167.96 (14)
O2—H2aa···O9	0.922 (2)	1.727 (2)	2.631 (3)	166.48 (15)
O3—H3b···O9	1.040 (2)	1.4952 (19)	2.481 (3)	155.88 (12)

Symmetry code: (i) x+1, y+2, z.

Tetrakis(1H-imidazole-κN³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) top

Crystal data top

[Zn(C₃H₄N₂)₄](C₇H₃N₂O₇)₂	F(000) = 1616
M_r = 791.93	D_x = 1.664 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3242 reflections
a = 25.0809 (15) Å	θ = 2.1–26.9°
b = 6.7251 (4) Å	µ = 0.87 mm⁻¹
c = 18.9145 (10) Å	T = 293 K
β = 97.658 (6)°	Platelet, yellow
V = 3161.9 (3) Å³	0.20 × 0.18 × 0.10 mm
Z = 4

Data collection top

Bruker APEX-II area-detector diffractometer	3635 independent reflections
Radiation source: fine-focus sealed tube	2152 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −32→31
T_min = 0.846, T_max = 0.918	k = −8→8
20634 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.075	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.23	(Δ/σ)_max = 0.007
3635 reflections	Δρ_max = 0.23 e Å⁻³
244 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
32 constraints	Extinction coefficient: 1400 (500)
Primary atom site location: structure-invariant direct methods

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 9

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

	x	y	z	U_iso*/U_eq
C1	0.47960 (10)	0.4200 (3)	0.62639 (13)	0.0460 (10)
H1	0.444004	0.398202	0.633096	0.0552*
C2	0.50386 (10)	0.3369 (4)	0.57533 (13)	0.0484 (10)
H2	0.488745	0.248295	0.540565	0.0581*
C3	0.56018 (9)	0.5299 (3)	0.63970 (12)	0.0401 (9)
H3	0.591591	0.597819	0.656666	0.0481*
C4	0.59325 (9)	0.9065 (4)	0.83991 (12)	0.0404 (9)
H4	0.591722	0.823229	0.87885	0.0485*
N4	0.62879 (7)	1.0508 (3)	0.83789 (11)	0.0471 (8)
C6	0.57665 (9)	1.0451 (4)	0.73735 (13)	0.0444 (9)
H6	0.560952	1.074705	0.691199	0.0533*
C7	0.73999 (9)	0.4553 (3)	0.34225 (11)	0.0329 (8)
C8	0.79245 (9)	0.5059 (3)	0.36676 (12)	0.0342 (8)
H8	0.817639	0.51762	0.335092	0.0411*
C9	0.80717 (8)	0.5388 (3)	0.43803 (12)	0.0311 (8)
C10	0.77048 (8)	0.5210 (3)	0.48978 (12)	0.0302 (8)
C11	0.71702 (8)	0.4593 (3)	0.46099 (11)	0.0282 (7)
C12	0.70286 (9)	0.4300 (3)	0.38898 (12)	0.0323 (8)
H12	0.667845	0.392676	0.371656	0.0388*
C13	0.67545 (9)	0.4249 (3)	0.50834 (12)	0.0333 (8)
N1	0.51487 (7)	0.5429 (3)	0.66784 (9)	0.0373 (7)
N2	0.55523 (8)	0.4075 (3)	0.58408 (10)	0.0438 (8)
N3	0.56024 (7)	0.8957 (3)	0.77961 (9)	0.0354 (7)
C5	0.61854 (9)	1.1406 (4)	0.77303 (14)	0.0479 (10)
H5	0.637064	1.247402	0.75675	0.0575*
N5	0.72386 (8)	0.4225 (3)	0.26644 (10)	0.0427 (8)
N6	0.86351 (7)	0.5897 (3)	0.46068 (11)	0.0403 (8)
O1	0.78238 (6)	0.5518 (2)	0.55681 (8)	0.0378 (6)
O2	0.68832 (6)	0.4695 (2)	0.57640 (8)	0.0420 (6)
O3	0.63104 (6)	0.3579 (2)	0.48669 (8)	0.0426 (6)
O4	0.67630 (7)	0.3835 (3)	0.24643 (8)	0.0575 (7)
O5	0.75772 (7)	0.4340 (3)	0.22570 (9)	0.0662 (8)
O6	0.89634 (7)	0.5475 (3)	0.42013 (9)	0.0658 (8)
O7	0.87622 (6)	0.6730 (3)	0.51757 (9)	0.0568 (7)
Zn1	0.5	0.70908 (6)	0.75	0.03866 (15)
H1a	0.728641	0.508268	0.579335	0.108 (11)*
H2a	0.580668	0.367714	0.552562	0.088 (9)*
H4a	0.657593	1.098579	0.870594	0.106 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0323 (14)	0.0558 (17)	0.0507 (17)	−0.0069 (12)	0.0086 (12)	−0.0071 (13)
C2	0.0460 (16)	0.0536 (18)	0.0448 (17)	−0.0064 (13)	0.0033 (12)	−0.0116 (13)
C3	0.0327 (13)	0.0485 (16)	0.0396 (16)	−0.0053 (11)	0.0071 (11)	0.0037 (12)
C4	0.0366 (14)	0.0491 (16)	0.0343 (15)	0.0066 (12)	0.0004 (11)	0.0062 (12)
N4	0.0332 (12)	0.0568 (15)	0.0484 (15)	−0.0016 (10)	−0.0048 (10)	−0.0044 (11)
C6	0.0416 (15)	0.0568 (17)	0.0336 (15)	−0.0015 (12)	0.0004 (12)	0.0077 (13)
C7	0.0344 (13)	0.0369 (14)	0.0264 (14)	0.0024 (10)	0.0002 (10)	−0.0008 (10)
C8	0.0332 (13)	0.0366 (14)	0.0337 (15)	0.0009 (10)	0.0073 (10)	0.0030 (10)
C9	0.0254 (12)	0.0287 (13)	0.0382 (15)	−0.0031 (9)	0.0003 (10)	−0.0001 (10)
C10	0.0338 (13)	0.0219 (12)	0.0342 (14)	0.0035 (9)	0.0013 (10)	0.0006 (10)
C11	0.0288 (12)	0.0245 (12)	0.0310 (14)	0.0011 (9)	0.0030 (10)	−0.0013 (10)
C12	0.0281 (12)	0.0306 (14)	0.0370 (15)	0.0009 (9)	−0.0002 (10)	0.0004 (10)
C13	0.0338 (13)	0.0312 (14)	0.0356 (15)	0.0037 (10)	0.0067 (11)	−0.0026 (10)
N1	0.0341 (11)	0.0433 (13)	0.0357 (12)	−0.0029 (9)	0.0086 (9)	−0.0001 (9)
N2	0.0437 (12)	0.0526 (14)	0.0371 (13)	0.0034 (10)	0.0126 (10)	−0.0035 (10)
N3	0.0321 (10)	0.0442 (12)	0.0288 (11)	0.0016 (9)	0.0003 (9)	0.0042 (9)
C5	0.0393 (15)	0.0540 (18)	0.0499 (18)	−0.0090 (12)	0.0040 (12)	0.0069 (14)
N5	0.0414 (13)	0.0517 (14)	0.0338 (13)	0.0032 (10)	0.0004 (10)	−0.0005 (10)
N6	0.0327 (11)	0.0435 (13)	0.0438 (14)	−0.0038 (9)	0.0023 (10)	0.0059 (10)
O1	0.0362 (9)	0.0445 (10)	0.0308 (10)	−0.0009 (7)	−0.0026 (7)	−0.0054 (7)
O2	0.0399 (10)	0.0552 (11)	0.0313 (10)	−0.0055 (8)	0.0056 (7)	−0.0066 (8)
O3	0.0325 (9)	0.0561 (11)	0.0400 (10)	−0.0091 (8)	0.0079 (7)	−0.0084 (8)
O4	0.0395 (10)	0.0890 (14)	0.0408 (11)	−0.0047 (9)	−0.0063 (8)	−0.0048 (9)
O5	0.0499 (11)	0.1146 (17)	0.0361 (11)	−0.0057 (10)	0.0133 (9)	−0.0036 (10)
O6	0.0351 (10)	0.1012 (16)	0.0635 (13)	−0.0075 (10)	0.0156 (9)	−0.0121 (11)
O7	0.0430 (10)	0.0799 (14)	0.0453 (11)	−0.0182 (9)	−0.0029 (8)	−0.0108 (10)
Zn1	0.0355 (2)	0.0455 (3)	0.0352 (3)	0	0.00566 (17)	0

Geometric parameters (Å, º) top

C1—H1	0.93	C8—H8	0.93
C1—C2	1.331 (4)	C8—C9	1.367 (3)
C1—N1	1.377 (3)	C9—C10	1.435 (3)
C2—H2	0.93	C9—N6	1.462 (3)
C2—N2	1.362 (3)	C10—C11	1.440 (3)
C3—H3	0.93	C10—O1	1.280 (3)
C3—N1	1.320 (3)	C11—C12	1.375 (3)
C3—N2	1.328 (3)	C11—C13	1.480 (3)
C4—H4	0.93	C12—H12	0.93
C4—N4	1.322 (3)	C13—O2	1.319 (3)
C4—N3	1.319 (3)	C13—O3	1.220 (3)
N4—C5	1.361 (3)	N2—H2a	0.967 (2)
N4—H4a	0.9427 (18)	C5—H5	0.93
C6—H6	0.93	N5—O4	1.231 (3)
C6—N3	1.381 (3)	N5—O5	1.223 (3)
C6—C5	1.335 (3)	N6—O6	1.231 (3)
C7—C8	1.378 (3)	N6—O7	1.217 (3)
C7—C12	1.377 (3)	O1—H1a	1.4955 (15)
C7—N5	1.454 (3)	O2—H1a	1.0386 (15)

H1—C1—C2	124.94	C9—C10—O1	125.18 (18)
H1—C1—N1	124.94	C11—C10—O1	120.2 (2)
C2—C1—N1	110.1 (2)	C10—C11—C12	121.4 (2)
C1—C2—H2	126.81	C10—C11—C13	120.78 (19)
C1—C2—N2	106.4 (2)	C12—C11—C13	117.85 (18)
H2—C2—N2	126.81	C7—C12—C11	120.69 (19)
H3—C3—N1	124.28	C7—C12—H12	119.65
H3—C3—N2	124.28	C11—C12—H12	119.66
N1—C3—N2	111.44 (19)	C11—C13—O2	117.03 (18)
H4—C4—N4	124.35	C11—C13—O3	122.6 (2)
H4—C4—N3	124.35	O2—C13—O3	120.3 (2)
N4—C4—N3	111.3 (2)	C1—N1—C3	104.66 (19)
C4—N4—C5	107.74 (19)	C2—N2—C3	107.4 (2)
C4—N4—H4a	133.8 (2)	C2—N2—H2a	121.3 (2)
C5—N4—H4a	118.5 (2)	C3—N2—H2a	131.3 (2)
H6—C6—N3	125.29	C4—N3—C6	105.04 (18)
H6—C6—C5	125.29	N4—C5—C6	106.5 (2)
N3—C6—C5	109.4 (2)	N4—C5—H5	126.75
C8—C7—C12	120.8 (2)	C6—C5—H5	126.75
C8—C7—N5	119.8 (2)	C7—N5—O4	117.82 (19)
C12—C7—N5	119.40 (19)	C7—N5—O5	119.10 (18)
C7—C8—H8	120.27	O4—N5—O5	123.08 (19)
C7—C8—C9	119.5 (2)	C9—N6—O6	117.66 (19)
H8—C8—C9	120.27	C9—N6—O7	119.73 (19)
C8—C9—C10	123.06 (18)	O6—N6—O7	122.61 (18)
C8—C9—N6	116.8 (2)	C10—O1—H1a	98.67 (13)
C10—C9—N6	120.16 (19)	C13—O2—H1a	102.66 (16)
C9—C10—C11	114.56 (19)	O1—H1a—O2	160.37 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.47	3.327 (3)	154
O2—H1a···C10	1.0386 (15)	2.110 (2)	2.820 (3)	123.5 (1)
O2—H1a···O1	1.0386 (15)	1.4955 (15)	2.498 (2)	160.4 (1)
N2—H2a···O3	0.967 (2)	1.8902 (16)	2.838 (3)	165.87 (12)
N4—H4a···O1ⁱⁱ	0.9427 (18)	1.9236 (14)	2.784 (2)	150.60 (13)
N4—H4a···O7ⁱⁱ	0.9427 (18)	2.4336 (18)	2.873 (3)	108.36 (13)

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

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL) top

Crystal data top

C₇H₄N₂O₇·C₁₂H₈N₂	D_x = 1.556 Mg m⁻³
M_r = 408.33	Melting point: 471 K
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 14.8002 (15) Å	Cell parameters from 25 reflections
b = 7.4029 (16) Å	θ = 5–12°
c = 16.0091 (16) Å	µ = 0.12 mm⁻¹
β = 96.395 (8)°	T = 293 K
V = 1743.1 (5) Å³	Rhombic, yellow
Z = 4	0.36 × 0.34 × 0.26 mm
F(000) = 840

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.056
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 1.5°
Graphite monochromator	h = 0→19
w scans	k = −9→9
8396 measured reflections	l = −21→21
4202 independent reflections	3 standard reflections every 150 reflections
1587 reflections with I > 3σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.083	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.08	(Δ/σ)_max = 0.006
4202 reflections	Δρ_max = 0.29 e Å⁻³
274 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
40 constraints	Extinction coefficient: 5100 (500)
Primary atom site location: structure-invariant direct methods

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 6

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

	x	y	z	U_iso*/U_eq
O3	0.98761 (10)	0.2874 (2)	0.46747 (9)	0.0599 (6)
O1	0.85079 (8)	0.4309 (2)	0.24121 (9)	0.0539 (6)
C1	0.98636 (12)	0.4161 (3)	0.33159 (12)	0.0373 (7)
O7	1.12739 (10)	0.6537 (3)	0.15665 (10)	0.0716 (7)
C4	1.17200 (13)	0.4785 (3)	0.36328 (13)	0.0421 (8)
H4a	1.234071	0.501018	0.373432	0.0506*
C5	1.12429 (13)	0.5256 (3)	0.28746 (12)	0.0378 (7)
O2	0.84456 (9)	0.3110 (2)	0.36758 (9)	0.0632 (7)
C2	1.03254 (14)	0.3661 (3)	0.40995 (13)	0.0430 (8)
C3	1.12654 (13)	0.3980 (3)	0.42348 (12)	0.0423 (8)
N1	1.18089 (15)	0.3455 (3)	0.50174 (12)	0.0665 (9)
C7	0.88704 (14)	0.3818 (3)	0.31414 (14)	0.0457 (9)
C6	1.03232 (13)	0.4947 (3)	0.27113 (12)	0.0386 (7)
H6a	1.001506	0.526882	0.219465	0.0463*
O6	1.25212 (10)	0.6448 (3)	0.23814 (10)	0.0804 (8)
O4	1.14445 (14)	0.2742 (3)	0.55587 (13)	0.1291 (12)
N2	1.17129 (12)	0.6128 (3)	0.22290 (12)	0.0504 (8)
O5	1.26041 (12)	0.3839 (3)	0.51002 (10)	0.0996 (10)
N3	0.68389 (10)	0.3729 (2)	0.18982 (10)	0.0388 (6)
N4	0.50803 (11)	0.3575 (3)	0.10509 (11)	0.0517 (7)
C17	0.57960 (14)	0.2988 (3)	0.06927 (13)	0.0505 (9)
C19	0.61248 (13)	0.4326 (3)	0.22726 (12)	0.0377 (7)
C8	0.74378 (15)	0.2489 (3)	0.06912 (15)	0.0552 (9)
H8a	0.802687	0.252957	0.096215	0.0663*
C16	0.66987 (13)	0.3064 (3)	0.11118 (13)	0.0405 (8)
C18	0.52369 (13)	0.4267 (3)	0.18296 (13)	0.0413 (8)
C12	0.45074 (14)	0.4976 (3)	0.22251 (15)	0.0533 (9)
H12a	0.392387	0.498106	0.194132	0.064*
C14	0.55304 (15)	0.5655 (3)	0.34545 (14)	0.0522 (9)
H14a	0.561295	0.610201	0.400052	0.0627*
C13	0.46523 (15)	0.5645 (3)	0.30108 (15)	0.0555 (10)
H13a	0.416606	0.610633	0.326453	0.0666*
C15	0.62592 (14)	0.5020 (3)	0.30951 (13)	0.0442 (8)
H15a	0.683759	0.504497	0.338918	0.053*
C10	0.6400 (2)	0.1763 (4)	−0.05197 (16)	0.0789 (12)
H10a	0.631177	0.131533	−0.10654	0.0946*
C11	0.56781 (17)	0.2291 (3)	−0.01395 (15)	0.0689 (11)
H11a	0.509671	0.219906	−0.042373	0.0827*
C9	0.72833 (18)	0.1879 (3)	−0.01060 (16)	0.0685 (12)
H9a	0.777245	0.152877	−0.038619	0.0822*
H3a	0.919191	0.279002	0.440153	0.138 (12)*
H1a	0.773139	0.402666	0.229166	0.105 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0634 (10)	0.0734 (13)	0.0442 (9)	−0.0001 (9)	0.0122 (8)	0.0094 (9)
O1	0.0315 (8)	0.0749 (13)	0.0545 (10)	−0.0027 (8)	0.0009 (7)	0.0096 (9)
C1	0.0315 (11)	0.0413 (14)	0.0394 (12)	0.0004 (10)	0.0046 (10)	−0.0033 (11)
O7	0.0556 (10)	0.1066 (17)	0.0520 (10)	−0.0111 (10)	0.0040 (8)	0.0199 (11)
C4	0.0326 (11)	0.0468 (15)	0.0457 (13)	0.0043 (11)	−0.0016 (11)	−0.0111 (12)
C5	0.0325 (11)	0.0414 (15)	0.0398 (12)	0.0028 (10)	0.0059 (10)	−0.0035 (11)
O2	0.0445 (9)	0.0836 (14)	0.0637 (10)	−0.0069 (9)	0.0161 (8)	0.0161 (10)
C2	0.0493 (13)	0.0426 (15)	0.0377 (12)	0.0029 (12)	0.0073 (11)	−0.0033 (12)
C3	0.0449 (12)	0.0468 (16)	0.0337 (12)	0.0128 (11)	−0.0024 (10)	−0.0056 (12)
N1	0.0646 (15)	0.090 (2)	0.0420 (13)	0.0141 (14)	−0.0078 (12)	−0.0014 (13)
C7	0.0413 (13)	0.0461 (16)	0.0509 (14)	−0.0004 (12)	0.0098 (11)	−0.0019 (13)
C6	0.0334 (11)	0.0433 (14)	0.0381 (12)	0.0051 (10)	−0.0003 (10)	−0.0035 (11)
O6	0.0328 (8)	0.1225 (17)	0.0871 (12)	−0.0130 (10)	0.0128 (8)	0.0119 (12)
O4	0.1041 (16)	0.197 (3)	0.0807 (15)	−0.0108 (16)	−0.0151 (13)	0.0758 (17)
N2	0.0369 (11)	0.0590 (15)	0.0567 (13)	−0.0011 (11)	0.0116 (10)	−0.0046 (12)
O5	0.0575 (11)	0.177 (2)	0.0581 (11)	0.0108 (14)	−0.0193 (9)	−0.0056 (13)
N3	0.0310 (9)	0.0431 (12)	0.0419 (10)	−0.0041 (9)	0.0024 (8)	0.0009 (10)
N4	0.0446 (11)	0.0533 (14)	0.0545 (12)	0.0017 (10)	−0.0065 (9)	−0.0035 (11)
C17	0.0538 (14)	0.0491 (17)	0.0469 (14)	0.0046 (13)	−0.0024 (12)	−0.0024 (13)
C19	0.0354 (12)	0.0362 (14)	0.0412 (13)	−0.0040 (11)	0.0029 (10)	0.0023 (11)
C8	0.0564 (15)	0.0521 (18)	0.0588 (16)	0.0030 (13)	0.0136 (13)	−0.0013 (13)
C16	0.0459 (13)	0.0339 (14)	0.0419 (13)	−0.0006 (11)	0.0057 (11)	0.0018 (11)
C18	0.0352 (11)	0.0378 (15)	0.0504 (13)	−0.0009 (11)	0.0032 (10)	−0.0008 (12)
C12	0.0355 (13)	0.0510 (17)	0.0730 (17)	0.0020 (12)	0.0041 (12)	−0.0052 (14)
C14	0.0630 (15)	0.0471 (17)	0.0484 (14)	−0.0037 (14)	0.0143 (13)	−0.0049 (13)
C13	0.0457 (14)	0.0512 (18)	0.0728 (18)	0.0032 (13)	0.0208 (13)	−0.0040 (15)
C15	0.0419 (13)	0.0481 (16)	0.0418 (13)	−0.0029 (12)	0.0012 (11)	0.0047 (12)
C10	0.107 (2)	0.078 (2)	0.0504 (16)	0.009 (2)	0.0051 (17)	−0.0198 (16)
C11	0.0775 (19)	0.071 (2)	0.0533 (17)	0.0057 (16)	−0.0147 (14)	−0.0148 (15)
C9	0.089 (2)	0.060 (2)	0.0602 (18)	0.0060 (17)	0.0270 (15)	−0.0069 (16)

Geometric parameters (Å, º) top

O3—C2	1.329 (3)	N4—C17	1.332 (3)
O3—H3a	1.0592 (14)	N4—C18	1.344 (3)
O1—C7	1.282 (3)	C17—C16	1.428 (3)
O1—H1a	1.1628 (13)	C17—C11	1.421 (3)
C1—C2	1.410 (3)	C19—C18	1.423 (3)
C1—C7	1.487 (3)	C19—C15	1.407 (3)
C1—C6	1.373 (3)	C8—H8a	0.93
O7—N2	1.219 (2)	C8—C16	1.413 (3)
C4—H4a	0.93	C8—C9	1.349 (3)
C4—C5	1.379 (3)	C18—C12	1.412 (3)
C4—C3	1.371 (3)	C12—H12a	0.93
C5—C6	1.376 (3)	C12—C13	1.347 (3)
C5—N2	1.459 (3)	C14—H14a	0.93
O2—C7	1.234 (3)	C14—C13	1.410 (3)
C2—C3	1.404 (3)	C14—C15	1.361 (3)
C3—N1	1.464 (3)	C13—H13a	0.93
N1—O4	1.194 (3)	C15—H15a	0.93
N1—O5	1.204 (3)	C10—H10a	0.93
C6—H6a	0.93	C10—C11	1.346 (4)
O6—N2	1.217 (2)	C10—C9	1.400 (4)
N3—C19	1.346 (3)	C11—H11a	0.93
N3—C16	1.346 (3)	C9—H9a	0.93

C2—O3—H3a	105.60 (13)	C16—C17—C11	117.8 (2)
C7—O1—H1a	113.94 (15)	N3—C19—C18	119.68 (18)
C2—C1—C7	119.58 (18)	N3—C19—C15	120.03 (17)
C2—C1—C6	120.63 (17)	C18—C19—C15	120.28 (19)
C7—C1—C6	119.79 (17)	H8a—C8—C16	120.23
H4a—C4—C5	120.49	H8a—C8—C9	120.23
H4a—C4—C3	120.49	C16—C8—C9	119.5 (2)
C5—C4—C3	119.01 (18)	N3—C16—C17	119.52 (18)
C4—C5—C6	121.58 (19)	N3—C16—C8	120.61 (17)
C4—C5—N2	119.83 (17)	C17—C16—C8	119.86 (19)
C6—C5—N2	118.58 (17)	N4—C18—C19	121.90 (19)
C7—O2—H3a	102.24 (13)	N4—C18—C12	119.74 (18)
O3—C2—C1	120.09 (17)	C19—C18—C12	118.35 (19)
O3—C2—C3	122.05 (17)	C18—C12—H12a	119.82
C1—C2—C3	117.84 (19)	C18—C12—C13	120.35 (19)
C4—C3—C2	121.34 (18)	H12a—C12—C13	119.82
C4—C3—N1	116.79 (18)	H14a—C14—C13	119.52
C2—C3—N1	121.86 (19)	H14a—C14—C15	119.52
C3—N1—O4	119.3 (2)	C13—C14—C15	121.0 (2)
C3—N1—O5	118.0 (2)	C12—C13—C14	121.0 (2)
O4—N1—O5	122.7 (2)	C12—C13—H13a	119.52
O1—C7—C1	115.30 (19)	C14—C13—H13a	119.52
O1—C7—O2	123.93 (18)	C19—C15—C14	119.05 (18)
C1—C7—O2	120.76 (18)	C19—C15—H15a	120.48
C1—C6—C5	119.59 (17)	C14—C15—H15a	120.48
C1—C6—H6a	120.21	H10a—C10—C11	119.51
C5—C6—H6a	120.2	H10a—C10—C9	119.51
O7—N2—C5	118.45 (16)	C11—C10—C9	121.0 (2)
O7—N2—O6	122.87 (19)	C17—C11—C10	120.6 (2)
C5—N2—O6	118.66 (17)	C17—C11—H11a	119.71
C19—N3—C16	119.31 (15)	C10—C11—H11a	119.71
C19—N3—H1a	119.38 (14)	C8—C9—C10	121.3 (3)
C16—N3—H1a	120.79 (14)	C8—C9—H9a	119.37
C17—N4—C18	117.41 (17)	C10—C9—H9a	119.37
N4—C17—C16	122.14 (19)	O3—H3a—O2	151.72 (10)
N4—C17—C11	120.09 (19)	O1—H1a—N3	163.24 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13a···O4ⁱ	0.93	2.49	3.334 (3)	151
O3—H3a···O2	1.0592 (14)	1.5297 (14)	2.5132 (19)	151.72 (10)
O1—H1a···N3	1.1628 (13)	1.4160 (14)	2.5515 (19)	163.24 (10)

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

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB) top

Crystal data top

C₆H₉N₂⁺·C₇H₃N₂O₇⁻	Z = 2
M_r = 336.27	F(000) = 348
Triclinic, P1	D_x = 1.569 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8673 (7) Å	Cell parameters from 5139 reflections
b = 8.0991 (9) Å	θ = 2.7–32.4°
c = 15.2437 (17) Å	µ = 0.13 mm⁻¹
α = 86.844 (3)°	T = 100 K
β = 84.252 (3)°	Block, yellow
γ = 81.209 (3)°	0.29 × 0.14 × 0.08 mm
V = 711.69 (14) Å³

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4943 independent reflections
Radiation source: fine-focus sealed tube	3677 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 32.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.963, T_max = 0.990	k = −12→11
12709 measured reflections	l = −22→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.042	Hydrogen site location: difference Fourier map
wR(F) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 2.06	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
4943 reflections	(Δ/σ)_max = 0.009
222 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³
34 constraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 15

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.50355 (15)	0.28624 (11)	0.24318 (6)	0.0153 (3)
N2	0.82331 (16)	0.41649 (12)	0.19964 (6)	0.0182 (3)
C1	0.67739 (18)	0.36376 (13)	0.26429 (7)	0.0152 (3)
C2	0.35124 (18)	0.22197 (14)	0.30471 (7)	0.0165 (3)
H2	0.233313	0.167725	0.285731	0.0198*
C3	0.36539 (18)	0.23424 (14)	0.39257 (7)	0.0180 (3)
C4	0.54266 (19)	0.31918 (15)	0.41642 (7)	0.0200 (3)
H4	0.556083	0.332079	0.477169	0.024*
C5	0.69461 (19)	0.38301 (14)	0.35491 (7)	0.0186 (3)
H5	0.811136	0.439959	0.372833	0.0223*
C6	0.2014 (2)	0.16274 (17)	0.46143 (8)	0.0262 (4)
H6a	0.118019	0.252439	0.498084	0.0394*
H6b	0.090144	0.110743	0.432458	0.0394*
H6c	0.289083	0.078457	0.498608	0.0394*
O1	0.17284 (13)	0.61818 (10)	0.14277 (5)	0.0201 (2)
O2	0.10549 (15)	0.60964 (11)	0.31689 (5)	0.0252 (3)
O3	0.28472 (15)	0.76461 (12)	0.38855 (5)	0.0275 (3)
O4	0.93312 (14)	0.99538 (11)	0.26216 (6)	0.0242 (3)
O5	0.99966 (15)	1.02486 (11)	0.11988 (6)	0.0279 (3)
O6	0.55543 (14)	0.76370 (11)	−0.07523 (5)	0.0224 (3)
O7	0.26607 (14)	0.63258 (10)	−0.01549 (5)	0.0199 (2)
N3	0.25052 (15)	0.70323 (12)	0.31961 (6)	0.0172 (3)
N4	0.89095 (16)	0.97282 (12)	0.18597 (6)	0.0190 (3)
C7	0.33912 (17)	0.70052 (13)	0.15501 (7)	0.0141 (3)
C8	0.38900 (17)	0.74506 (13)	0.23906 (7)	0.0144 (3)
C9	0.56997 (17)	0.83259 (13)	0.24874 (7)	0.0156 (3)
H9	0.601439	0.859704	0.305724	0.0187*
C10	0.70326 (17)	0.87968 (13)	0.17493 (7)	0.0154 (3)
C11	0.66121 (18)	0.84357 (13)	0.09021 (7)	0.0157 (3)
H11	0.753695	0.879143	0.040052	0.0188*
C12	0.48279 (17)	0.75522 (13)	0.08058 (7)	0.0139 (3)
C13	0.43623 (18)	0.71649 (13)	−0.01006 (7)	0.0165 (3)
H1o7	0.20768	0.615457	0.041923	0.044 (6)*	0.62 (3)
H1o1	0.186813	0.613081	0.081569	0.044 (6)*	0.38 (3)
H2a	0.809476	0.397973	0.143402	0.035 (4)*
H2b	0.928572	0.469891	0.211657	0.048 (5)*
H1	0.481117	0.276133	0.186443	0.032 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0166 (4)	0.0168 (5)	0.0130 (4)	−0.0032 (3)	−0.0023 (3)	−0.0006 (3)
N2	0.0194 (4)	0.0221 (5)	0.0147 (4)	−0.0085 (4)	−0.0004 (3)	−0.0009 (4)
C1	0.0166 (5)	0.0137 (5)	0.0152 (5)	−0.0012 (4)	−0.0022 (4)	−0.0004 (4)
C2	0.0142 (5)	0.0162 (5)	0.0192 (5)	−0.0026 (4)	−0.0015 (4)	−0.0007 (4)
C3	0.0182 (5)	0.0180 (5)	0.0168 (5)	−0.0011 (4)	0.0004 (4)	0.0009 (4)
C4	0.0239 (5)	0.0239 (6)	0.0127 (5)	−0.0043 (5)	−0.0035 (4)	−0.0007 (4)
C5	0.0201 (5)	0.0201 (6)	0.0169 (5)	−0.0054 (4)	−0.0041 (4)	−0.0004 (4)
C6	0.0238 (6)	0.0324 (7)	0.0219 (6)	−0.0077 (5)	0.0028 (4)	0.0047 (5)
O1	0.0192 (4)	0.0259 (4)	0.0176 (4)	−0.0108 (3)	−0.0027 (3)	−0.0010 (3)
O2	0.0275 (4)	0.0281 (5)	0.0220 (4)	−0.0141 (4)	0.0034 (3)	−0.0013 (3)
O3	0.0290 (5)	0.0434 (6)	0.0120 (4)	−0.0097 (4)	−0.0019 (3)	−0.0062 (4)
O4	0.0215 (4)	0.0234 (4)	0.0302 (5)	−0.0036 (3)	−0.0110 (3)	−0.0066 (4)
O5	0.0227 (4)	0.0276 (5)	0.0354 (5)	−0.0122 (4)	−0.0009 (3)	0.0022 (4)
O6	0.0280 (4)	0.0278 (5)	0.0128 (4)	−0.0102 (4)	0.0001 (3)	−0.0006 (3)
O7	0.0229 (4)	0.0252 (4)	0.0139 (4)	−0.0096 (3)	−0.0034 (3)	−0.0010 (3)
N3	0.0168 (4)	0.0200 (5)	0.0145 (4)	−0.0020 (4)	−0.0017 (3)	−0.0002 (4)
N4	0.0154 (4)	0.0150 (5)	0.0275 (5)	−0.0027 (4)	−0.0051 (4)	−0.0025 (4)
C7	0.0135 (4)	0.0136 (5)	0.0150 (5)	−0.0010 (4)	−0.0022 (4)	−0.0010 (4)
C8	0.0145 (5)	0.0155 (5)	0.0128 (5)	−0.0016 (4)	0.0000 (4)	−0.0003 (4)
C9	0.0144 (5)	0.0156 (5)	0.0169 (5)	0.0000 (4)	−0.0038 (4)	−0.0031 (4)
C10	0.0128 (4)	0.0131 (5)	0.0210 (5)	−0.0030 (4)	−0.0035 (4)	−0.0018 (4)
C11	0.0148 (5)	0.0137 (5)	0.0179 (5)	−0.0009 (4)	−0.0007 (4)	−0.0005 (4)
C12	0.0145 (4)	0.0141 (5)	0.0132 (5)	−0.0020 (4)	−0.0018 (4)	−0.0009 (4)
C13	0.0190 (5)	0.0153 (5)	0.0151 (5)	−0.0021 (4)	−0.0026 (4)	−0.0012 (4)

Geometric parameters (Å, º) top

N1—C1	1.3498 (15)	O1—H1o1	0.9310 (8)
N1—C2	1.3674 (14)	O2—N3	1.2280 (14)
N1—H1	0.8977 (9)	O3—N3	1.2338 (13)
N2—C1	1.3353 (14)	O4—N4	1.2402 (14)
N2—H2a	0.8921 (9)	O5—N4	1.2273 (13)
N2—H2b	0.8456 (10)	O6—C13	1.2340 (13)
C1—C5	1.4139 (15)	O7—C13	1.3022 (15)
C2—H2	0.95	O7—H1o7	0.9185 (8)
C2—C3	1.3602 (16)	N3—C8	1.4564 (13)
C3—C4	1.4174 (17)	N4—C10	1.4544 (15)
C3—C6	1.5049 (16)	C7—C8	1.4197 (15)
C4—H4	0.95	C7—C12	1.4357 (14)
C4—C5	1.3643 (16)	C8—C9	1.3874 (16)
C5—H5	0.95	C9—H9	0.95
C6—H6a	0.98	C9—C10	1.3750 (15)
C6—H6b	0.98	C10—C11	1.3934 (16)
C6—H6c	0.98	C11—H11	0.95
H6a—H6b	1.6003	C11—C12	1.3787 (16)
H6a—H6c	1.6003	C12—C13	1.4939 (15)
H6b—H6c	1.6003	H2a—H2b	1.4990 (2)
O1—C7	1.2964 (14)

C1—N1—C2	123.29 (9)	O2—N3—O3	122.52 (9)
C1—N1—H1	120.41 (9)	O2—N3—C8	119.61 (9)
C2—N1—H1	116.29 (10)	O3—N3—C8	117.87 (10)
C1—N2—H2a	120.74 (11)	O4—N4—O5	123.30 (10)
C1—N2—H2b	120.05 (10)	O4—N4—C10	118.02 (9)
H2a—N2—H2b	119.20 (10)	O5—N4—C10	118.69 (10)
N1—C1—N2	118.98 (10)	O1—C7—C8	124.03 (9)
N1—C1—C5	117.27 (9)	O1—C7—C12	119.84 (10)
N2—C1—C5	123.75 (11)	C8—C7—C12	116.12 (10)
N1—C2—H2	119.38	N3—C8—C7	121.67 (10)
N1—C2—C3	121.25 (11)	N3—C8—C9	116.48 (9)
H2—C2—C3	119.38	C7—C8—C9	121.84 (9)
C2—C3—C4	116.54 (10)	C8—C9—H9	120.37
C2—C3—C6	122.15 (11)	C8—C9—C10	119.26 (10)
C4—C3—C6	121.31 (10)	H9—C9—C10	120.37
C3—C4—H4	118.95	N4—C10—C9	118.68 (10)
C3—C4—C5	122.10 (10)	N4—C10—C11	119.25 (9)
H4—C4—C5	118.95	C9—C10—C11	122.05 (10)
C1—C5—C4	119.51 (11)	C10—C11—H11	120.64
C1—C5—H5	120.24	C10—C11—C12	118.72 (9)
C4—C5—H5	120.24	H11—C11—C12	120.64
C3—C6—H6a	109.47	C7—C12—C11	121.98 (10)
C3—C6—H6b	109.47	C7—C12—C13	119.00 (10)
C3—C6—H6c	109.47	C11—C12—C13	119.02 (9)
H6a—C6—H6b	109.47	O6—C13—O7	123.12 (10)
H6a—C6—H6c	109.47	O6—C13—C12	120.31 (10)
H6b—C6—H6c	109.47	O7—C13—C12	116.57 (9)
C7—O1—H1o7	98.33 (6)	O1—H1o7—O7	161.55 (6)
C7—O1—H1o1	101.65 (8)	O7—H1o7—H1o1	166.67 (6)
C13—O7—H1o7	104.71 (9)	O1—H1o1—O7	163.52 (6)
C13—O7—H1o1	99.43 (7)	O1—H1o1—H1o7	171.56 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4ⁱ	0.95	2.47	3.4107 (16)	169
C4—H4···O3ⁱⁱ	0.95	2.38	3.2397 (15)	151
C5—H5···O2ⁱⁱⁱ	0.95	2.43	3.2361 (16)	143
O7—H1o7···O1	0.9185 (8)	1.5313 (8)	2.4202 (12)	161.55 (6)
O1—H1o1···O7	0.9310 (8)	1.5130 (8)	2.4202 (12)	163.52 (6)
N2—H2a···O7^iv	0.8921 (9)	2.0783 (9)	2.9655 (14)	172.84 (6)
N2—H2b···O1ⁱⁱⁱ	0.8456 (10)	2.1644 (9)	2.8526 (14)	138.40 (6)
N2—H2b···O2ⁱⁱⁱ	0.8456 (10)	2.4133 (10)	3.1741 (14)	150.02 (6)
N1—H1···O6^iv	0.8977 (9)	1.7828 (9)	2.6781 (13)	174.83 (6)

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

3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) top

Crystal data top

C₉H₈Cl₂N₅⁺·C₇H₃N₂O₇⁻·C₃H₇NO	Z = 2
M_r = 557.31	F(000) = 572
Triclinic, P1	D_x = 1.564 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0227 (5) Å	Cell parameters from 6413 reflections
b = 10.5507 (5) Å	θ = 2.3–28.2°
c = 12.5359 (6) Å	µ = 0.34 mm⁻¹
α = 81.858 (1)°	T = 294 K
β = 71.888 (1)°	Plate, colourless
γ = 70.009 (1)°	0.16 × 0.14 × 0.08 mm
V = 1183.1 (1) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5507 independent reflections
Radiation source: fine-focus sealed tube	4441 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→13
T_min = 0.93, T_max = 0.97	k = −13→13
13936 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
R[F > 3σ(F)] = 0.056	Secondary atom site location: difference Fourier map
wR(F) = 0.147	Hydrogen site location: difference Fourier map
S = 3.41	H atoms treated by a mixture of independent and constrained refinement
5507 reflections	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
340 parameters	(Δ/σ)_max = 0.020
0 restraints	Δρ_max = 0.80 e Å⁻³
48 constraints	Δρ_min = −0.36 e Å⁻³

Special details top

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

Refinement. Number of fixed parameters: 18

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

	x	y	z	U_iso*/U_eq
C1	0.32107 (18)	1.06764 (19)	0.15844 (16)	0.0464 (7)
C2	0.2718 (2)	1.0232 (2)	0.08378 (15)	0.0485 (7)
C3	0.2713 (2)	1.0903 (2)	−0.02046 (16)	0.0529 (8)
C4	0.3231 (2)	1.2001 (2)	−0.04951 (19)	0.0621 (9)
H4	0.323127	1.245173	−0.11886	0.0745*
C5	0.3741 (2)	1.2420 (2)	0.02358 (19)	0.0632 (10)
H5	0.410127	1.314857	0.001937	0.0758*
C6	0.3745 (2)	1.1807 (2)	0.12857 (17)	0.0537 (8)
H6	0.40816	1.211924	0.177727	0.0645*
C7	0.32753 (18)	0.99894 (19)	0.26974 (15)	0.0437 (7)
C8	0.35068 (19)	0.8912 (2)	0.47363 (15)	0.0449 (7)
C9	0.19780 (18)	0.99408 (18)	0.36291 (15)	0.0418 (7)
N1	0.45735 (16)	0.95248 (17)	0.28531 (13)	0.0488 (6)
N2	0.46755 (16)	0.89842 (17)	0.38722 (13)	0.0484 (6)
N3	0.37354 (18)	0.8352 (2)	0.56859 (14)	0.0613 (8)
N4	0.21299 (15)	0.93978 (16)	0.46191 (12)	0.0454 (6)
N5	0.06397 (16)	1.04599 (17)	0.35102 (13)	0.0504 (7)
Cl1	0.21444 (7)	0.88366 (6)	0.11855 (5)	0.0685 (3)
Cl2	0.20368 (7)	1.04039 (8)	−0.11161 (5)	0.0772 (3)
C10	0.7671 (2)	0.7509 (2)	0.50260 (17)	0.0495 (8)
C11	0.92521 (19)	0.68875 (18)	0.50532 (16)	0.0456 (8)
C12	1.0399 (2)	0.68056 (19)	0.40501 (17)	0.0482 (8)
C13	1.1855 (2)	0.6217 (2)	0.4120 (2)	0.0565 (9)
C14	1.2169 (3)	0.5728 (2)	0.5120 (2)	0.0650 (11)
H14	1.31429	0.535992	0.515021	0.078*
C15	1.1014 (3)	0.5795 (2)	0.6070 (2)	0.0608 (10)
C16	0.9560 (2)	0.63637 (19)	0.60559 (18)	0.0537 (9)
H16	0.879592	0.639442	0.671313	0.0645*
N6	1.3082 (2)	0.6096 (2)	0.3083 (2)	0.0763 (10)
N7	1.1324 (3)	0.5213 (2)	0.7146 (3)	0.0870 (14)
O1	0.74835 (14)	0.79734 (16)	0.40757 (12)	0.0638 (7)
O2	0.66684 (16)	0.75284 (17)	0.58991 (13)	0.0695 (7)
O3	1.01381 (16)	0.72881 (16)	0.30779 (13)	0.0651 (7)
O4	1.3027 (2)	0.5624 (2)	0.22939 (18)	0.0962 (10)
O5	1.4096 (2)	0.6460 (3)	0.3106 (2)	0.1311 (14)
O6	1.2621 (3)	0.4654 (3)	0.7114 (2)	0.1272 (14)
O7	1.0297 (3)	0.5356 (3)	0.7980 (2)	0.1153 (15)
C17	0.8968 (2)	0.2419 (2)	0.13898 (19)	0.0638 (10)
H17	0.997049	0.225753	0.10284	0.0765*
C18	0.6486 (3)	0.3564 (4)	0.1366 (3)	0.1002 (16)
H18a	0.600566	0.362237	0.079827	0.1503*
H18b	0.612084	0.441665	0.171497	0.1503*
H18c	0.628154	0.287766	0.192178	0.1503*
C19	0.8613 (4)	0.3905 (3)	−0.0204 (2)	0.0959 (16)
H19a	0.812684	0.38463	−0.07367	0.1439*
H19b	0.842404	0.483699	−0.008394	0.1439*
H19c	0.965894	0.347377	−0.048929	0.1439*
N8	0.8043 (2)	0.32305 (17)	0.08649 (14)	0.0588 (8)
O8	0.86513 (17)	0.18476 (18)	0.23111 (12)	0.0693 (7)
H3n	0.459992	0.808642	0.579383	0.067 (7)*
H4n	0.300684	0.831649	0.62665	0.058 (6)*
H2n	0.560448	0.867423	0.392878	0.069 (7)*
H5n	−0.01125	1.040769	0.406749	0.056 (6)*
H6n	0.043449	1.086703	0.2906	0.052 (6)*
H3o	0.911378	0.756483	0.330791	0.131 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0300 (8)	0.0541 (11)	0.0483 (10)	−0.0081 (8)	−0.0060 (7)	−0.0055 (8)
C2	0.0354 (9)	0.0578 (11)	0.0464 (10)	−0.0118 (8)	−0.0044 (8)	−0.0068 (8)
C3	0.0364 (9)	0.0682 (13)	0.0443 (10)	−0.0090 (9)	−0.0049 (8)	−0.0047 (9)
C4	0.0457 (11)	0.0737 (15)	0.0546 (12)	−0.0053 (10)	−0.0119 (9)	−0.0038 (11)
C5	0.0580 (13)	0.0599 (13)	0.0701 (14)	−0.0224 (11)	−0.0153 (11)	0.0054 (11)
C6	0.0442 (10)	0.0589 (12)	0.0502 (11)	−0.0107 (9)	−0.0112 (9)	0.0032 (9)
C7	0.0323 (9)	0.0527 (11)	0.0433 (10)	−0.0115 (8)	−0.0076 (7)	−0.0053 (8)
C8	0.0316 (8)	0.0564 (11)	0.0446 (10)	−0.0113 (8)	−0.0096 (7)	−0.0050 (8)
C9	0.0305 (8)	0.0502 (10)	0.0430 (9)	−0.0112 (7)	−0.0074 (7)	−0.0072 (8)
N1	0.0326 (8)	0.0622 (10)	0.0469 (9)	−0.0126 (7)	−0.0079 (6)	−0.0007 (7)
N2	0.0282 (7)	0.0679 (10)	0.0450 (9)	−0.0113 (7)	−0.0098 (6)	−0.0005 (7)
N3	0.0343 (8)	0.0949 (14)	0.0468 (9)	−0.0152 (9)	−0.0110 (7)	0.0078 (9)
N4	0.0293 (7)	0.0618 (10)	0.0417 (8)	−0.0119 (7)	−0.0077 (6)	−0.0027 (7)
N5	0.0307 (7)	0.0730 (11)	0.0421 (9)	−0.0106 (7)	−0.0102 (7)	−0.0001 (8)
Cl1	0.0784 (4)	0.0786 (4)	0.0600 (3)	−0.0419 (3)	−0.0150 (3)	−0.0059 (3)
Cl2	0.0721 (4)	0.1162 (5)	0.0522 (3)	−0.0373 (4)	−0.0190 (3)	−0.0090 (3)
C10	0.0386 (10)	0.0504 (11)	0.0597 (12)	−0.0073 (8)	−0.0180 (9)	−0.0107 (9)
C11	0.0404 (10)	0.0417 (10)	0.0597 (12)	−0.0103 (8)	−0.0219 (9)	−0.0067 (8)
C12	0.0395 (10)	0.0464 (10)	0.0641 (12)	−0.0136 (8)	−0.0218 (9)	−0.0030 (9)
C13	0.0384 (10)	0.0512 (11)	0.0826 (15)	−0.0101 (8)	−0.0220 (10)	−0.0101 (10)
C14	0.0504 (12)	0.0533 (12)	0.1065 (19)	−0.0093 (10)	−0.0465 (13)	−0.0135 (12)
C15	0.0692 (15)	0.0506 (12)	0.0797 (15)	−0.0144 (10)	−0.0492 (13)	−0.0036 (10)
C16	0.0578 (12)	0.0501 (11)	0.0625 (13)	−0.0162 (9)	−0.0287 (10)	−0.0069 (9)
N6	0.0372 (10)	0.0779 (14)	0.1062 (18)	−0.0082 (9)	−0.0156 (10)	−0.0157 (12)
N7	0.113 (2)	0.0759 (15)	0.1066 (19)	−0.0325 (14)	−0.0800 (17)	0.0073 (14)
O1	0.0374 (7)	0.0841 (11)	0.0645 (9)	−0.0093 (7)	−0.0222 (7)	0.0067 (8)
O2	0.0428 (8)	0.0946 (12)	0.0601 (9)	−0.0074 (8)	−0.0121 (7)	−0.0108 (8)
O3	0.0427 (8)	0.0802 (10)	0.0653 (9)	−0.0151 (7)	−0.0148 (7)	0.0074 (8)
O4	0.0575 (10)	0.1277 (17)	0.0882 (13)	−0.0110 (11)	−0.0135 (9)	−0.0195 (12)
O5	0.0520 (11)	0.164 (2)	0.181 (2)	−0.0480 (13)	0.0026 (13)	−0.0623 (18)
O6	0.1283 (19)	0.1273 (18)	0.142 (2)	0.0037 (15)	−0.1080 (17)	−0.0100 (15)
O7	0.142 (2)	0.159 (2)	0.0879 (15)	−0.0849 (19)	−0.0675 (16)	0.0370 (15)
C17	0.0454 (11)	0.0753 (15)	0.0575 (13)	−0.0065 (10)	−0.0078 (10)	−0.0085 (11)
C18	0.0568 (15)	0.129 (3)	0.120 (2)	−0.0180 (16)	−0.0417 (16)	−0.009 (2)
C19	0.123 (3)	0.0831 (19)	0.0697 (17)	−0.0251 (18)	−0.0261 (16)	0.0120 (14)
N8	0.0593 (11)	0.0601 (11)	0.0548 (10)	−0.0096 (9)	−0.0229 (9)	−0.0033 (8)
O8	0.0558 (9)	0.0937 (12)	0.0520 (9)	−0.0195 (8)	−0.0165 (7)	0.0097 (8)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C13—C14	1.374 (4)
C1—C6	1.427 (3)	C13—N6	1.471 (3)
C1—C7	1.488 (3)	C14—H14	0.93
C2—C3	1.396 (3)	C14—C15	1.369 (3)
C3—C4	1.385 (4)	C15—C16	1.378 (3)
C4—H4	0.93	C15—N7	1.479 (4)
C4—C5	1.362 (4)	C16—H16	0.93
C5—H5	0.93	N6—O4	1.192 (4)
C5—C6	1.382 (3)	N6—O5	1.213 (4)
C6—H6	0.93	N7—O6	1.221 (4)
C7—C9	1.464 (2)	N7—O7	1.202 (4)
C7—N1	1.291 (2)	O3—H3o	0.9258 (14)
C8—N2	1.342 (2)	C17—H17	0.93
C8—N3	1.303 (3)	C17—N8	1.305 (3)
C8—N4	1.345 (2)	C17—O8	1.226 (3)
C9—N4	1.322 (2)	C18—H18a	0.96
C9—N5	1.312 (2)	C18—H18b	0.96
N1—N2	1.343 (2)	C18—H18c	0.96
N2—H2n	0.8973 (16)	C18—N8	1.425 (3)
N3—H3n	0.8624 (18)	H18a—H18b	1.5677
N3—H4n	0.8630 (15)	H18a—H18c	1.5677
N5—H5n	0.8658 (14)	H18b—H18c	1.5677
N5—H6n	0.8630 (16)	C19—H19a	0.96
C10—C11	1.503 (3)	C19—H19b	0.96
C10—O1	1.267 (3)	C19—H19c	0.96
C10—O2	1.231 (2)	C19—N8	1.470 (3)
C11—C12	1.405 (2)	H19a—H19b	1.5677
C11—C16	1.382 (3)	H19a—H19c	1.5677
C12—C13	1.402 (3)	H19b—H19c	1.5677
C12—O3	1.321 (3)

C2—C1—C6	120.20 (18)	C11—C12—O3	122.09 (17)
C2—C1—C7	122.86 (19)	C13—C12—O3	120.57 (17)
C6—C1—C7	116.9 (2)	C12—C13—C14	122.17 (18)
C1—C2—C3	120.2 (2)	C12—C13—N6	118.7 (2)
C2—C3—C4	119.6 (2)	C14—C13—N6	119.10 (19)
C3—C4—H4	120.02	C13—C14—H14	120.79
C3—C4—C5	120.0 (2)	C13—C14—C15	118.4 (2)
H4—C4—C5	120.02	H14—C14—C15	120.79
C4—C5—H5	118.63	C14—C15—C16	122.1 (2)
C4—C5—C6	122.7 (2)	C14—C15—N7	119.4 (2)
H5—C5—C6	118.63	C16—C15—N7	118.5 (2)
C1—C6—C5	117.3 (2)	C11—C16—C15	119.19 (18)
C1—C6—H6	121.37	C11—C16—H16	120.41
C5—C6—H6	121.36	C15—C16—H16	120.41
C1—C7—C9	124.50 (16)	C13—N6—O4	118.2 (2)
C1—C7—N1	115.60 (15)	C13—N6—O5	117.0 (3)
C9—C7—N1	119.58 (16)	O4—N6—O5	124.8 (2)
N2—C8—N3	118.61 (17)	C15—N7—O6	116.6 (2)
N2—C8—N4	120.57 (17)	C15—N7—O7	118.1 (3)
N3—C8—N4	120.81 (16)	O6—N7—O7	125.3 (3)
C7—C9—N4	120.53 (16)	C10—O1—H3o	101.27 (12)
C7—C9—N5	120.93 (16)	C12—O3—H3o	99.28 (14)
N4—C9—N5	118.52 (15)	H17—C17—N8	116.69
C7—N1—N2	117.85 (14)	H17—C17—O8	116.69
C8—N2—N1	123.77 (16)	N8—C17—O8	126.6 (2)
C8—N2—H2n	122.42 (17)	H18a—C18—H18b	109.47
N1—N2—H2n	113.82 (14)	H18a—C18—H18c	109.47
C8—N3—H3n	122.28 (17)	H18a—C18—N8	109.47
C8—N3—H4n	121.07 (18)	H18b—C18—H18c	109.47
H3n—N3—H4n	116.2 (2)	H18b—C18—N8	109.47
C8—N4—C9	117.69 (14)	H18c—C18—N8	109.47
C9—N5—H5n	119.55 (17)	H19a—C19—H19b	109.47
C9—N5—H6n	124.81 (16)	H19a—C19—H19c	109.47
H5n—N5—H6n	115.64 (18)	H19a—C19—N8	109.47
C11—C10—O1	115.76 (15)	H19b—C19—H19c	109.47
C11—C10—O2	119.27 (19)	H19b—C19—N8	109.47
O1—C10—O2	124.96 (19)	H19c—C19—N8	109.47
C10—C11—C12	119.51 (18)	C17—N8—C18	120.7 (2)
C10—C11—C16	119.71 (16)	C17—N8—C19	119.5 (2)
C12—C11—C16	120.74 (18)	C18—N8—C19	119.6 (2)
C11—C12—C13	117.3 (2)	O1—H3o—O3	161.33 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19a···O4ⁱ	0.96	2.47	3.401 (4)	163
N3—H3n···O2	0.8624 (18)	1.9939 (16)	2.854 (2)	174.78 (11)
N3—H4n···O8ⁱⁱ	0.8630 (15)	2.0586 (14)	2.921 (2)	176.91 (12)
N2—H2n···O1	0.8973 (16)	1.8310 (15)	2.728 (2)	177.45 (12)
N5—H5n···N4ⁱⁱⁱ	0.8658 (14)	2.1409 (13)	2.9992 (19)	171.06 (11)
N5—H6n···O8^iv	0.8630 (16)	2.0412 (16)	2.760 (2)	140.22 (10)
O3—H3o···O1	0.9258 (14)	1.5621 (12)	2.4572 (18)	161.33 (12)

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

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) top

Crystal data top

[Ag(C₁₂H₆N₂O₂)](C₇H₃N₂O₇)	F(000) = 1512
M_r = 755.36	D_x = 1.817 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5197 reflections
a = 11.757 (2) Å	θ = 3.2–25.4°
b = 18.297 (4) Å	µ = 0.81 mm⁻¹
c = 13.223 (3) Å	T = 174 K
β = 103.91 (3)°	Prism, yellow
V = 2761.1 (11) Å³	0.3 × 0.24 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	5013 independent reflections
Radiation source: fine-focus sealed tube	3100 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 25.4°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→11
T_min = 0.780, T_max = 0.910	k = −17→22
12726 measured reflections	l = −15→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F > 3σ(F)] = 0.062	H-atom parameters constrained
wR(F) = 0.118	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.64	(Δ/σ)_max = 0.016
5013 reflections	Δρ_max = 0.76 e Å⁻³
444 parameters	Δρ_min = −0.63 e Å⁻³
0 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
56 constraints	Extinction coefficient: 2400 (800)
Primary atom site location: structure-invariant direct methods

Special details top

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters 3

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

	x	y	z	U_iso*/U_eq
Ag1	0.21070 (4)	0.44031 (3)	0.52479 (4)	0.0538 (2)
C1	0.4796 (5)	0.5138 (3)	0.6221 (4)	0.043 (2)
H1	0.440696	0.558209	0.60689	0.0511*
C2	0.5975 (6)	0.5153 (3)	0.6692 (4)	0.046 (2)
H2	0.637009	0.559483	0.684873	0.0553*
C3	0.6551 (5)	0.4500 (3)	0.6925 (4)	0.046 (2)
H3	0.734391	0.449118	0.725729	0.0547*
C4	0.5946 (5)	0.3859 (3)	0.6661 (4)	0.035 (2)
C5	0.6523 (8)	0.3141 (4)	0.6884 (5)	0.068 (3)
C6	0.5912 (10)	0.2510 (4)	0.6718 (6)	0.093 (5)
C7	0.4628 (6)	0.2534 (3)	0.6228 (4)	0.042 (2)
C8	0.3994 (7)	0.1881 (3)	0.6033 (4)	0.052 (3)
H8	0.435089	0.143184	0.6224	0.0623*
C9	0.2837 (7)	0.1928 (4)	0.5555 (5)	0.063 (3)
H9	0.238665	0.150616	0.540161	0.0756*
C10	0.2345 (6)	0.2592 (3)	0.5304 (5)	0.052 (3)
H10	0.155582	0.26107	0.496188	0.0629*
C11	0.4065 (5)	0.3197 (3)	0.5966 (4)	0.032 (2)
C12	0.4742 (5)	0.3885 (3)	0.6197 (4)	0.033 (2)
C13	0.0851 (5)	0.4150 (3)	0.2774 (5)	0.054 (3)
H13	0.109147	0.367048	0.293174	0.0649*
C14	0.0376 (5)	0.4324 (4)	0.1743 (5)	0.060 (3)
H14	0.029151	0.397085	0.122358	0.0717*
C15	0.0032 (5)	0.5033 (3)	0.1508 (5)	0.051 (3)
H15	−0.030371	0.516779	0.082274	0.0617*
C16	0.0190 (5)	0.5550 (3)	0.2306 (4)	0.040 (2)
C17	−0.0145 (5)	0.6317 (3)	0.2063 (5)	0.051 (3)
C18	−0.0094 (5)	0.6826 (3)	0.2940 (5)	0.053 (3)
C19	0.0474 (5)	0.6578 (3)	0.4023 (5)	0.042 (2)
C20	0.0689 (5)	0.7058 (3)	0.4858 (5)	0.052 (3)
H20	0.048099	0.754726	0.475014	0.063*
C21	0.1204 (6)	0.6817 (4)	0.5833 (5)	0.058 (3)
H21	0.134626	0.713123	0.64029	0.0692*
C22	0.1503 (5)	0.6091 (4)	0.5941 (5)	0.054 (3)
H22	0.186352	0.59254	0.660553	0.0653*
C23	0.0818 (5)	0.5847 (3)	0.4195 (4)	0.036 (2)
C24	0.0637 (4)	0.5318 (3)	0.3326 (4)	0.032 (2)
C25	0.6150 (6)	0.4142 (3)	0.9276 (4)	0.041 (2)
C26	0.5079 (6)	0.4527 (3)	0.8869 (4)	0.040 (2)
C27	0.4074 (5)	0.4101 (3)	0.8426 (4)	0.037 (2)
C28	0.4091 (5)	0.3351 (3)	0.8456 (4)	0.041 (2)
H28	0.341998	0.308064	0.817616	0.0498*
C29	0.5156 (6)	0.3004 (3)	0.8924 (4)	0.041 (2)
C30	0.6177 (5)	0.3387 (3)	0.9323 (4)	0.043 (2)
H30	0.687051	0.314123	0.961804	0.0515*
C31	0.2956 (6)	0.4467 (4)	0.7881 (5)	0.047 (3)
N1	0.4179 (4)	0.4525 (2)	0.5968 (3)	0.0338 (17)
N2	0.2929 (4)	0.3229 (2)	0.5519 (3)	0.0387 (18)
N3	0.0989 (4)	0.4627 (2)	0.3563 (3)	0.0413 (18)
N4	0.1317 (4)	0.5603 (2)	0.5163 (3)	0.0405 (18)
N5	0.7267 (6)	0.4510 (4)	0.9628 (4)	0.059 (3)
N6	0.5168 (6)	0.2209 (3)	0.9002 (4)	0.055 (3)
O1	0.7646 (5)	0.3117 (3)	0.7273 (4)	0.092 (3)
O2	0.6406 (5)	0.1892 (3)	0.6987 (4)	0.102 (3)
O3	−0.0421 (4)	0.6544 (2)	0.1169 (3)	0.069 (2)
O4	−0.0501 (5)	0.7444 (2)	0.2776 (4)	0.081 (2)
O5	0.8168 (5)	0.4145 (3)	0.9750 (4)	0.090 (3)
O6	0.7298 (5)	0.5169 (3)	0.9762 (4)	0.084 (2)
O7	0.5025 (4)	0.5233 (2)	0.8850 (3)	0.0617 (19)
O8	0.2936 (4)	0.5168 (3)	0.7945 (3)	0.066 (2)
O9	0.2137 (4)	0.4111 (3)	0.7370 (3)	0.064 (2)
O10	0.4286 (5)	0.1877 (2)	0.8580 (4)	0.070 (2)
O11	0.6096 (5)	0.1916 (2)	0.9512 (4)	0.068 (2)
H7	0.388884	0.531747	0.83591	0.019 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0474 (4)	0.0492 (3)	0.0603 (3)	0.0150 (3)	0.0038 (2)	0.0149 (3)
C1	0.054 (5)	0.035 (4)	0.041 (3)	−0.006 (3)	0.014 (3)	0.001 (3)
C2	0.052 (5)	0.041 (4)	0.048 (4)	−0.010 (3)	0.018 (3)	−0.001 (3)
C3	0.031 (4)	0.063 (4)	0.043 (3)	−0.004 (3)	0.008 (3)	−0.008 (3)
C4	0.036 (4)	0.034 (3)	0.035 (3)	0.015 (3)	0.013 (3)	0.004 (3)
C5	0.085 (7)	0.078 (6)	0.048 (4)	0.014 (5)	0.031 (4)	0.006 (4)
C6	0.201 (12)	0.037 (5)	0.065 (5)	0.012 (6)	0.081 (7)	0.001 (4)
C7	0.033 (4)	0.059 (5)	0.035 (3)	0.007 (3)	0.008 (3)	0.001 (3)
C8	0.088 (6)	0.023 (3)	0.051 (4)	0.010 (4)	0.029 (4)	0.005 (3)
C9	0.074 (6)	0.053 (5)	0.067 (5)	−0.009 (4)	0.025 (4)	−0.008 (4)
C10	0.039 (4)	0.054 (4)	0.064 (4)	−0.003 (4)	0.012 (3)	−0.014 (4)
C11	0.043 (4)	0.026 (3)	0.029 (3)	0.006 (3)	0.010 (3)	0.002 (2)
C12	0.043 (4)	0.031 (3)	0.028 (3)	−0.004 (3)	0.014 (3)	0.002 (2)
C13	0.052 (5)	0.034 (4)	0.071 (5)	−0.002 (3)	0.005 (4)	−0.001 (3)
C14	0.055 (5)	0.055 (5)	0.064 (4)	0.000 (4)	0.003 (4)	−0.024 (4)
C15	0.046 (4)	0.057 (4)	0.045 (4)	−0.004 (3)	0.000 (3)	−0.002 (3)
C16	0.029 (3)	0.038 (3)	0.051 (4)	0.000 (3)	0.004 (3)	0.005 (3)
C17	0.039 (4)	0.054 (4)	0.055 (4)	0.002 (3)	0.001 (3)	0.021 (4)
C18	0.036 (4)	0.042 (4)	0.077 (5)	−0.003 (3)	0.004 (3)	0.005 (4)
C19	0.035 (4)	0.032 (3)	0.057 (4)	0.003 (3)	0.007 (3)	0.002 (3)
C20	0.046 (4)	0.031 (3)	0.079 (5)	0.000 (3)	0.012 (4)	−0.010 (4)
C21	0.049 (5)	0.055 (5)	0.067 (5)	0.002 (4)	0.010 (4)	−0.013 (4)
C22	0.046 (4)	0.070 (5)	0.042 (4)	−0.003 (4)	0.001 (3)	−0.006 (4)
C23	0.027 (3)	0.034 (3)	0.046 (3)	0.002 (3)	0.006 (3)	0.000 (3)
C24	0.019 (3)	0.031 (3)	0.046 (3)	−0.001 (2)	0.007 (2)	0.004 (3)
C25	0.058 (5)	0.037 (4)	0.028 (3)	−0.010 (3)	0.010 (3)	−0.004 (3)
C26	0.062 (5)	0.032 (3)	0.030 (3)	0.001 (3)	0.018 (3)	−0.002 (3)
C27	0.039 (4)	0.038 (4)	0.035 (3)	0.002 (3)	0.012 (3)	0.006 (3)
C28	0.057 (5)	0.041 (4)	0.030 (3)	−0.007 (3)	0.018 (3)	−0.002 (3)
C29	0.068 (5)	0.029 (3)	0.032 (3)	0.004 (3)	0.024 (3)	0.005 (3)
C30	0.047 (4)	0.047 (4)	0.036 (3)	0.005 (3)	0.014 (3)	0.002 (3)
C31	0.057 (5)	0.041 (4)	0.048 (4)	0.011 (4)	0.023 (3)	0.008 (3)
N1	0.036 (3)	0.031 (3)	0.033 (2)	0.005 (2)	0.008 (2)	0.001 (2)
N2	0.033 (3)	0.037 (3)	0.044 (3)	−0.001 (2)	0.006 (2)	−0.002 (2)
N3	0.040 (3)	0.029 (3)	0.051 (3)	0.001 (2)	0.004 (2)	−0.003 (2)
N4	0.035 (3)	0.043 (3)	0.041 (3)	0.003 (2)	0.004 (2)	0.006 (2)
N5	0.057 (4)	0.072 (5)	0.044 (3)	−0.015 (4)	0.003 (3)	−0.009 (3)
N6	0.090 (5)	0.039 (4)	0.044 (3)	0.004 (3)	0.033 (3)	0.004 (3)
O1	0.083 (4)	0.104 (4)	0.088 (4)	0.034 (4)	0.022 (3)	0.021 (3)
O2	0.095 (5)	0.085 (4)	0.115 (5)	0.014 (4)	0.002 (4)	−0.007 (4)
O3	0.066 (3)	0.071 (3)	0.065 (3)	0.002 (3)	0.004 (3)	0.026 (3)
O4	0.101 (4)	0.040 (3)	0.095 (4)	0.019 (3)	0.007 (3)	0.017 (3)
O5	0.052 (4)	0.100 (4)	0.111 (4)	−0.002 (3)	0.006 (3)	−0.031 (3)
O6	0.091 (4)	0.051 (3)	0.090 (4)	−0.024 (3)	−0.015 (3)	0.003 (3)
O7	0.088 (4)	0.042 (3)	0.057 (3)	−0.005 (2)	0.021 (3)	−0.002 (2)
O8	0.069 (4)	0.060 (3)	0.072 (3)	0.017 (3)	0.022 (3)	0.009 (2)
O9	0.042 (3)	0.084 (4)	0.066 (3)	0.006 (3)	0.012 (2)	−0.002 (3)
O10	0.107 (5)	0.039 (3)	0.067 (3)	−0.016 (3)	0.025 (3)	−0.001 (2)
O11	0.089 (4)	0.042 (3)	0.081 (3)	0.016 (3)	0.036 (3)	0.022 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.404 (4)	C16—C24	1.392 (7)
Ag1—N2	2.348 (5)	C17—C18	1.476 (9)
Ag1—N3	2.335 (4)	C17—O3	1.220 (8)
Ag1—N4	2.376 (5)	C18—C19	1.498 (8)
C1—H1	0.93	C18—O4	1.227 (8)
C1—C2	1.376 (8)	C19—C20	1.386 (8)
C1—N1	1.334 (7)	C19—C23	1.400 (8)
C2—H2	0.93	C20—H20	0.93
C2—C3	1.373 (8)	C20—C21	1.359 (9)
C3—H3	0.93	C21—H21	0.93
C3—C4	1.372 (8)	C21—C22	1.373 (9)
C4—C5	1.475 (10)	C22—H22	0.93
C4—C12	1.402 (8)	C22—N4	1.341 (8)
C5—C6	1.349 (12)	C23—C24	1.478 (7)
C5—O1	1.298 (10)	C23—N4	1.349 (7)
C6—C7	1.493 (13)	C24—N3	1.344 (7)
C6—O2	1.283 (10)	C25—C26	1.430 (9)
C7—C8	1.399 (9)	C25—C30	1.384 (8)
C7—C11	1.385 (8)	C25—N5	1.450 (9)
C8—H8	0.93	C26—C27	1.418 (8)
C8—C9	1.357 (10)	C26—O7	1.293 (7)
C9—H9	0.93	C27—C28	1.373 (8)
C9—C10	1.353 (9)	C27—C31	1.496 (8)
C10—H10	0.93	C28—H28	0.93
C10—N2	1.347 (8)	C28—C29	1.407 (8)
C11—C12	1.481 (7)	C29—C30	1.380 (8)
C11—N2	1.326 (7)	C29—N6	1.458 (8)
C12—N1	1.344 (7)	C30—H30	0.93
C13—H13	0.93	C31—O8	1.286 (8)
C13—C14	1.381 (9)	C31—O9	1.223 (8)
C13—N3	1.339 (8)	N5—O5	1.230 (9)
C14—H14	0.93	N5—O6	1.218 (8)
C14—C15	1.373 (9)	N6—O10	1.216 (8)
C15—H15	0.93	N6—O11	1.257 (8)
C15—C16	1.396 (8)	O7—H7	1.346 (4)
C16—C17	1.473 (8)	O8—H7	1.155 (4)

H1—C1—C2	118.04	C19—C18—O4	120.9 (6)
H1—C1—N1	118.04	C18—C19—C20	121.6 (5)
C2—C1—N1	123.9 (5)	C18—C19—C23	119.3 (5)
C1—C2—H2	120.88	C20—C19—C23	119.1 (5)
C1—C2—C3	118.2 (5)	C19—C20—H20	119.84
H2—C2—C3	120.88	C19—C20—C21	120.3 (6)
C2—C3—H3	120.34	H20—C20—C21	119.84
C2—C3—C4	119.3 (5)	C20—C21—H21	121.42
H3—C3—C4	120.34	C20—C21—C22	117.2 (6)
C3—C4—C5	121.7 (6)	H21—C21—C22	121.42
C3—C4—C12	119.3 (5)	C21—C22—H22	117.46
C5—C4—C12	119.0 (5)	C21—C22—N4	125.1 (5)
C4—C5—C6	121.9 (8)	H22—C22—N4	117.46
C4—C5—O1	118.9 (7)	C19—C23—C24	121.2 (5)
C6—C5—O1	119.2 (8)	C19—C23—N4	120.8 (5)
C5—C6—C7	119.3 (7)	C24—C23—N4	118.0 (5)
C5—C6—O2	121.4 (9)	C16—C24—C23	120.2 (5)
C7—C6—O2	119.3 (7)	C16—C24—N3	122.5 (5)
C6—C7—C8	119.6 (6)	C23—C24—N3	117.2 (4)
C6—C7—C11	120.4 (6)	C26—C25—C30	121.2 (5)
C8—C7—C11	120.0 (6)	C26—C25—N5	122.7 (5)
C7—C8—H8	121.23	C30—C25—N5	116.1 (6)
C7—C8—C9	117.5 (6)	C25—C26—C27	117.1 (5)
H8—C8—C9	121.23	C25—C26—O7	122.2 (5)
C8—C9—H9	120.26	C27—C26—O7	120.5 (5)
C8—C9—C10	119.5 (6)	C26—C27—C28	122.1 (5)
H9—C9—C10	120.26	C26—C27—C31	120.1 (5)
C9—C10—H10	118.01	C28—C27—C31	117.8 (5)
C9—C10—N2	124.0 (6)	C27—C28—H28	121
H10—C10—N2	118.01	C27—C28—C29	118.0 (5)
C7—C11—C12	119.5 (5)	H28—C28—C29	121
C7—C11—N2	121.3 (5)	C28—C29—C30	122.6 (5)
C12—C11—N2	119.2 (5)	C28—C29—N6	118.3 (5)
C4—C12—C11	119.8 (5)	C30—C29—N6	119.1 (5)
C4—C12—N1	121.2 (5)	C25—C30—C29	118.7 (5)
C11—C12—N1	118.9 (5)	C25—C30—H30	120.65
H13—C13—C14	117.83	C29—C30—H30	120.65
H13—C13—N3	117.83	C27—C31—O8	116.2 (5)
C14—C13—N3	124.3 (5)	C27—C31—O9	120.8 (6)
C13—C14—H14	121.04	O8—C31—O9	122.9 (6)
C13—C14—C15	117.9 (6)	C1—N1—C12	117.9 (4)
H14—C14—C15	121.04	C10—N2—C11	117.6 (5)
C14—C15—H15	120.29	C13—N3—C24	117.3 (5)
C14—C15—C16	119.4 (5)	C22—N4—C23	117.5 (5)
H15—C15—C16	120.29	C25—N5—O5	118.4 (6)
C15—C16—C17	120.1 (5)	C25—N5—O6	120.0 (6)
C15—C16—C24	118.5 (5)	O5—N5—O6	121.6 (6)
C17—C16—C24	121.4 (5)	C29—N6—O10	118.3 (5)
C16—C17—C18	118.1 (5)	C29—N6—O11	117.2 (5)
C16—C17—O3	122.0 (6)	O10—N6—O11	124.5 (5)
C18—C17—O3	119.9 (6)	C26—O7—H7	99.4 (4)
C17—C18—C19	119.0 (5)	C31—O8—H7	103.7 (4)
C17—C18—O4	120.1 (6)	O7—H7—O8	159.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O10ⁱ	0.93	2.49	3.180 (7)	131
C8—H8···O7ⁱⁱ	0.93	2.32	3.220 (7)	162
C9—H9···O6ⁱⁱ	0.93	2.49	3.243 (9)	138
C13—H13···O4ⁱⁱⁱ	0.93	2.47	3.209 (7)	137
C22—H22···O8	0.93	2.36	3.251 (7)	160
O7—H7···C31	1.346 (4)	1.922 (7)	2.833 (8)	119.1 (3)
O7—H7···O8	1.346 (4)	1.155 (4)	2.462 (6)	159.6 (3)
O8—H7···C26	1.155 (4)	2.013 (6)	2.781 (7)	120.3 (3)
O8—H7···O7	1.155 (4)	1.346 (4)	2.462 (6)	159.6 (3)

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

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET) top

Crystal data top

C₅H₉N₂⁺·C₇H₃N₂O₇⁻	F(000) = 336
M_r = 324.26	D_x = 1.547 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.1183 (7) Å	Cell parameters from 1025 reflections
b = 6.0636 (5) Å	θ = 2.5–22.6°
c = 14.1453 (11) Å	µ = 0.13 mm⁻¹
β = 91.904 (1)°	T = 293 K
V = 695.93 (10) Å³	Block, colorless
Z = 2	0.40 × 0.27 × 0.11 mm

Data collection top

Bruker SMART CCD diffractometer	2301 independent reflections
Radiation source: fine-focus sealed tube	1444 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
T_min = 0.959, T_max = 0.986	k = −7→7
3523 measured reflections	l = −16→12

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.041	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
wR(F) = 0.088	(Δ/σ)_max = 0.033
S = 1.16	Δρ_max = 0.11 e Å⁻³
2301 reflections	Δρ_min = −0.10 e Å⁻³
212 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 3100 (400)
37 constraints	Absolute structure: 955 of Friedel pairs used in the refinement
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.5
Secondary atom site location: difference Fourier map

Special details top

Number of fixed parameters 10.

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

	x	y	z	U_iso*/U_eq
N1	0.2262 (4)	0.7164 (5)	0.2338 (2)	0.0464 (11)
N2	0.2203 (3)	0.6196 (5)	0.3198 (2)	0.0478 (11)
C6	0.3519 (4)	0.7226 (6)	0.5525 (2)	0.0412 (12)
N3	0.2179 (3)	1.3158 (5)	0.7705 (2)	0.0509 (12)
N4	0.5552 (4)	0.7120 (5)	0.8913 (2)	0.0501 (12)
O1	0.5417 (3)	0.5285 (4)	0.70239 (16)	0.0462 (9)
O2	0.4266 (3)	0.5357 (4)	0.53811 (15)	0.0582 (10)
O3	0.2657 (3)	0.8100 (4)	0.49006 (14)	0.0507 (8)
O4	0.1415 (3)	1.4013 (4)	0.70419 (18)	0.0652 (10)
O5	0.2270 (3)	1.3968 (4)	0.85025 (18)	0.0709 (11)
O6	0.5263 (4)	0.7839 (5)	0.96960 (17)	0.0853 (12)
O7	0.6549 (4)	0.5664 (5)	0.87980 (17)	0.0719 (12)
C1	0.1300 (5)	0.6431 (8)	0.0685 (2)	0.0762 (19)
H1a	0.132119	0.800298	0.060733	0.1144*
H1b	0.027525	0.586015	0.043068	0.1144*
H1c	0.219699	0.578396	0.035744	0.1144*
C2	0.1466 (4)	0.5878 (6)	0.1713 (2)	0.0469 (13)
C3	0.0892 (4)	0.4058 (7)	0.2187 (3)	0.0553 (14)
H3	0.029651	0.288588	0.192446	0.0663*
C4	0.1373 (4)	0.4313 (6)	0.3133 (2)	0.0481 (13)
C5	0.1093 (5)	0.2896 (7)	0.3966 (3)	0.0669 (16)
H5a	0.025142	0.183251	0.380914	0.1003*
H5b	0.20964	0.214551	0.414477	0.1003*
H5c	0.074882	0.379302	0.448238	0.1003*
C12	0.4691 (4)	0.7102 (6)	0.7196 (2)	0.0372 (12)
C7	0.3736 (3)	0.8233 (6)	0.6477 (2)	0.0348 (11)
C8	0.2972 (4)	1.0181 (6)	0.6641 (2)	0.0380 (12)
H8	0.239805	1.089516	0.615013	0.0456*
C9	0.3044 (4)	1.1108 (6)	0.7534 (2)	0.0381 (11)
C10	0.3902 (4)	1.0091 (6)	0.8274 (2)	0.0403 (12)
H10	0.393751	1.071121	0.887603	0.0483*
C11	0.4704 (4)	0.8133 (6)	0.8100 (2)	0.0380 (11)
H2a	0.507 (5)	0.485 (9)	0.620 (3)	0.145 (19)*
H1	0.289 (6)	0.878 (9)	0.225 (3)	0.130 (19)*
H2	0.258 (4)	0.707 (6)	0.373 (2)	0.063 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0502 (18)	0.049 (2)	0.0399 (18)	0.0006 (15)	−0.0027 (14)	−0.0034 (15)
N2	0.0497 (19)	0.051 (2)	0.0422 (18)	−0.0046 (17)	−0.0047 (14)	−0.0066 (17)
C6	0.0393 (19)	0.047 (2)	0.037 (2)	−0.0016 (18)	0.0053 (16)	−0.0027 (18)
N3	0.0500 (19)	0.043 (2)	0.060 (2)	−0.0003 (17)	0.0048 (16)	−0.0031 (18)
N4	0.065 (2)	0.046 (2)	0.0387 (19)	0.0015 (17)	−0.0037 (16)	0.0042 (16)
O1	0.0564 (15)	0.0414 (15)	0.0407 (14)	0.0091 (13)	−0.0027 (11)	−0.0072 (12)
O2	0.0704 (17)	0.0626 (18)	0.0414 (14)	0.0205 (15)	−0.0036 (12)	−0.0156 (14)
O3	0.0581 (14)	0.0600 (17)	0.0333 (13)	0.0050 (14)	−0.0083 (11)	0.0013 (12)
O4	0.0703 (17)	0.0521 (17)	0.0721 (18)	0.0185 (15)	−0.0141 (14)	0.0031 (15)
O5	0.092 (2)	0.0593 (19)	0.0617 (17)	0.0072 (16)	0.0048 (14)	−0.0187 (15)
O6	0.148 (3)	0.075 (2)	0.0326 (16)	0.035 (2)	−0.0069 (15)	−0.0032 (15)
O7	0.092 (2)	0.072 (2)	0.0510 (16)	0.0308 (19)	−0.0083 (14)	0.0090 (16)
C1	0.086 (3)	0.096 (4)	0.047 (2)	−0.014 (3)	−0.009 (2)	−0.007 (2)
C2	0.043 (2)	0.054 (3)	0.0434 (19)	0.005 (2)	−0.0046 (17)	−0.009 (2)
C3	0.049 (2)	0.057 (3)	0.060 (2)	−0.004 (2)	−0.0075 (18)	−0.022 (2)
C4	0.039 (2)	0.044 (2)	0.062 (2)	0.0027 (19)	0.0037 (17)	−0.003 (2)
C5	0.066 (3)	0.060 (3)	0.074 (3)	0.000 (2)	−0.002 (2)	0.012 (2)
C12	0.0351 (19)	0.041 (2)	0.036 (2)	−0.0079 (18)	0.0025 (15)	0.0010 (17)
C7	0.0342 (17)	0.039 (2)	0.0316 (17)	−0.0052 (17)	0.0004 (13)	0.0031 (16)
C8	0.041 (2)	0.038 (2)	0.0349 (19)	−0.0032 (18)	−0.0036 (15)	0.0039 (17)
C9	0.041 (2)	0.032 (2)	0.0416 (19)	−0.0045 (17)	0.0020 (15)	−0.0015 (17)
C10	0.049 (2)	0.039 (2)	0.0325 (19)	−0.0038 (18)	0.0020 (16)	−0.0017 (17)
C11	0.0419 (19)	0.041 (2)	0.0312 (17)	−0.0038 (19)	−0.0025 (14)	0.0049 (17)

Geometric parameters (Å, º) top

N1—N2	1.353 (4)	H1a—H1b	1.5677
N1—C2	1.330 (5)	H1a—H1c	1.5677
N1—H1	1.11 (5)	H1b—H1c	1.5677
N2—C4	1.327 (5)	C2—C3	1.380 (5)
N2—H2	0.96 (3)	C3—H3	0.93
C6—O2	1.304 (4)	C3—C4	1.389 (5)
C6—O3	1.229 (4)	C4—C5	1.482 (5)
C6—C7	1.484 (4)	C5—H5a	0.96
N3—O4	1.223 (4)	C5—H5b	0.96
N3—O5	1.231 (4)	C5—H5c	0.96
N3—C9	1.452 (5)	H5a—H5b	1.5677
N4—O6	1.220 (4)	H5a—H5c	1.5677
N4—O7	1.213 (4)	H5b—H5c	1.5677
N4—C11	1.457 (4)	C12—C7	1.433 (4)
O1—C12	1.277 (4)	C12—C11	1.422 (4)
O1—H2a	1.22 (5)	C7—C8	1.358 (5)
O2—H2a	1.34 (5)	C8—H8	0.93
C1—H1a	0.96	C8—C9	1.382 (4)
C1—H1b	0.96	C9—C10	1.384 (4)
C1—H1c	0.96	C10—H10	0.93
C1—C2	1.494 (5)	C10—C11	1.380 (5)

N2—N1—C2	108.2 (3)	N2—C4—C3	106.8 (3)
N2—N1—H1	121 (2)	N2—C4—C5	122.3 (3)
C2—N1—H1	131 (2)	C3—C4—C5	130.9 (3)
N1—N2—C4	110.1 (3)	C4—C5—H5a	109.47
N1—N2—H2	117 (2)	C4—C5—H5b	109.47
C4—N2—H2	132 (2)	C4—C5—H5c	109.47
O2—C6—O3	121.3 (3)	H5a—C5—H5b	109.47
O2—C6—C7	117.2 (3)	H5a—C5—H5c	109.47
O3—C6—C7	121.5 (3)	H5b—C5—H5c	109.47
O4—N3—O5	123.2 (3)	O1—C12—C7	121.3 (3)
O4—N3—C9	118.1 (3)	O1—C12—C11	124.1 (3)
O5—N3—C9	118.7 (3)	C7—C12—C11	114.5 (3)
O6—N4—O7	122.1 (3)	C6—C7—C12	119.5 (3)
O6—N4—C11	117.8 (3)	C6—C7—C8	118.1 (3)
O7—N4—C11	120.1 (3)	C12—C7—C8	122.3 (3)
C12—O1—H2a	106 (2)	C7—C8—H8	119.87
C6—O2—H2a	106 (2)	C7—C8—C9	120.3 (3)
H1a—C1—H1b	109.47	H8—C8—C9	119.87
H1a—C1—H1c	109.47	N3—C9—C8	119.6 (3)
H1a—C1—C2	109.47	N3—C9—C10	119.3 (3)
H1b—C1—H1c	109.47	C8—C9—C10	121.0 (3)
H1b—C1—C2	109.47	C9—C10—H10	120.77
H1c—C1—C2	109.47	C9—C10—C11	118.5 (3)
N1—C2—C1	122.8 (3)	H10—C10—C11	120.77
N1—C2—C3	108.1 (3)	N4—C11—C12	120.9 (3)
C1—C2—C3	129.1 (3)	N4—C11—C10	115.7 (3)
C2—C3—H3	126.58	C12—C11—C10	123.3 (3)
C2—C3—C4	106.8 (3)	O1—H2a—O2	149 (5)
H3—C3—C4	126.58

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1a···O7ⁱ	0.96	2.49	3.176 (5)	128
C5—H5a···O4ⁱⁱ	0.96	2.47	3.395 (5)	162
C10—H10···O6ⁱⁱⁱ	0.93	2.47	3.369 (4)	164
O1—H2a···O2	1.22 (5)	1.34 (5)	2.476 (3)	149 (5)
O2—H2a···O1	1.34 (5)	1.22 (5)	2.476 (3)	149 (5)
N1—H1···O1ⁱ	1.11 (5)	1.92 (5)	2.799 (4)	133 (3)
N1—H1···O7ⁱ	1.11 (5)	1.94 (5)	2.850 (4)	137 (3)
N2—H2···O3	0.96 (3)	1.77 (3)	2.685 (4)	158 (3)

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

3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) top

Crystal data top

C₆H₁₂N₃⁺·C₇H₃N₂O₇⁻	Z = 2
M_r = 353.30	F(000) = 368
Triclinic, P1	D_x = 1.525 Mg m⁻³
a = 7.0109 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.6617 (8) Å	Cell parameters from 2218 reflections
c = 10.7454 (7) Å	θ = 4.2–72.3°
α = 93.075 (6)°	µ = 1.09 mm⁻¹
β = 95.863 (5)°	T = 173 K
γ = 104.944 (6)°	Irregular, yellow
V = 769.30 (9) Å³	0.22 × 0.14 × 0.12 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	2953 independent reflections
Graphite monochromator	2426 reflections with I > 3σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.026
ω scans	θ_max = 72.5°, θ_min = 4.2°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −8→5
T_min = 0.925, T_max = 1.000	k = −12→13
4664 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F > 3σ(F)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F) = 0.100	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.64	(Δ/σ)_max = 0.013
2953 reflections	Δρ_max = 0.21 e Å⁻³
229 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
46 constraints	Extinction coefficient: 740 (130)

Special details top

Refinement. Number of fixed parameters: 12

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

	x	y	z	U_iso*/U_eq
O1b	−0.19161 (17)	0.67539 (12)	0.52684 (11)	0.0294 (4)
O2b	−0.38292 (17)	0.47166 (12)	0.40838 (12)	0.0313 (4)
O3b	−0.25511 (17)	0.37712 (12)	0.26158 (12)	0.0312 (4)
O4b	0.41258 (19)	0.58639 (13)	0.16853 (13)	0.0365 (5)
O5b	0.59776 (18)	0.75622 (13)	0.28239 (14)	0.0382 (5)
O6b	0.3446 (2)	0.93719 (14)	0.62658 (15)	0.0474 (5)
O7b	0.02822 (19)	0.91655 (13)	0.61477 (13)	0.0410 (5)
N1b	0.1720 (2)	0.88469 (14)	0.58118 (14)	0.0301 (5)
N2b	0.4396 (2)	0.67347 (14)	0.25363 (14)	0.0281 (5)
C1b	−0.0455 (2)	0.68023 (16)	0.46268 (15)	0.0225 (5)
C2b	−0.0572 (2)	0.57873 (15)	0.36597 (15)	0.0217 (5)
C3b	0.0987 (2)	0.57933 (16)	0.29810 (15)	0.0228 (5)
H3b	0.086172	0.512562	0.233219	0.0273*
C4b	0.2738 (2)	0.67709 (16)	0.32422 (15)	0.0238 (5)
C5b	0.2967 (2)	0.77664 (16)	0.41630 (15)	0.0244 (5)
H5b	0.418494	0.842618	0.433677	0.0292*
C6b	0.1392 (2)	0.77850 (16)	0.48267 (15)	0.0244 (5)
C7b	−0.2405 (2)	0.46767 (16)	0.33986 (15)	0.0245 (5)
N1a	−0.2235 (2)	0.05127 (14)	−0.17301 (14)	0.0305 (5)
N2a	−0.0146 (2)	0.22579 (13)	−0.06967 (13)	0.0239 (4)
N3a	0.3467 (2)	0.20531 (13)	0.28160 (13)	0.0254 (4)
C1a	−0.0395 (2)	0.12591 (16)	−0.15749 (16)	0.0272 (6)
H1a	0.06324	0.111094	−0.202772	0.0327*
C2a	−0.3211 (3)	0.10665 (17)	−0.08987 (17)	0.0314 (6)
H2a	−0.457443	0.07432	−0.079116	0.0377*
C3a	−0.1954 (3)	0.21356 (17)	−0.02572 (17)	0.0294 (6)
H3a	−0.225845	0.269084	0.03706	0.0353*
C4a	0.1719 (2)	0.32466 (17)	−0.02832 (15)	0.0268 (5)
H4aa	0.242014	0.351332	−0.101965	0.0322*
H4ab	0.142708	0.403798	0.008481	0.0322*
C5a	0.3076 (2)	0.27759 (16)	0.06668 (16)	0.0271 (5)
H5aa	0.324487	0.193134	0.033664	0.0326*
H5ab	0.440667	0.340434	0.079114	0.0326*
C6a	0.2253 (2)	0.26206 (16)	0.19085 (15)	0.0279 (6)
H6aa	0.218227	0.347891	0.227027	0.0335*
H6ab	0.08712	0.206021	0.17726	0.0335*
H2b	−0.339134	0.554144	0.46148	0.075 (9)*
H3aa	0.329781	0.119532	0.260701	0.045 (4)*
H3ab	0.475827	0.248704	0.284554	0.045 (4)*
H3ac	0.313145	0.21209	0.359189	0.045 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1b	0.0268 (6)	0.0307 (7)	0.0277 (6)	0.0010 (5)	0.0098 (5)	−0.0050 (5)
O2b	0.0247 (6)	0.0313 (7)	0.0327 (7)	−0.0024 (5)	0.0088 (5)	−0.0060 (5)
O3b	0.0283 (6)	0.0285 (7)	0.0317 (7)	0.0002 (5)	0.0047 (5)	−0.0082 (5)
O4b	0.0371 (7)	0.0325 (7)	0.0413 (8)	0.0085 (6)	0.0167 (6)	−0.0042 (6)
O5b	0.0231 (6)	0.0380 (8)	0.0506 (9)	0.0010 (6)	0.0111 (6)	0.0014 (6)
O6b	0.0352 (7)	0.0408 (8)	0.0552 (10)	−0.0009 (6)	−0.0052 (7)	−0.0197 (7)
O7b	0.0398 (7)	0.0333 (7)	0.0470 (8)	0.0034 (6)	0.0162 (6)	−0.0121 (6)
N1b	0.0326 (8)	0.0241 (8)	0.0301 (8)	0.0012 (6)	0.0060 (6)	−0.0023 (6)
N2b	0.0260 (7)	0.0259 (7)	0.0343 (8)	0.0074 (6)	0.0092 (6)	0.0063 (6)
C1b	0.0234 (8)	0.0236 (8)	0.0201 (8)	0.0054 (6)	0.0034 (6)	0.0027 (6)
C2b	0.0218 (8)	0.0215 (8)	0.0207 (8)	0.0036 (6)	0.0019 (6)	0.0029 (6)
C3b	0.0265 (8)	0.0220 (8)	0.0208 (8)	0.0077 (7)	0.0043 (6)	0.0017 (6)
C4b	0.0220 (8)	0.0254 (8)	0.0260 (8)	0.0080 (7)	0.0064 (7)	0.0057 (7)
C5b	0.0220 (8)	0.0220 (8)	0.0269 (8)	0.0015 (6)	0.0023 (7)	0.0050 (7)
C6b	0.0276 (8)	0.0210 (8)	0.0230 (8)	0.0045 (7)	0.0018 (7)	−0.0001 (6)
C7b	0.0247 (8)	0.0261 (8)	0.0216 (8)	0.0051 (7)	0.0021 (6)	0.0007 (6)
N1a	0.0292 (8)	0.0252 (8)	0.0349 (8)	0.0050 (6)	0.0011 (6)	−0.0007 (6)
N2a	0.0247 (7)	0.0234 (7)	0.0229 (7)	0.0054 (6)	0.0034 (5)	0.0002 (6)
N3a	0.0268 (7)	0.0229 (7)	0.0245 (7)	0.0041 (6)	0.0021 (6)	−0.0026 (6)
C1a	0.0286 (9)	0.0260 (9)	0.0278 (9)	0.0087 (7)	0.0051 (7)	−0.0018 (7)
C2a	0.0269 (9)	0.0316 (10)	0.0352 (10)	0.0047 (7)	0.0073 (7)	0.0060 (8)
C3a	0.0301 (9)	0.0311 (9)	0.0289 (9)	0.0095 (7)	0.0092 (7)	0.0016 (7)
C4a	0.0277 (8)	0.0248 (8)	0.0248 (8)	0.0009 (7)	0.0052 (7)	0.0000 (7)
C5a	0.0237 (8)	0.0295 (9)	0.0260 (9)	0.0030 (7)	0.0055 (7)	−0.0021 (7)
C6a	0.0301 (9)	0.0306 (9)	0.0261 (9)	0.0125 (7)	0.0053 (7)	0.0016 (7)

Geometric parameters (Å, º) top

O1b—C1b	1.284 (2)	N1a—C2a	1.376 (3)
O2b—C7b	1.308 (2)	N2a—C1a	1.348 (2)
O2b—H2b	0.9820 (12)	N2a—C3a	1.375 (2)
O3b—C7b	1.222 (2)	N2a—C4a	1.4622 (19)
O4b—N2b	1.232 (2)	N3a—C6a	1.483 (2)
O5b—N2b	1.2248 (17)	N3a—H3aa	0.9042 (14)
O6b—N1b	1.2313 (18)	N3a—H3ab	0.9009 (13)
O7b—N1b	1.225 (2)	N3a—H3ac	0.8932 (14)
N1b—C6b	1.464 (2)	C1a—H1a	0.95
N2b—C4b	1.458 (2)	C2a—H2a	0.95
C1b—C2b	1.440 (2)	C2a—C3a	1.351 (2)
C1b—C6b	1.428 (2)	C3a—H3a	0.95
C2b—C3b	1.373 (2)	C4a—H4aa	0.99
C2b—C7b	1.496 (2)	C4a—H4ab	0.99
C3b—H3b	0.95	C4a—C5a	1.517 (2)
C3b—C4b	1.382 (2)	C5a—H5aa	0.99
C4b—C5b	1.378 (2)	C5a—H5ab	0.99
C5b—H5b	0.95	C5a—C6a	1.507 (2)
C5b—C6b	1.378 (2)	C6a—H6aa	0.99
N1a—C1a	1.318 (2)	C6a—H6ab	0.99

C1b—O1b—H2b	99.82 (10)	C6a—N3a—H3ab	109.46 (13)
C7b—O2b—H2b	106.90 (11)	C6a—N3a—H3ac	111.76 (15)
O6b—N1b—O7b	123.30 (15)	H3aa—N3a—H3ab	110.21 (16)
O6b—N1b—C6b	117.72 (16)	H3aa—N3a—H3ac	106.71 (14)
O7b—N1b—C6b	118.97 (13)	H3ab—N3a—H3ac	107.27 (13)
O4b—N2b—O5b	123.59 (16)	N1a—C1a—N2a	111.91 (16)
O4b—N2b—C4b	117.89 (12)	N1a—C1a—H1a	124.04
O5b—N2b—C4b	118.52 (14)	N2a—C1a—H1a	124.04
O1b—C1b—C2b	120.19 (13)	N1a—C2a—H2a	124.86
O1b—C1b—C6b	124.76 (15)	N1a—C2a—C3a	110.28 (15)
C2b—C1b—C6b	115.00 (15)	H2a—C2a—C3a	124.86
C1b—C2b—C3b	121.54 (13)	N2a—C3a—C2a	106.10 (16)
C1b—C2b—C7b	119.88 (15)	N2a—C3a—H3a	126.95
C3b—C2b—C7b	118.56 (14)	C2a—C3a—H3a	126.95
C2b—C3b—H3b	120.01	N2a—C4a—H4aa	109.47
C2b—C3b—C4b	119.99 (15)	N2a—C4a—H4ab	109.47
H3b—C3b—C4b	120.01	N2a—C4a—C5a	112.62 (14)
N2b—C4b—C3b	119.03 (14)	H4aa—C4a—H4ab	106.12
N2b—C4b—C5b	119.24 (13)	H4aa—C4a—C5a	109.47
C3b—C4b—C5b	121.73 (16)	H4ab—C4a—C5a	109.47
C4b—C5b—H5b	120.69	C4a—C5a—H5aa	109.47
C4b—C5b—C6b	118.62 (13)	C4a—C5a—H5ab	109.47
H5b—C5b—C6b	120.69	C4a—C5a—C6a	111.50 (15)
N1b—C6b—C1b	120.26 (15)	H5aa—C5a—H5ab	107.36
N1b—C6b—C5b	116.59 (13)	H5aa—C5a—C6a	109.47
C1b—C6b—C5b	123.09 (15)	H5ab—C5a—C6a	109.47
O2b—C7b—O3b	121.86 (14)	N3a—C6a—C5a	112.35 (15)
O2b—C7b—C2b	115.78 (14)	N3a—C6a—H6aa	109.47
O3b—C7b—C2b	122.33 (16)	N3a—C6a—H6ab	109.47
C1a—N1a—C2a	105.01 (14)	C5a—C6a—H6aa	109.47
C1a—N2a—C3a	106.69 (13)	C5a—C6a—H6ab	109.47
C1a—N2a—C4a	125.73 (15)	H6aa—C6a—H6ab	106.43
C3a—N2a—C4a	127.56 (14)	O1b—H2b—O2b	156.29 (9)
C6a—N3a—H3aa	111.33 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4a—H4aa···O4bⁱ	0.99	2.53	3.359 (2)	141
O2b—H2b···O1b	0.9820 (12)	1.5161 (11)	2.4473 (16)	156.29 (9)
O2b—H2b···C1b	0.9820 (12)	2.1471 (15)	2.7833 (18)	121.00 (8)
N3a—H3aa···N1aⁱⁱ	0.9042 (14)	1.9318 (14)	2.797 (2)	159.6 (1)
N3a—H3ab···O2bⁱⁱⁱ	0.9009 (13)	2.5650 (12)	3.1297 (17)	121.35 (10)
N3a—H3ab···O3bⁱⁱⁱ	0.9009 (13)	2.0721 (11)	2.9537 (17)	165.79 (10)
N3a—H3ac···O1b^iv	0.8932 (14)	2.0610 (13)	2.815 (2)	141.47 (11)
N3a—H3ac···O7b^iv	0.8932 (14)	2.4844 (13)	2.9712 (19)	114.74 (8)

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

4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV) top

Crystal data top

C₁₀H₁₂N₃O₃S⁺·C₇H₃N₂O₇⁻	Z = 2
M_r = 481.41	F(000) = 496
Triclinic, P1	D_x = 1.609 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5551 (1) Å	Cell parameters from 6718 reflections
b = 10.5000 (2) Å	θ = 1.8–32.6°
c = 12.7576 (3) Å	µ = 0.23 mm⁻¹
α = 106.463 (1)°	T = 296 K
β = 100.913 (1)°	Prism, yellow
γ = 108.272 (1)°	0.20 × 0.20 × 0.16 mm
V = 993.72 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	6717 independent reflections
Radiation source: fine-focus sealed tube	4398 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.030
ω and φ scan	θ_max = 32.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.955, T_max = 0.964	k = −15→15
24261 measured reflections	l = −19→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.044	Hydrogen site location: difference Fourier map
wR(F) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.95	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
6717 reflections	(Δ/σ)_max = 0.013
301 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³
48 constraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Number of fixed parameters: 9

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

	x	y	z	U_iso*/U_eq
S1	−0.02012 (4)	0.65156 (4)	0.38514 (3)	0.03475 (15)
O1	−0.12136 (12)	0.56298 (10)	0.26952 (9)	0.0472 (5)
O2	−0.09555 (13)	0.65440 (11)	0.47594 (9)	0.0468 (5)
O3	0.47434 (14)	0.55510 (13)	0.32058 (11)	0.0626 (6)
N1	0.29155 (15)	1.24477 (12)	0.38430 (11)	0.0434 (6)
N2	0.13845 (14)	0.60248 (12)	0.42019 (10)	0.0376 (5)
N3	0.39246 (16)	0.57705 (15)	0.40555 (12)	0.0536 (6)
C1	0.07464 (15)	0.82919 (13)	0.38935 (12)	0.0322 (5)
C2	0.21693 (19)	0.93183 (16)	0.47844 (13)	0.0511 (7)
C3	0.28732 (19)	1.06857 (16)	0.47796 (14)	0.0514 (7)
C4	0.21467 (16)	1.10142 (13)	0.38945 (12)	0.0344 (6)
C5	0.07052 (18)	1.00124 (15)	0.30229 (13)	0.0444 (7)
C6	0.00046 (17)	0.86380 (15)	0.30181 (13)	0.0421 (6)
C7	0.24788 (17)	0.58299 (13)	0.35471 (13)	0.0355 (6)
C8	0.2306 (2)	0.56568 (16)	0.23936 (14)	0.0473 (7)
C9	0.3761 (2)	0.55015 (16)	0.22381 (16)	0.0511 (8)
C10	0.4452 (3)	0.5287 (2)	0.12416 (18)	0.0766 (11)
O4	0.51685 (14)	0.76882 (14)	0.75724 (10)	0.0657 (6)
O5	0.25004 (13)	0.72390 (11)	0.65907 (9)	0.0495 (5)
O6	0.03442 (11)	0.74382 (11)	0.75483 (8)	0.0431 (4)
O7	−0.13539 (17)	0.8490 (2)	0.89544 (14)	0.0980 (10)
O8	−0.12065 (16)	0.7660 (2)	1.03000 (12)	0.0975 (9)
O9	0.46550 (16)	0.90412 (15)	1.25865 (10)	0.0717 (7)
O10	0.66293 (15)	0.90569 (15)	1.17611 (11)	0.0749 (7)
N4	−0.06158 (16)	0.80710 (17)	0.96062 (13)	0.0598 (7)
N5	0.51466 (16)	0.88865 (13)	1.17407 (12)	0.0488 (6)
C11	0.31789 (15)	0.78551 (13)	0.85956 (12)	0.0326 (5)
C12	0.14714 (16)	0.77857 (13)	0.85292 (12)	0.0328 (5)
C13	0.10840 (16)	0.80786 (15)	0.95755 (13)	0.0389 (6)
C14	0.22578 (17)	0.84024 (15)	1.06095 (13)	0.0403 (6)
C15	0.38931 (16)	0.84763 (14)	1.06263 (12)	0.0365 (6)
C16	0.43735 (16)	0.82163 (13)	0.96389 (12)	0.0356 (6)
C17	0.36856 (18)	0.75728 (15)	0.75210 (13)	0.0400 (6)
H1a	0.188848	1.256572	0.342213	0.088 (4)*
H1b	0.353568	1.297412	0.446823	0.088 (4)*
H1c	0.348288	1.238627	0.338232	0.088 (4)*
H2	0.265121	0.908789	0.538567	0.0613*
H2a	0.186499	0.630039	0.50234	0.068 (5)*
H3	0.383907	1.138439	0.537561	0.0617*
H5	0.020222	1.025766	0.243815	0.0533*
H6	−0.096798	0.794538	0.242417	0.0506*
H8	0.139615	0.565054	0.185878	0.0568*
H10a	0.551947	0.608597	0.142286	0.1149*
H10b	0.362955	0.522551	0.058321	0.1149*
H10c	0.46505	0.441064	0.1077	0.1149*
H14	0.194965	0.856742	1.128171	0.0484*
H16	0.549353	0.82833	0.967386	0.0428*
H6a	0.115577	0.727699	0.69023	0.132 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03683 (17)	0.03321 (18)	0.0360 (2)	0.01370 (13)	0.01260 (14)	0.01423 (16)
O1	0.0462 (5)	0.0373 (5)	0.0422 (7)	0.0089 (4)	0.0009 (5)	0.0087 (5)
O2	0.0524 (6)	0.0510 (6)	0.0532 (7)	0.0246 (5)	0.0309 (5)	0.0276 (6)
O3	0.0518 (6)	0.0718 (8)	0.0660 (9)	0.0313 (6)	0.0248 (6)	0.0153 (7)
N1	0.0510 (7)	0.0374 (6)	0.0502 (9)	0.0178 (5)	0.0268 (6)	0.0202 (6)
N2	0.0476 (6)	0.0413 (6)	0.0327 (7)	0.0235 (5)	0.0154 (5)	0.0169 (6)
N3	0.0495 (7)	0.0628 (9)	0.0487 (9)	0.0283 (6)	0.0154 (6)	0.0136 (7)
C1	0.0350 (6)	0.0317 (7)	0.0316 (8)	0.0143 (5)	0.0112 (5)	0.0120 (6)
C2	0.0588 (9)	0.0433 (9)	0.0382 (9)	0.0107 (7)	−0.0053 (7)	0.0197 (8)
C3	0.0520 (9)	0.0380 (8)	0.0432 (10)	0.0029 (7)	−0.0033 (7)	0.0129 (8)
C4	0.0400 (7)	0.0320 (7)	0.0393 (9)	0.0172 (6)	0.0208 (6)	0.0153 (6)
C5	0.0478 (8)	0.0446 (8)	0.0438 (10)	0.0195 (7)	0.0064 (7)	0.0235 (8)
C6	0.0392 (7)	0.0397 (8)	0.0403 (9)	0.0118 (6)	0.0004 (6)	0.0159 (7)
C7	0.0414 (7)	0.0275 (7)	0.0374 (9)	0.0132 (5)	0.0131 (6)	0.0113 (6)
C8	0.0553 (9)	0.0506 (9)	0.0426 (10)	0.0238 (7)	0.0203 (7)	0.0194 (8)
C9	0.0605 (9)	0.0379 (8)	0.0574 (12)	0.0169 (7)	0.0325 (9)	0.0141 (8)
C10	0.0921 (14)	0.0731 (13)	0.0819 (15)	0.0351 (12)	0.0607 (13)	0.0275 (13)
O4	0.0483 (6)	0.0981 (10)	0.0513 (8)	0.0274 (6)	0.0254 (5)	0.0227 (7)
O5	0.0578 (6)	0.0613 (7)	0.0295 (6)	0.0241 (5)	0.0132 (5)	0.0156 (5)
O6	0.0404 (5)	0.0525 (6)	0.0322 (6)	0.0196 (4)	0.0028 (4)	0.0136 (5)
O7	0.0700 (8)	0.1711 (16)	0.0831 (11)	0.0810 (10)	0.0212 (8)	0.0529 (11)
O8	0.0537 (7)	0.1721 (16)	0.0566 (9)	0.0299 (9)	0.0287 (7)	0.0359 (10)
O9	0.0770 (8)	0.0950 (10)	0.0308 (7)	0.0267 (7)	0.0041 (6)	0.0211 (7)
O10	0.0480 (7)	0.0991 (10)	0.0639 (9)	0.0302 (6)	−0.0064 (6)	0.0241 (8)
N4	0.0396 (7)	0.0856 (11)	0.0419 (9)	0.0249 (7)	0.0082 (6)	0.0084 (8)
N5	0.0478 (7)	0.0458 (7)	0.0405 (9)	0.0147 (6)	−0.0044 (6)	0.0138 (7)
C11	0.0346 (6)	0.0281 (6)	0.0318 (8)	0.0107 (5)	0.0078 (5)	0.0096 (6)
C12	0.0351 (6)	0.0301 (7)	0.0291 (8)	0.0112 (5)	0.0039 (5)	0.0104 (6)
C13	0.0330 (6)	0.0444 (8)	0.0356 (9)	0.0154 (6)	0.0079 (6)	0.0108 (7)
C14	0.0424 (7)	0.0454 (8)	0.0301 (8)	0.0162 (6)	0.0100 (6)	0.0112 (7)
C15	0.0370 (7)	0.0341 (7)	0.0297 (8)	0.0107 (5)	−0.0009 (6)	0.0104 (6)
C16	0.0321 (6)	0.0324 (7)	0.0393 (9)	0.0124 (5)	0.0061 (6)	0.0120 (6)
C17	0.0411 (7)	0.0393 (8)	0.0385 (9)	0.0139 (6)	0.0130 (6)	0.0143 (7)

Geometric parameters (Å, º) top

S1—O1	1.4228 (9)	C9—C10	1.491 (3)
S1—O2	1.4264 (13)	C10—H10a	0.96
S1—N2	1.6264 (14)	C10—H10b	0.96
O3—N3	1.402 (2)	C10—H10c	0.96
O3—C9	1.333 (2)	O4—C17	1.223 (2)
N1—C4	1.468 (2)	O5—C17	1.2827 (18)
N1—H1a	1.0015 (14)	O5—H6a	1.2945 (12)
N1—H1b	0.7932 (11)	O6—C12	1.3010 (16)
N1—H1c	0.8315 (15)	O6—H6a	1.1837 (11)
N2—C7	1.391 (2)	O7—N4	1.211 (3)
N2—H2a	0.9703 (12)	O8—N4	1.214 (2)
N3—C7	1.312 (2)	O9—N5	1.218 (2)
C1—C2	1.3764 (15)	O10—N5	1.218 (2)
C1—C6	1.374 (2)	N4—C13	1.460 (2)
C2—C3	1.374 (2)	N5—C15	1.4638 (19)
C2—H2	0.93	C11—C12	1.425 (2)
C3—C4	1.367 (2)	C11—C16	1.3841 (19)
C3—H3	0.93	C11—C17	1.493 (2)
C4—C5	1.3668 (15)	C12—C13	1.409 (2)
C5—C6	1.376 (2)	C13—C14	1.376 (2)
C5—H5	0.93	C14—C15	1.372 (2)
C6—H6	0.93	C14—H14	0.93
C7—C8	1.403 (2)	C15—C16	1.379 (2)
C8—C9	1.348 (3)	C16—H16	0.93
C8—H8	0.93

O1—S1—O2	120.50 (6)	C8—C9—C10	133.88 (19)
O1—S1—N2	108.78 (6)	C9—C10—H10a	109.47
O2—S1—N2	104.15 (7)	C9—C10—H10b	109.47
N3—O3—C9	108.94 (14)	C9—C10—H10c	109.47
C4—N1—H1a	102.59 (10)	H10a—C10—H10b	109.47
C4—N1—H1b	107.06 (15)	H10a—C10—H10c	109.47
C4—N1—H1c	107.83 (13)	H10b—C10—H10c	109.47
H1a—N1—H1b	124.65 (16)	C17—O5—H6a	105.28 (11)
H1a—N1—H1c	103.41 (14)	C12—O6—H6a	102.01 (10)
H1b—N1—H1c	110.21 (14)	O7—N4—O8	123.34 (17)
S1—N2—C7	124.43 (12)	O7—N4—C13	118.74 (17)
S1—N2—H2a	113.65 (11)	O8—N4—C13	117.91 (17)
C7—N2—H2a	116.39 (12)	O9—N5—O10	124.03 (14)
O3—N3—C7	104.86 (14)	O9—N5—C15	118.56 (14)
C2—C1—C6	120.38 (14)	O10—N5—C15	117.41 (15)
C1—C2—C3	119.57 (16)	C12—C11—C16	120.99 (14)
C1—C2—H2	120.22	C12—C11—C17	118.93 (12)
C3—C2—H2	120.22	C16—C11—C17	120.07 (13)
C2—C3—C4	119.68 (12)	O6—C12—C11	121.05 (14)
C2—C3—H3	120.16	O6—C12—C13	122.90 (13)
C4—C3—H3	120.16	C11—C12—C13	116.03 (12)
N1—C4—C3	120.80 (10)	N4—C13—C12	120.40 (13)
N1—C4—C5	118.09 (15)	N4—C13—C14	116.57 (15)
C3—C4—C5	121.09 (14)	C12—C13—C14	123.02 (14)
C4—C5—C6	119.44 (16)	C13—C14—C15	118.50 (15)
C4—C5—H5	120.28	C13—C14—H14	120.75
C6—C5—H5	120.28	C15—C14—H14	120.75
C1—C6—C5	119.80 (11)	N5—C15—C14	117.72 (14)
C1—C6—H6	120.1	N5—C15—C16	120.43 (13)
C5—C6—H6	120.1	C14—C15—C16	121.82 (13)
N2—C7—N3	117.05 (14)	C11—C16—C15	119.61 (13)
N2—C7—C8	131.01 (14)	C11—C16—H16	120.19
N3—C7—C8	111.93 (15)	C15—C16—H16	120.19
C7—C8—C9	104.20 (16)	O4—C17—O5	124.29 (16)
C7—C8—H8	127.9	O4—C17—C11	119.59 (13)
C9—C8—H8	127.9	O5—C17—C11	116.11 (13)
O3—C9—C8	110.05 (18)	O5—H6a—O6	156.58 (6)
O3—C9—C10	116.07 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1a···O6ⁱ	1.0015 (14)	2.0683 (10)	3.0655 (17)	173.55 (7)
N1—H1b···N3ⁱⁱ	0.7932 (11)	2.2920 (11)	3.0393 (15)	157.33 (11)
N1—H1c···O4ⁱⁱ	0.8315 (15)	1.8318 (14)	2.663 (2)	177.12 (7)
N2—H2a···O5	0.9703 (12)	1.8440 (10)	2.7852 (15)	162.64 (9)
O5—H6a···O6	1.2945 (12)	1.1837 (11)	2.4268 (16)	156.58 (6)
O5—H6a···C12	1.2945 (12)	1.9326 (15)	2.7490 (19)	115.40 (6)
O6—H6a···O5	1.1837 (11)	1.2945 (12)	2.4268 (16)	156.58 (6)
O6—H6a···C17	1.1837 (11)	2.0485 (15)	2.8249 (19)	119.42 (7)

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

2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ) top

Crystal data top

C₈H₁₃N₂O⁺·C₇H₃N₂O₇⁻·H₂O	Z = 2
M_r = 398.33	F(000) = 416
Triclinic, P1	D_x = 1.497 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6691 (3) Å	Cell parameters from 6994 reflections
b = 11.3831 (4) Å	θ = 2.4–31.6°
c = 12.2900 (5) Å	µ = 0.13 mm⁻¹
α = 89.727 (2)°	T = 100 K
β = 76.771 (2)°	Block, yellow
γ = 76.930 (2)°	0.52 × 0.13 × 0.10 mm
V = 883.62 (6) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4061 independent reflections
Radiation source: fine-focus sealed tube	3042 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.937, T_max = 0.987	k = −14→12
17014 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
R[F > 3σ(F)] = 0.038	Secondary atom site location: difference Fourier map
wR(F) = 0.086	Hydrogen site location: difference Fourier map
S = 1.77	H atoms treated by a mixture of independent and constrained refinement
4061 reflections	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
258 parameters	(Δ/σ)_max = 0.014
0 restraints	Δρ_max = 0.46 e Å⁻³
52 constraints	Δρ_min = −0.23 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters: 15

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

	x	y	z	U_iso*/U_eq
O1	0.30546 (16)	−0.17099 (9)	0.14963 (8)	0.0232 (4)
O2	0.56653 (17)	−0.35718 (9)	0.01361 (9)	0.0316 (4)
O3	0.48656 (18)	−0.36691 (9)	−0.14697 (9)	0.0311 (4)
O4	0.36254 (16)	−0.00313 (9)	−0.33889 (8)	0.0235 (4)
O5	0.23753 (16)	0.16995 (9)	−0.24573 (8)	0.0255 (4)
O6	0.07250 (15)	0.19153 (8)	0.16330 (8)	0.0204 (4)
O7	0.14533 (16)	0.02234 (9)	0.25238 (8)	0.0215 (4)
O8	0.31889 (16)	0.38510 (9)	0.41956 (8)	0.0221 (4)
N1	0.30174 (18)	0.05930 (11)	−0.25094 (10)	0.0185 (4)
N2	0.48606 (19)	−0.31064 (11)	−0.06125 (10)	0.0213 (4)
N3	0.11898 (17)	0.64252 (10)	0.66449 (9)	0.0147 (4)
N4	0.23841 (17)	0.58259 (10)	0.47936 (9)	0.0144 (4)
C1	0.3103 (2)	−0.11910 (12)	0.05547 (11)	0.0151 (5)
C2	0.3895 (2)	−0.18160 (12)	−0.05145 (11)	0.0154 (5)
C3	0.3838 (2)	−0.12419 (13)	−0.15034 (12)	0.0160 (5)
H3a	0.432743	−0.167918	−0.218686	0.0192*
C4	0.3044 (2)	−0.00126 (13)	−0.14615 (11)	0.0150 (5)
C5	0.2281 (2)	0.06626 (13)	−0.04539 (11)	0.0148 (5)
H5a	0.176964	0.149404	−0.044656	0.0177*
C6	0.2290 (2)	0.00871 (12)	0.05379 (11)	0.0140 (5)
C7	0.1429 (2)	0.08121 (13)	0.16123 (11)	0.0159 (5)
C8	0.2598 (2)	0.45829 (12)	0.49910 (12)	0.0158 (5)
C9	0.2070 (2)	0.43367 (13)	0.61582 (11)	0.0160 (5)
H9a	0.221191	0.354014	0.636387	0.0192*
C10	0.1376 (2)	0.52320 (12)	0.69587 (11)	0.0157 (5)
C11	0.1694 (2)	0.67095 (12)	0.55875 (11)	0.0141 (5)
C12	0.1445 (2)	0.80006 (12)	0.52928 (11)	0.0153 (5)
H12a	0.110348	0.85057	0.598371	0.0184*
C13	−0.0374 (2)	0.83589 (13)	0.47019 (13)	0.0224 (5)
H13a	−0.054927	0.919318	0.452627	0.0335*
H13b	−0.165759	0.824046	0.518462	0.0335*
H13c	−0.005734	0.786763	0.402409	0.0335*
C14	0.3509 (2)	0.82298 (12)	0.45745 (12)	0.0195 (5)
H14a	0.461527	0.800548	0.496897	0.0292*
H14b	0.331515	0.907081	0.442205	0.0292*
H14c	0.389104	0.775688	0.38823	0.0292*
C15	0.0772 (2)	0.50600 (13)	0.81821 (12)	0.0221 (5)
H15a	−0.068894	0.545223	0.847126	0.0332*
H15b	0.163895	0.540389	0.855439	0.0332*
H15c	0.097793	0.421295	0.830953	0.0332*
O1w	0.32852 (17)	0.60955 (9)	0.25340 (8)	0.0272 (4)
H1n3	0.061415	0.706878	0.722609	0.037 (5)*
H1n4	0.270467	0.602234	0.406704	0.034 (5)*
H2w1	0.339729	0.675124	0.210779	0.053 (6)*
H1w1	0.381611	0.539911	0.20932	0.055 (6)*
H7	0.211364	−0.063754	0.220331	0.078 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0305 (6)	0.0178 (6)	0.0185 (6)	−0.0038 (5)	−0.0018 (5)	0.0031 (4)
O2	0.0431 (7)	0.0219 (6)	0.0232 (6)	0.0045 (5)	−0.0063 (5)	0.0044 (5)
O3	0.0489 (7)	0.0181 (6)	0.0229 (6)	−0.0036 (5)	−0.0053 (5)	−0.0086 (5)
O4	0.0291 (6)	0.0274 (6)	0.0138 (6)	−0.0083 (5)	−0.0030 (5)	−0.0009 (5)
O5	0.0347 (6)	0.0178 (6)	0.0235 (6)	−0.0045 (5)	−0.0072 (5)	0.0058 (5)
O6	0.0244 (6)	0.0142 (6)	0.0187 (6)	−0.0013 (4)	−0.0004 (4)	−0.0029 (4)
O7	0.0284 (6)	0.0175 (6)	0.0140 (5)	−0.0009 (5)	0.0003 (4)	−0.0003 (4)
O8	0.0321 (6)	0.0137 (5)	0.0176 (6)	−0.0026 (5)	−0.0027 (5)	−0.0025 (4)
N1	0.0182 (6)	0.0202 (7)	0.0186 (7)	−0.0071 (6)	−0.0047 (5)	0.0034 (6)
N2	0.0240 (7)	0.0161 (7)	0.0198 (7)	−0.0035 (6)	0.0019 (6)	0.0001 (6)
N3	0.0168 (6)	0.0123 (6)	0.0136 (6)	−0.0024 (5)	−0.0017 (5)	−0.0006 (5)
N4	0.0172 (6)	0.0117 (6)	0.0129 (6)	−0.0026 (5)	−0.0014 (5)	0.0011 (5)
C1	0.0133 (7)	0.0177 (8)	0.0148 (7)	−0.0064 (6)	−0.0014 (6)	0.0022 (6)
C2	0.0158 (7)	0.0118 (7)	0.0176 (8)	−0.0030 (6)	−0.0017 (6)	−0.0008 (6)
C3	0.0159 (7)	0.0184 (8)	0.0140 (8)	−0.0070 (6)	−0.0012 (6)	−0.0029 (6)
C4	0.0146 (7)	0.0196 (8)	0.0125 (7)	−0.0073 (6)	−0.0030 (6)	0.0033 (6)
C5	0.0121 (7)	0.0137 (7)	0.0188 (8)	−0.0046 (6)	−0.0026 (6)	0.0007 (6)
C6	0.0113 (7)	0.0154 (7)	0.0154 (7)	−0.0048 (6)	−0.0015 (6)	−0.0005 (6)
C7	0.0130 (7)	0.0171 (8)	0.0170 (8)	−0.0048 (6)	−0.0008 (6)	0.0000 (6)
C8	0.0145 (7)	0.0132 (7)	0.0193 (8)	−0.0022 (6)	−0.0036 (6)	0.0001 (6)
C9	0.0177 (7)	0.0110 (7)	0.0187 (8)	−0.0031 (6)	−0.0036 (6)	0.0032 (6)
C10	0.0137 (7)	0.0154 (8)	0.0182 (8)	−0.0033 (6)	−0.0041 (6)	0.0029 (6)
C11	0.0106 (7)	0.0152 (7)	0.0161 (8)	−0.0028 (6)	−0.0026 (6)	−0.0012 (6)
C12	0.0178 (7)	0.0114 (7)	0.0155 (7)	−0.0034 (6)	−0.0014 (6)	−0.0007 (6)
C13	0.0218 (8)	0.0140 (8)	0.0321 (9)	−0.0033 (6)	−0.0089 (7)	0.0052 (7)
C14	0.0210 (8)	0.0141 (8)	0.0218 (8)	−0.0048 (6)	−0.0012 (6)	0.0004 (6)
C15	0.0269 (8)	0.0194 (8)	0.0188 (8)	−0.0047 (7)	−0.0034 (6)	0.0019 (6)
O1w	0.0471 (7)	0.0134 (6)	0.0163 (6)	−0.0043 (5)	−0.0005 (5)	0.0003 (5)

Geometric parameters (Å, º) top

O1—C1	1.2939 (17)	C4—C5	1.3881 (18)
O1—H7	1.4329 (9)	C5—H5a	0.93
O2—N2	1.2279 (17)	C5—C6	1.3816 (19)
O3—N2	1.2346 (17)	C6—C7	1.4844 (18)
O4—N1	1.2304 (15)	C8—C9	1.439 (2)
O5—N1	1.2321 (15)	C9—H9a	0.93
O6—C7	1.2355 (16)	C9—C10	1.3449 (19)
O7—C7	1.3040 (17)	C10—C15	1.4889 (19)
O7—H7	1.0191 (9)	C11—C12	1.4936 (19)
O8—C8	1.2198 (17)	C12—H12a	0.98
N1—C4	1.4597 (18)	C12—C13	1.531 (2)
N2—C2	1.4576 (17)	C12—C14	1.5318 (19)
N3—C10	1.3963 (18)	C13—H13a	0.96
N3—C11	1.3236 (17)	C13—H13b	0.96
N3—H1n3	0.9729 (11)	C13—H13c	0.96
N4—C8	1.4152 (18)	C14—H14a	0.96
N4—C11	1.3303 (17)	C14—H14b	0.96
N4—H1n4	0.9085 (11)	C14—H14c	0.96
C1—C2	1.4259 (18)	C15—H15a	0.96
C1—C6	1.4349 (19)	C15—H15b	0.96
C2—C3	1.381 (2)	C15—H15c	0.96
C3—H3a	0.93	O1w—H2w1	0.9169 (10)
C3—C4	1.3763 (19)	O1w—H1w1	0.9146 (10)

C1—O1—H7	96.54 (8)	N4—C8—C9	113.60 (12)
C7—O7—H7	101.27 (9)	C8—C9—H9a	119.24
O4—N1—O5	124.04 (12)	C8—C9—C10	121.51 (13)
O4—N1—C4	118.12 (11)	H9a—C9—C10	119.24
O5—N1—C4	117.84 (11)	N3—C10—C9	118.95 (12)
O2—N2—O3	123.42 (12)	N3—C10—C15	116.00 (11)
O2—N2—C2	119.16 (12)	C9—C10—C15	125.06 (13)
O3—N2—C2	117.39 (12)	N3—C11—N4	118.76 (12)
C10—N3—C11	122.45 (11)	N3—C11—C12	120.45 (12)
C10—N3—H1n3	118.37 (11)	N4—C11—C12	120.78 (12)
C11—N3—H1n3	119.14 (11)	C11—C12—H12a	108.71
C8—N4—C11	124.69 (12)	C11—C12—C13	109.61 (13)
C8—N4—H1n4	116.55 (11)	C11—C12—C14	111.42 (10)
C11—N4—H1n4	118.72 (12)	H12a—C12—C13	108.78
O1—C1—C2	124.06 (12)	H12a—C12—C14	106.87
O1—C1—C6	120.40 (11)	C13—C12—C14	111.36 (12)
C2—C1—C6	115.53 (12)	C12—C13—H13a	109.47
N2—C2—C1	120.85 (12)	C12—C13—H13b	109.47
N2—C2—C3	116.56 (11)	C12—C13—H13c	109.47
C1—C2—C3	122.58 (12)	H13a—C13—H13b	109.47
C2—C3—H3a	120.52	H13a—C13—H13c	109.47
C2—C3—C4	118.97 (12)	H13b—C13—H13c	109.47
H3a—C3—C4	120.52	C12—C14—H14a	109.47
N1—C4—C3	118.77 (12)	C12—C14—H14b	109.47
N1—C4—C5	119.38 (12)	C12—C14—H14c	109.47
C3—C4—C5	121.85 (13)	H14a—C14—H14b	109.47
C4—C5—H5a	120.33	H14a—C14—H14c	109.47
C4—C5—C6	119.34 (12)	H14b—C14—H14c	109.47
H5a—C5—C6	120.33	C10—C15—H15a	109.47
C1—C6—C5	121.71 (12)	C10—C15—H15b	109.47
C1—C6—C7	119.30 (12)	C10—C15—H15c	109.47
C5—C6—C7	118.99 (12)	H15a—C15—H15b	109.47
O6—C7—O7	122.20 (12)	H15a—C15—H15c	109.47
O6—C7—C6	121.26 (12)	H15b—C15—H15c	109.47
O7—C7—C6	116.54 (12)	H2w1—O1w—H1w1	110.00 (10)
O8—C8—N4	119.14 (12)	O1—H7—O7	165.94 (7)
O8—C8—C9	127.26 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12a···O7ⁱ	0.98	2.42	3.3068 (15)	151
N3—H1n3···O6ⁱ	0.9729 (11)	1.7539 (9)	2.7182 (14)	170.48 (8)
N4—H1n4···O1w	0.9085 (11)	1.8401 (10)	2.7348 (15)	167.76 (8)
O1w—H2w1···O1ⁱⁱ	0.9169 (10)	1.8895 (10)	2.7886 (14)	166.21 (6)
O1w—H1w1···O3ⁱⁱⁱ	0.9146 (10)	2.0399 (10)	2.9352 (14)	165.84 (7)
O7—H7···O1	1.0191 (9)	1.4329 (9)	2.4340 (13)	165.94 (7)

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

1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR) top

Crystal data top

C₉H₁₇N₂⁺·C₇H₃N₂O₇⁻	F(000) = 800
M_r = 380.35	D_x = 1.489 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabc	Cell parameters from 1891 reflections
a = 6.1537 (3) Å	θ = 3.5–26.6°
b = 19.1541 (14) Å	µ = 0.12 mm⁻¹
c = 14.5527 (11) Å	T = 200 K
β = 98.343 (6)°	Needle, yellow
V = 1697.2 (2) Å³	0.30 × 0.13 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Gemini-S CCD-detector diffractometer	3339 independent reflections
Graphite monochromator	1976 reflections with I > 3σ(I)
Detector resolution: 16.067 pixels mm^-1	R_int = 0.034
ω scans	θ_max = 26.0°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −7→7
T_min = 0.920, T_max = 0.990	k = −23→23
7800 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0004I²)
S = 1.33	(Δ/σ)_max = 0.005
3339 reflections	Δρ_max = 0.36 e Å⁻³
268 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
98 constraints	Extinction coefficient: 2200 (700)
Primary atom site location: structure-invariant direct methods

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Number of fixed parameters : 10

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O2b	0.8418 (3)	0.56169 (11)	0.78950 (14)	0.0440 (8)	0.727 (4)
H61b	0.852107	0.560819	0.76707	0.0359*	0.273 (4)
O21b	0.7735 (8)	0.6569 (3)	0.4912 (4)	0.048 (2)	0.273 (4)
H6b	0.805712	0.644967	0.507207	0.0328*	0.727 (4)
O11b	0.5083 (2)	0.68884 (8)	0.59278 (11)	0.0444 (6)
O12b	0.5447 (2)	0.64534 (8)	0.73586 (12)	0.0524 (7)
O31b	1.1108 (3)	0.45706 (10)	0.81717 (14)	0.0829 (9)
O32b	1.4073 (3)	0.47245 (10)	0.75770 (13)	0.0775 (8)
O51b	1.3288 (3)	0.55869 (9)	0.44602 (12)	0.0603 (7)
O52b	1.0707 (3)	0.63212 (10)	0.39870 (12)	0.0680 (8)
N3b	1.2111 (3)	0.48284 (10)	0.76049 (14)	0.0472 (8)
N5b	1.1654 (3)	0.59180 (10)	0.45701 (14)	0.0418 (7)
C1b	0.8002 (3)	0.60956 (10)	0.63903 (15)	0.0264 (7)
C2b	0.9062 (3)	0.56604 (11)	0.70954 (15)	0.0299 (7)
C3b	1.0952 (3)	0.53063 (10)	0.69140 (15)	0.0309 (7)
C4b	1.1814 (3)	0.53946 (10)	0.61042 (15)	0.0309 (7)
C5b	1.0736 (3)	0.58234 (10)	0.54290 (14)	0.0271 (7)
C6b	0.8810 (3)	0.61681 (10)	0.55538 (15)	0.0273 (7)
C11b	0.6030 (3)	0.65080 (11)	0.65583 (18)	0.0351 (8)
N1a	−0.1521 (2)	0.82026 (8)	0.63826 (12)	0.0293 (6)
N8a	0.1721 (2)	0.76019 (9)	0.67283 (12)	0.0373 (7)
C2a	−0.3261 (3)	0.85089 (11)	0.57022 (15)	0.0370 (8)
C3a	−0.2602 (3)	0.91805 (11)	0.52679 (15)	0.0401 (8)
C4a	−0.1188 (3)	0.90791 (11)	0.45061 (16)	0.0417 (8)
C5a	0.0933 (3)	0.86805 (11)	0.48032 (14)	0.0401 (8)
C6a	0.0611 (3)	0.79367 (11)	0.51423 (14)	0.0344 (8)
C7a	0.0226 (3)	0.79087 (10)	0.61288 (14)	0.0268 (7)
C9a	0.1394 (8)	0.7480 (3)	0.7694 (4)	0.0377 (17)	0.687 (4)
C10a	0.0234 (5)	0.8112 (2)	0.8006 (2)	0.0388 (12)	0.687 (4)
C11a	−0.1865 (3)	0.82334 (13)	0.73606 (16)	0.0375 (8)
C13a	0.192 (2)	0.7733 (6)	0.7752 (10)	0.0377 (17)	0.313 (4)
C12a	−0.0453 (12)	0.7700 (5)	0.7962 (6)	0.0388 (12)	0.313 (4)
H4b	1.313123	0.516393	0.601144	0.0371*
H8a	0.304017	0.743029	0.652706	0.073 (8)*
H10a	0.119515	0.852593	0.800333	0.0466*	0.686
H21a	−0.458393	0.859249	0.600103	0.0444*
H22a	−0.373911	0.816372	0.520773	0.0444*
H31a	−0.393523	0.944805	0.502041	0.0481*
H32a	−0.182575	0.948658	0.575716	0.0481*
H41a	−0.084564	0.95395	0.425285	0.0501*
H42a	−0.20539	0.883982	0.397103	0.0501*
H51a	0.180506	0.866759	0.428286	0.0482*
H52a	0.186838	0.894538	0.52943	0.0482*
H61a	0.191356	0.765112	0.506561	0.0413*
H62a	−0.063947	0.77162	0.474177	0.0413*
H91a	0.046176	0.706149	0.772504	0.0452*	0.687 (4)
H92a	0.283833	0.74265	0.808712	0.0452*	0.687 (4)
H11a	−0.009873	0.803439	0.864351	0.0466*	0.686
H12a	−0.318 (2)	0.7965 (9)	0.7425 (13)	0.045*
H13a	−0.230 (3)	0.8711 (6)	0.7485 (13)	0.045*
H14a	−0.105082	0.7226	0.782436	0.0466*	0.313 (4)
H15a	−0.047311	0.780768	0.862598	0.0466*	0.313 (4)
H16a	0.27893	0.735519	0.809131	0.0452*	0.313 (4)
H17a	0.251697	0.820686	0.789237	0.0452*	0.313 (4)
H21b	0.621837	0.678052	0.538628	0.082 (11)*	0.273 (4)
H2b	0.702896	0.598291	0.774475	0.082 (11)*	0.727 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2b	0.0481 (12)	0.0570 (16)	0.0296 (15)	0.0087 (11)	0.0152 (10)	0.0091 (11)
O21b	0.045 (3)	0.053 (4)	0.046 (4)	0.006 (3)	0.006 (3)	0.023 (3)
O11b	0.0369 (8)	0.0391 (10)	0.0583 (12)	0.0136 (7)	0.0102 (8)	0.0073 (9)
O12b	0.0488 (9)	0.0643 (12)	0.0488 (12)	0.0091 (8)	0.0232 (8)	−0.0030 (9)
O31b	0.0796 (13)	0.0853 (16)	0.0753 (16)	−0.0256 (11)	−0.0175 (11)	0.0533 (13)
O32b	0.0728 (12)	0.0903 (16)	0.0642 (14)	0.0483 (11)	−0.0074 (10)	0.0050 (11)
O51b	0.0542 (10)	0.0650 (12)	0.0694 (13)	0.0077 (9)	0.0350 (9)	−0.0110 (10)
O52b	0.0926 (13)	0.0722 (14)	0.0455 (12)	0.0171 (11)	0.0314 (10)	0.0241 (10)
N3b	0.0575 (13)	0.0347 (13)	0.0432 (15)	0.0005 (11)	−0.0137 (11)	−0.0004 (10)
N5b	0.0476 (11)	0.0400 (13)	0.0414 (13)	−0.0046 (10)	0.0193 (10)	−0.0067 (10)
C1b	0.0265 (10)	0.0220 (11)	0.0303 (13)	−0.0029 (9)	0.0024 (9)	−0.0023 (10)
C2b	0.0337 (11)	0.0267 (12)	0.0294 (14)	−0.0061 (10)	0.0050 (10)	−0.0023 (10)
C3b	0.0361 (11)	0.0233 (12)	0.0304 (14)	0.0002 (9)	−0.0053 (10)	0.0025 (10)
C4b	0.0257 (10)	0.0240 (12)	0.0413 (15)	−0.0013 (9)	−0.0005 (10)	−0.0053 (11)
C5b	0.0295 (10)	0.0254 (12)	0.0274 (13)	−0.0052 (9)	0.0073 (9)	−0.0017 (10)
C6b	0.0298 (10)	0.0218 (12)	0.0290 (13)	−0.0028 (9)	−0.0003 (9)	0.0007 (10)
C11b	0.0297 (11)	0.0296 (13)	0.0464 (16)	−0.0042 (10)	0.0070 (11)	−0.0061 (12)
N1a	0.0249 (8)	0.0327 (11)	0.0305 (11)	0.0026 (8)	0.0041 (8)	0.0000 (9)
N8a	0.0332 (9)	0.0493 (12)	0.0291 (12)	0.0137 (9)	0.0037 (8)	0.0056 (9)
C2a	0.0243 (10)	0.0400 (14)	0.0451 (15)	0.0063 (10)	−0.0002 (10)	−0.0020 (12)
C3a	0.0374 (12)	0.0331 (14)	0.0465 (16)	0.0071 (10)	−0.0044 (11)	0.0000 (11)
C4a	0.0450 (12)	0.0397 (15)	0.0370 (15)	−0.0028 (11)	−0.0060 (11)	0.0087 (11)
C5a	0.0368 (11)	0.0526 (16)	0.0319 (14)	−0.0008 (11)	0.0079 (10)	0.0091 (12)
C6a	0.0355 (11)	0.0411 (15)	0.0262 (13)	0.0079 (10)	0.0032 (9)	−0.0057 (11)
C7a	0.0283 (10)	0.0224 (12)	0.0291 (13)	−0.0012 (9)	0.0025 (9)	−0.0030 (10)
C9a	0.040 (3)	0.041 (4)	0.0304 (18)	−0.001 (2)	−0.001 (2)	0.004 (3)
C10a	0.049 (2)	0.042 (2)	0.0270 (17)	−0.0043 (18)	0.0083 (15)	−0.0029 (19)
C11a	0.0367 (12)	0.0426 (15)	0.0364 (15)	0.0003 (11)	0.0161 (11)	−0.0056 (12)
C13a	0.040 (3)	0.041 (4)	0.0304 (18)	−0.001 (2)	−0.001 (2)	0.004 (3)
C12a	0.049 (2)	0.042 (2)	0.0270 (17)	−0.0043 (18)	0.0083 (15)	−0.0029 (19)

Geometric parameters (Å, º) top

O2b—C2b	1.285 (3)	C2a—H22a	0.99
O2b—H2b	1.103 (2)	C3a—C4a	1.518 (3)
H61b—C2b	0.95	C3a—H31a	0.99
O21b—C6b	1.311 (6)	C3a—H32a	0.99
O21b—H21b	1.303 (6)	C4a—C5a	1.520 (3)
H6b—C6b	0.95	C4a—H41a	0.99
O11b—C11b	1.248 (3)	C4a—H42a	0.99
O11b—H21b	1.1454 (16)	C5a—C6a	1.530 (3)
O12b—C11b	1.272 (3)	C5a—H51a	0.99
O12b—H2b	1.3846 (15)	C5a—H52a	0.99
O31b—N3b	1.205 (3)	C6a—C7a	1.490 (3)
O32b—N3b	1.230 (3)	C6a—H61a	0.99
O51b—N5b	1.219 (3)	C6a—H62a	0.99
O52b—N5b	1.230 (3)	C9a—C10a	1.508 (6)
N3b—C3b	1.466 (3)	C9a—C13a	0.581 (13)
N5b—C5b	1.456 (3)	C9a—C12a	1.323 (10)
C1b—C2b	1.407 (3)	C9a—H91a	0.99
C1b—C6b	1.387 (3)	C9a—H92a	0.99
C1b—C11b	1.497 (3)	C9a—H16a	0.9922
C2b—C3b	1.404 (3)	C10a—C11a	1.501 (4)
C3b—C4b	1.371 (3)	C10a—C13a	1.358 (14)
C4b—C5b	1.375 (3)	C10a—H10a	0.99
C4b—H4b	0.95	C10a—H11a	0.99
C5b—C6b	1.392 (3)	C10a—H15a	1.207
N1a—C2a	1.471 (2)	C11a—C12a	1.530 (8)
N1a—C7a	1.313 (2)	C11a—H12a	0.977 (15)
N1a—C11a	1.470 (3)	C11a—H13a	0.978 (13)
N8a—C7a	1.311 (2)	C13a—C12a	1.534 (16)
N8a—C9a	1.467 (6)	C13a—H92a	0.9083
N8a—C13a	1.498 (15)	C13a—H16a	0.99
N8a—H8a	0.9604 (17)	C13a—H17a	0.99
C2a—C3a	1.514 (3)	C12a—H14a	0.99
C2a—H21a	0.99	C12a—H15a	0.99

H6b—O21b—H21b	102.88	N8a—C9a—C13a	81.6 (16)
C11b—O12b—H2b	98.61 (14)	N8a—C9a—C12a	118.3 (5)
O31b—N3b—O32b	124.0 (2)	N8a—C9a—H91a	109.47
O31b—N3b—C3b	118.6 (2)	N8a—C9a—H92a	109.47
O32b—N3b—C3b	117.4 (2)	N8a—C9a—H14a	114.78
O51b—N5b—O52b	123.6 (2)	N8a—C9a—H16a	111.65
O51b—N5b—C5b	118.57 (18)	C10a—C9a—H91a	109.47
O52b—N5b—C5b	117.83 (18)	C10a—C9a—H92a	109.47
C2b—C1b—C6b	120.82 (17)	C13a—C9a—C12a	99.9 (15)
C2b—C1b—C11b	119.6 (2)	C13a—C9a—H91a	168.74
C6b—C1b—C11b	119.51 (18)	C13a—C9a—H14a	137.56
O2b—C2b—C1b	121.84 (19)	C12a—C9a—H92a	126.91
O2b—C2b—C3b	120.77 (19)	C12a—C9a—H16a	127.82
H61b—C2b—C1b	121.37	H91a—C9a—H92a	111.59
H61b—C2b—C3b	121.37	H14a—C9a—H16a	126.91
C1b—C2b—C3b	117.3 (2)	H14a—C9a—H17a	129.78
N3b—C3b—C2b	120.4 (2)	H16a—C9a—H17a	77.55
N3b—C3b—C4b	117.12 (18)	C9a—C10a—C11a	109.8 (3)
C2b—C3b—C4b	122.44 (18)	C11a—C10a—C13a	122.2 (6)
C3b—C4b—C5b	118.75 (18)	C11a—C10a—H10a	109.47
C3b—C4b—H4b	120.62	C11a—C10a—H11a	109.47
C5b—C4b—H4b	120.62	C11a—C10a—H17a	132.02
N5b—C5b—C4b	118.74 (17)	C13a—C10a—H11a	116.43
N5b—C5b—C6b	119.80 (17)	C13a—C10a—H15a	108.54
C4b—C5b—C6b	121.5 (2)	C12a—C10a—H17a	124.07
O21b—C6b—C1b	118.4 (3)	H10a—C10a—H11a	109.16
O21b—C6b—C5b	122.4 (3)	H10a—C10a—H15a	132.06
H6b—C6b—C1b	120.41	H11a—C10a—H17a	117.48
H6b—C6b—C5b	120.41	H15a—C10a—H17a	127.34
C1b—C6b—C5b	119.17 (18)	N1a—C11a—C10a	111.6 (2)
O11b—C11b—O12b	123.9 (2)	N1a—C11a—C12a	112.2 (4)
O11b—C11b—C1b	119.4 (2)	N1a—C11a—H12a	108.1 (11)
O12b—C11b—C1b	116.70 (19)	N1a—C11a—H13a	107.3 (12)
C2a—N1a—C7a	121.83 (17)	C10a—C11a—H12a	120.7 (10)
C2a—N1a—C11a	116.29 (16)	C10a—C11a—H13a	105.2 (10)
C7a—N1a—C11a	121.87 (16)	C12a—C11a—H13a	131.8 (11)
C7a—N8a—C9a	121.9 (2)	H12a—C11a—H13a	102.9 (15)
C7a—N8a—C13a	122.3 (5)	N8a—C13a—C9a	75.8 (15)
C7a—N8a—H8a	119.53 (19)	N8a—C13a—C10a	114.0 (9)
C9a—N8a—C13a	22.6 (5)	N8a—C13a—C12a	104.5 (8)
C9a—N8a—H8a	118.5 (2)	N8a—C13a—H10a	113.12
C13a—N8a—H8a	114.3 (5)	N8a—C13a—H92a	112.32
N1a—C2a—C3a	114.01 (15)	N8a—C13a—H16a	109.47
N1a—C2a—H21a	109.47	N8a—C13a—H17a	109.47
N1a—C2a—H22a	109.47	C9a—C13a—H10a	130.08
C3a—C2a—H21a	109.47	C9a—C13a—H17a	167.66
C3a—C2a—H22a	109.47	C10a—C13a—H92a	129.79
H21a—C2a—H22a	104.52	C10a—C13a—H16a	129.35
C2a—C3a—C4a	114.39 (18)	C12a—C13a—H92a	113.84
C2a—C3a—H31a	109.47	C12a—C13a—H16a	109.47
C2a—C3a—H32a	109.47	C12a—C13a—H17a	109.47
C4a—C3a—H31a	109.47	H10a—C13a—H91a	126.53
C4a—C3a—H32a	109.47	H10a—C13a—H92a	130.35
H31a—C3a—H32a	104.05	H10a—C13a—H16a	135.32
C3a—C4a—C5a	114.58 (18)	H92a—C13a—H17a	107.21
C3a—C4a—H41a	109.47	H16a—C13a—H17a	114.05
C3a—C4a—H42a	109.47	C9a—C12a—C11a	119.1 (6)
C5a—C4a—H41a	109.47	C9a—C12a—H11a	111.16
C5a—C4a—H42a	109.47	C9a—C12a—H15a	119.13
H41a—C4a—H42a	103.83	C10a—C12a—H91a	125.59
C4a—C5a—C6a	114.44 (16)	C10a—C12a—H14a	169.66
C4a—C5a—H51a	109.47	C11a—C12a—C13a	109.6 (7)
C4a—C5a—H52a	109.47	C11a—C12a—H91a	130.75
C6a—C5a—H51a	109.47	C11a—C12a—H14a	109.47
C6a—C5a—H52a	109.47	C11a—C12a—H15a	109.47
H51a—C5a—H52a	104	C13a—C12a—H14a	109.47
C5a—C6a—C7a	112.99 (17)	C13a—C12a—H15a	109.47
C5a—C6a—H61a	109.47	H91a—C12a—H11a	130.35
C5a—C6a—H62a	109.47	H91a—C12a—H15a	118.71
C7a—C6a—H61a	109.47	H11a—C12a—H14a	133.54
C7a—C6a—H62a	109.47	H14a—C12a—H15a	109.31
H61a—C6a—H62a	105.71	O21b—H21b—O11b	167.3 (3)
N1a—C7a—N8a	121.93 (19)	H6b—H21b—O11b	152.98
N1a—C7a—C6a	120.45 (16)	O2b—H2b—O12b	166.81 (13)
N8a—C7a—C6a	117.59 (17)	H61b—H2b—O12b	150.18
N8a—C9a—C10a	107.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8a—H8a···O11b	0.9604 (17)	1.9329 (15)	2.864 (2)	162.83 (11)
C10a—H10a···O32bⁱ	0.99	2.44	3.248 (4)	138
C2a—H21a···O31bⁱⁱ	0.99	2.48	3.275 (3)	137
C6a—H62a···O21bⁱⁱⁱ	0.99	2.44	3.152 (6)	128
C10a—H11a···O21b^iv	0.99	2.47	3.033 (7)	116
O21b—H21b···O11b	1.303 (6)	1.1454 (16)	2.433 (6)	167.3 (3)
O11b—H21b···O21b	1.1454 (16)	1.303 (6)	2.433 (6)	167.3 (3)
O12b—H2b···O2b	1.3846 (15)	1.103 (2)	2.471 (2)	166.81 (13)

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

4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE) top

Crystal data top

C₂₆H₂₉N₂⁺·C₇H₃N₂O₇⁻	F(000) = 1256
M_r = 596.63	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.5648 (3) Å	Cell parameters from 9909 reflections
b = 12.9374 (3) Å	θ = 2.3–28.3°
c = 16.1619 (3) Å	µ = 0.10 mm⁻¹
β = 103.900 (1)°	T = 200 K
V = 2956.22 (11) Å³	Block, yellow
Z = 4	0.51 × 0.26 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	7344 independent reflections
Radiation source: fine-focus sealed tube	5724 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.015
φ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→19
T_min = 0.932, T_max = 1.000	k = −17→17
29552 measured reflections	l = −21→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F > 3σ(F)] = 0.054	Hydrogen site location: difference Fourier map
wR(F) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.80	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0063999998I²)
7344 reflections	(Δ/σ)_max = 0.044
399 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³
120 constraints

Special details top

Refinement. Number of fixed parameters 6

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

	x	y	z	U_iso*/U_eq
N1	0.25627 (8)	0.71181 (9)	0.31343 (7)	0.0246 (3)
H71	0.30128	0.669474	0.349979	0.035 (4)*
N2	0.10023 (8)	0.56683 (9)	0.26575 (7)	0.0233 (3)
C1	0.29865 (11)	0.95151 (12)	0.41661 (10)	0.0334 (5)
H1a	0.245898	0.980932	0.377422	0.0401*
C2	0.33463 (11)	0.86695 (12)	0.39170 (10)	0.0322 (5)
H2	0.386765	0.835478	0.430202	0.0386*
C3	0.29839 (12)	0.81754 (12)	0.30656 (10)	0.0333 (5)
H3a	0.350521	0.811391	0.27725	0.04*
H3b	0.250048	0.862741	0.270514	0.04*
C4	0.17112 (10)	0.71678 (11)	0.34935 (9)	0.0281 (4)
H4a	0.123241	0.762704	0.313566	0.0337*
H4b	0.189039	0.745897	0.40767	0.0337*
C5	0.12943 (10)	0.61031 (11)	0.35226 (9)	0.0271 (4)
H5a	0.07387	0.614805	0.377337	0.0326*
H5b	0.177161	0.564522	0.388386	0.0326*
C6	0.18571 (10)	0.55563 (11)	0.23345 (9)	0.0262 (4)
H6a	0.231171	0.509606	0.271816	0.0315*
H6b	0.168931	0.5233	0.176272	0.0315*
C7	0.23149 (10)	0.65944 (12)	0.22789 (9)	0.0282 (4)
H7a	0.289537	0.649813	0.207068	0.0338*
H7b	0.187639	0.703827	0.186493	0.0338*
C8	0.05326 (9)	0.46528 (10)	0.26756 (8)	0.0230 (4)
H8	0.099282	0.417266	0.304542	0.0276*
C11	0.33145 (11)	1.00535 (12)	0.49876 (10)	0.0326 (5)
C12	0.41578 (13)	0.97941 (14)	0.55685 (10)	0.0391 (5)
H12	0.454927	0.926517	0.543205	0.047*
C13	0.44278 (15)	1.03053 (17)	0.63457 (11)	0.0502 (6)
H13	0.499799	1.011658	0.674094	0.0603*
C14	0.38752 (17)	1.10810 (17)	0.65451 (12)	0.0554 (7)
H14	0.40688	1.143158	0.707495	0.0665*
C15	0.30389 (15)	1.13552 (16)	0.59798 (13)	0.0516 (7)
H15	0.265849	1.18931	0.61197	0.0619*
C16	0.27570 (13)	1.08400 (13)	0.52053 (11)	0.0397 (5)
H16	0.217882	1.102436	0.481949	0.0476*
C21	−0.03166 (9)	0.47504 (10)	0.30647 (8)	0.0240 (4)
C22	−0.04272 (11)	0.40385 (12)	0.36763 (10)	0.0315 (5)
H22	0.003276	0.351198	0.385315	0.0378*
C23	−0.12077 (12)	0.40899 (13)	0.40333 (11)	0.0388 (5)
H23	−0.127745	0.359826	0.445056	0.0466*
C24	−0.18805 (12)	0.48544 (13)	0.37818 (11)	0.0385 (5)
H24	−0.241677	0.488365	0.401911	0.0461*
C25	−0.17687 (11)	0.55719 (12)	0.31859 (11)	0.0351 (5)
H25	−0.222711	0.610174	0.301738	0.0421*
C26	−0.09910 (10)	0.55304 (11)	0.28271 (9)	0.0286 (4)
H26	−0.091899	0.603396	0.241958	0.0344*
C31	0.02520 (10)	0.41880 (11)	0.17810 (9)	0.0248 (4)
C32	0.06690 (11)	0.32720 (12)	0.16027 (10)	0.0331 (5)
H32	0.112496	0.2938	0.204043	0.0397*
C33	0.04254 (13)	0.28416 (13)	0.07918 (11)	0.0392 (5)
H33	0.071842	0.221893	0.067798	0.047*
C34	−0.02351 (12)	0.33108 (13)	0.01557 (10)	0.0379 (5)
H34	−0.039638	0.301886	−0.039979	0.0455*
C35	−0.06672 (12)	0.42142 (14)	0.03267 (10)	0.0385 (5)
H35	−0.113709	0.453238	−0.01092	0.0461*
C36	−0.04162 (11)	0.46550 (12)	0.11316 (10)	0.0321 (5)
H36	−0.070483	0.528311	0.123929	0.0386*
O1	0.63327 (8)	0.37352 (10)	0.53505 (8)	0.0392 (4)
O2	0.58197 (10)	0.44006 (14)	0.67133 (9)	0.0614 (6)
O3	0.43608 (10)	0.48129 (12)	0.65684 (9)	0.0549 (5)
O4	0.19464 (9)	0.32143 (13)	0.44743 (10)	0.0569 (5)
O5	0.22764 (11)	0.24248 (13)	0.34091 (10)	0.0631 (6)
O6	0.54745 (10)	0.23529 (12)	0.30214 (8)	0.0518 (5)
O7	0.66627 (9)	0.28940 (12)	0.40564 (9)	0.0507 (5)
N3	0.49861 (10)	0.43835 (11)	0.63197 (9)	0.0379 (4)
N4	0.25133 (10)	0.29121 (12)	0.40756 (10)	0.0428 (5)
C9	0.57563 (13)	0.27360 (13)	0.37128 (12)	0.0398 (6)
C41	0.54458 (10)	0.35627 (11)	0.50735 (10)	0.0298 (4)
C42	0.50987 (11)	0.30564 (12)	0.42622 (10)	0.0314 (5)
C43	0.41587 (11)	0.28489 (12)	0.39522 (10)	0.0329 (5)
H43	0.395087	0.249901	0.342348	0.0394*
C44	0.35106 (10)	0.31453 (12)	0.44039 (10)	0.0313 (4)
C45	0.37850 (10)	0.36477 (12)	0.51759 (10)	0.0305 (4)
H45	0.332901	0.38543	0.547596	0.0366*
C46	0.47336 (11)	0.38456 (11)	0.55054 (9)	0.0290 (4)
H7	0.676841	0.321683	0.458063	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0221 (6)	0.0282 (6)	0.0236 (5)	−0.0039 (4)	0.0055 (4)	−0.0028 (4)
N2	0.0209 (5)	0.0268 (6)	0.0227 (5)	−0.0035 (4)	0.0063 (4)	−0.0032 (4)
C1	0.0300 (8)	0.0358 (8)	0.0314 (7)	−0.0037 (6)	0.0017 (6)	−0.0003 (6)
C2	0.0301 (7)	0.0308 (7)	0.0334 (7)	−0.0076 (6)	0.0033 (6)	0.0004 (6)
C3	0.0391 (8)	0.0304 (7)	0.0318 (7)	−0.0113 (6)	0.0111 (6)	−0.0022 (6)
C4	0.0216 (6)	0.0331 (7)	0.0302 (7)	−0.0026 (5)	0.0075 (5)	−0.0076 (5)
C5	0.0248 (7)	0.0337 (7)	0.0241 (6)	−0.0051 (5)	0.0082 (5)	−0.0053 (5)
C6	0.0232 (6)	0.0304 (7)	0.0265 (6)	−0.0032 (5)	0.0088 (5)	−0.0047 (5)
C7	0.0285 (7)	0.0344 (7)	0.0223 (6)	−0.0060 (6)	0.0073 (5)	−0.0045 (5)
C8	0.0197 (6)	0.0247 (6)	0.0245 (6)	0.0003 (5)	0.0054 (5)	0.0010 (5)
C11	0.0357 (8)	0.0306 (7)	0.0307 (7)	−0.0080 (6)	0.0064 (6)	0.0006 (6)
C12	0.0398 (9)	0.0415 (9)	0.0337 (8)	−0.0067 (7)	0.0042 (7)	0.0007 (7)
C13	0.0523 (11)	0.0604 (12)	0.0319 (8)	−0.0142 (9)	−0.0018 (8)	0.0005 (8)
C14	0.0691 (14)	0.0629 (13)	0.0354 (9)	−0.0230 (10)	0.0149 (9)	−0.0159 (8)
C15	0.0584 (12)	0.0455 (10)	0.0562 (11)	−0.0106 (9)	0.0242 (10)	−0.0151 (8)
C16	0.0392 (9)	0.0350 (8)	0.0444 (9)	−0.0049 (7)	0.0090 (7)	−0.0039 (7)
C21	0.0213 (6)	0.0250 (6)	0.0255 (6)	−0.0020 (5)	0.0050 (5)	−0.0024 (5)
C22	0.0311 (7)	0.0329 (8)	0.0325 (7)	0.0030 (6)	0.0114 (6)	0.0046 (6)
C23	0.0426 (9)	0.0390 (9)	0.0413 (9)	0.0005 (7)	0.0228 (7)	0.0058 (7)
C24	0.0344 (8)	0.0391 (8)	0.0493 (9)	−0.0028 (6)	0.0245 (7)	−0.0078 (7)
C25	0.0278 (7)	0.0336 (8)	0.0447 (9)	0.0044 (6)	0.0104 (6)	−0.0058 (6)
C26	0.0269 (7)	0.0271 (7)	0.0323 (7)	0.0015 (5)	0.0079 (6)	0.0002 (5)
C31	0.0226 (6)	0.0253 (6)	0.0282 (6)	−0.0049 (5)	0.0093 (5)	−0.0016 (5)
C32	0.0327 (8)	0.0296 (7)	0.0367 (8)	0.0017 (6)	0.0076 (6)	−0.0021 (6)
C33	0.0437 (9)	0.0299 (8)	0.0463 (9)	−0.0014 (7)	0.0154 (8)	−0.0097 (7)
C34	0.0452 (9)	0.0381 (9)	0.0313 (8)	−0.0104 (7)	0.0109 (7)	−0.0090 (6)
C35	0.0387 (9)	0.0451 (9)	0.0283 (7)	−0.0015 (7)	0.0017 (7)	−0.0024 (7)
C36	0.0316 (8)	0.0337 (8)	0.0310 (7)	0.0020 (6)	0.0073 (6)	−0.0020 (6)
O1	0.0242 (6)	0.0466 (7)	0.0449 (6)	−0.0022 (5)	0.0046 (5)	0.0065 (5)
O2	0.0364 (7)	0.0954 (12)	0.0457 (8)	0.0021 (7)	−0.0029 (6)	−0.0243 (7)
O3	0.0459 (8)	0.0698 (9)	0.0453 (7)	0.0153 (7)	0.0038 (6)	−0.0171 (6)
O4	0.0239 (6)	0.0732 (10)	0.0713 (9)	0.0049 (6)	0.0067 (6)	−0.0008 (8)
O5	0.0465 (8)	0.0774 (11)	0.0531 (8)	−0.0103 (7)	−0.0120 (7)	−0.0150 (7)
O6	0.0595 (9)	0.0612 (9)	0.0400 (7)	0.0066 (7)	0.0226 (6)	−0.0026 (6)
O7	0.0391 (7)	0.0619 (9)	0.0567 (8)	0.0007 (6)	0.0223 (6)	−0.0035 (6)
N3	0.0355 (7)	0.0405 (8)	0.0347 (7)	0.0038 (6)	0.0023 (6)	−0.0023 (6)
N4	0.0303 (7)	0.0466 (8)	0.0442 (8)	−0.0012 (6)	−0.0056 (6)	0.0040 (6)
C9	0.0393 (9)	0.0352 (8)	0.0491 (10)	0.0046 (7)	0.0190 (8)	0.0095 (7)
C41	0.0232 (7)	0.0277 (7)	0.0368 (7)	0.0028 (5)	0.0038 (6)	0.0099 (6)
C42	0.0330 (8)	0.0293 (7)	0.0345 (7)	0.0049 (6)	0.0133 (6)	0.0074 (6)
C43	0.0370 (8)	0.0322 (8)	0.0284 (7)	0.0011 (6)	0.0059 (6)	0.0030 (6)
C44	0.0238 (7)	0.0334 (8)	0.0333 (7)	0.0012 (5)	0.0000 (6)	0.0037 (6)
C45	0.0255 (7)	0.0325 (7)	0.0333 (7)	0.0060 (6)	0.0067 (6)	0.0030 (6)
C46	0.0282 (7)	0.0282 (7)	0.0282 (7)	0.0018 (5)	0.0017 (6)	0.0016 (5)

Geometric parameters (Å, º) top

N1—H71	0.9448 (11)	C16—H16	0.95
N1—C3	1.5141 (19)	C21—C22	1.388 (2)
N1—C4	1.492 (2)	C21—C26	1.3962 (19)
N1—C7	1.5036 (18)	C22—H22	0.95
N2—C5	1.4718 (17)	C22—C23	1.395 (3)
N2—C6	1.4682 (19)	C23—H23	0.95
N2—C8	1.4848 (17)	C23—C24	1.383 (2)
C1—H1a	0.95	C24—H24	0.95
C1—C2	1.317 (2)	C24—C25	1.375 (3)
C1—C11	1.474 (2)	C25—H25	0.95
C2—H2	0.95	C25—C26	1.392 (2)
C2—C3	1.494 (2)	C26—H26	0.95
C3—H3a	0.99	C31—C32	1.393 (2)
C3—H3b	0.99	C31—C36	1.3867 (19)
H3a—H3b	1.5869	C32—H32	0.95
C4—H4a	0.99	C32—C33	1.389 (2)
C4—H4b	0.99	C33—H33	0.95
C4—C5	1.511 (2)	C33—C34	1.370 (2)
H4a—H4b	1.6058	C34—H34	0.95
C5—H5a	0.99	C34—C35	1.386 (3)
C5—H5b	0.99	C35—H35	0.95
H5a—H5b	1.6091	C35—C36	1.387 (2)
C6—H6a	0.99	C36—H36	0.95
C6—H6b	0.99	O1—C41	1.2810 (17)
C6—C7	1.512 (2)	O2—N3	1.2281 (18)
H6a—H6b	1.6016	O3—N3	1.215 (2)
C7—H7a	0.99	O4—N4	1.227 (2)
C7—H7b	0.99	O5—N4	1.224 (2)
H7a—H7b	1.6014	O6—C9	1.201 (2)
C8—H8	1	O7—C9	1.319 (2)
C8—C21	1.522 (2)	O7—H7	0.9238 (15)
C8—C31	1.5282 (19)	N3—C46	1.456 (2)
C11—C12	1.396 (2)	N4—C44	1.453 (2)
C11—C16	1.399 (3)	C9—C42	1.512 (3)
C12—H12	0.95	C41—C42	1.444 (2)
C12—C13	1.390 (2)	C41—C46	1.430 (2)
C13—H13	0.95	C42—C43	1.367 (2)
C13—C14	1.372 (3)	C43—H43	0.95
C14—H14	0.95	C43—C44	1.379 (2)
C14—C15	1.382 (3)	C44—C45	1.378 (2)
C15—H15	0.95	C45—H45	0.95
C15—C16	1.390 (3)	C45—C46	1.380 (2)

H71—N1—C3	109.70 (10)	C15—C16—H16	119.61
H71—N1—C4	107.37 (11)	C8—C21—C22	118.95 (12)
H71—N1—C7	106.90 (11)	C8—C21—C26	122.30 (13)
C3—N1—C4	112.27 (12)	C22—C21—C26	118.75 (14)
C3—N1—C7	110.59 (11)	C21—C22—H22	119.72
C4—N1—C7	109.82 (10)	C21—C22—C23	120.56 (14)
C5—N2—C6	107.42 (10)	H22—C22—C23	119.72
C5—N2—C8	110.41 (11)	C22—C23—H23	119.9
C6—N2—C8	110.71 (11)	C22—C23—C24	120.20 (16)
H1a—C1—C2	116.52	H23—C23—C24	119.9
H1a—C1—C11	116.52	C23—C24—H24	120.2
C2—C1—C11	126.96 (14)	C23—C24—C25	119.60 (17)
C1—C2—H2	118.03	H24—C24—C25	120.2
C1—C2—C3	123.95 (13)	C24—C25—H25	119.64
H2—C2—C3	118.03	C24—C25—C26	120.72 (15)
N1—C3—C2	112.26 (13)	H25—C25—C26	119.64
N1—C3—H3a	109.47	C21—C26—C25	120.16 (14)
N1—C3—H3b	109.47	C21—C26—H26	119.92
C2—C3—H3a	109.47	C25—C26—H26	119.92
C2—C3—H3b	109.47	C8—C31—C32	119.98 (11)
H3a—C3—H3b	106.54	C8—C31—C36	121.61 (13)
N1—C4—H4a	109.47	C32—C31—C36	118.41 (13)
N1—C4—H4b	109.47	C31—C32—H32	119.64
N1—C4—C5	110.53 (12)	C31—C32—C33	120.73 (13)
H4a—C4—H4b	108.39	H32—C32—C33	119.64
H4a—C4—C5	109.47	C32—C33—H33	119.85
H4b—C4—C5	109.47	C32—C33—C34	120.30 (16)
N2—C5—C4	110.21 (12)	H33—C33—C34	119.85
N2—C5—H5a	109.47	C33—C34—H34	120.18
N2—C5—H5b	109.47	C33—C34—C35	119.65 (15)
C4—C5—H5a	109.47	H34—C34—C35	120.18
C4—C5—H5b	109.47	C34—C35—H35	119.87
H5a—C5—H5b	108.72	C34—C35—C36	120.25 (14)
N2—C6—H6a	109.47	H35—C35—C36	119.88
N2—C6—H6b	109.47	C31—C36—C35	120.65 (15)
N2—C6—C7	110.93 (12)	C31—C36—H36	119.67
H6a—C6—H6b	107.97	C35—C36—H36	119.68
H6a—C6—C7	109.47	C41—O1—H7	101.64 (10)
H6b—C6—C7	109.47	C9—O7—H7	112.68 (16)
N1—C7—C6	110.95 (12)	O2—N3—O3	123.16 (15)
N1—C7—H7a	109.47	O2—N3—C46	118.72 (15)
N1—C7—H7b	109.47	O3—N3—C46	118.10 (13)
C6—C7—H7a	109.47	O4—N4—O5	122.91 (15)
C6—C7—H7b	109.47	O4—N4—C44	118.79 (14)
H7a—C7—H7b	107.95	O5—N4—C44	118.29 (16)
N2—C8—H8	108.39	O6—C9—O7	122.64 (19)
N2—C8—C21	111.04 (11)	O6—C9—C42	122.44 (16)
N2—C8—C31	110.45 (11)	O7—C9—C42	114.91 (15)
H8—C8—C21	107.41	O1—C41—C42	120.00 (15)
H8—C8—C31	108.03	O1—C41—C46	125.00 (14)
C21—C8—C31	111.38 (10)	C42—C41—C46	115.00 (13)
C1—C11—C12	122.33 (15)	C9—C42—C41	121.64 (14)
C1—C11—C16	119.24 (13)	C9—C42—C43	116.80 (14)
C12—C11—C16	118.42 (15)	C41—C42—C43	121.55 (16)
C11—C12—H12	119.81	C42—C43—H43	119.87
C11—C12—C13	120.37 (17)	C42—C43—C44	120.27 (14)
H12—C12—C13	119.81	H43—C43—C44	119.87
C12—C13—H13	119.82	N4—C44—C43	120.01 (14)
C12—C13—C14	120.37 (17)	N4—C44—C45	118.40 (15)
H13—C13—C14	119.82	C43—C44—C45	121.59 (13)
C13—C14—H14	119.8	C44—C45—H45	120.57
C13—C14—C15	120.40 (18)	C44—C45—C46	118.86 (15)
H14—C14—C15	119.8	H45—C45—C46	120.57
C14—C15—H15	120.17	N3—C46—C41	120.55 (13)
C14—C15—C16	119.7 (2)	N3—C46—C45	116.73 (14)
H15—C15—C16	120.17	C41—C46—C45	122.71 (13)
C11—C16—C15	120.77 (16)	O1—H7—O7	148.96 (9)
C11—C16—H16	119.61

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H71···O1ⁱ	0.9448 (11)	1.9544 (11)	2.8126 (15)	150.01 (8)
N1—H71···O2ⁱ	0.9448 (11)	2.3020 (16)	3.032 (2)	133.62 (8)
C3—H3a···O6ⁱⁱ	0.99	2.40	3.340 (2)	159
C5—H5a···C21	0.99	2.47	2.8777 (19)	104
C6—H6b···C31	0.99	2.50	2.8974 (19)	104
O7—H7···O1	0.9238 (15)	1.6675 (13)	2.505 (2)	148.96 (9)
O7—H7···C41	0.9238 (15)	2.2985 (16)	2.827 (2)	115.91 (9)

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

Overview of the redetermined structures top

REFCODE	Chemical name original/corrected if necessary
DUJZAK^a	Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate
JEVNAA^b	Tetrakis(1H-imidazole-N³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate / tetrakis(1H-imidazole-N³)zinc(II) bis(2-carboxy-4,6-dinitrophenolate)
LUDFUL^c	1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / phenazine 2-hydroxy-3,5-dinitrobenzoic acid
NUQVEB^d	2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) / 2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate) (0.38)/ 2-Amino-5-methylpyridinium 2-carboxy-4,6-dinitrophenolate (0.62)
QIQJAD^e	3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide solvate / 3,5-dinitro-2-hydroxybenzoate (0.55) 2-carboxy-4,6-dinitrophenolate (0.45) N,N-dimethylformamide monosolvate / 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate
SAFGUD^f	Bis(1,10-phenanthroline-5,6-dione-2N,N')silver(I) 2-hydroxy-3,5-dinitrobenzoate / Bis(1,10-phenanthroline-5,6-dione-2N,N')silver(I) 2-carboxy-4,6-dinitrophenolate
SEDKET^g	3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate / 3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate
TIYZIM^h	3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate
TUJPEVⁱ	4-[(5-methylisoxazol-3-yl)aminosulfonyl]anilinium 3,5-dinitrosalicylate
VABZIJ^j	2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolatemonohydrate
WADXOR^k	1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-hydroxy-3,5-dinitrobenzoate (0.73) / 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium 2-carboxy-4,6-2-carboxy-4,6-dinitrophenolate (0.37)
YAXPOE^l	4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate

Notes: (a) Zhang & Jian (2009); (b) Huang et al. (2007); (c) Senthil Kumar et al. (2002); (d) Hemamalini & Fun (2010a); (e) Sridhar et al. (2013); (f) Wang et al. (2012); (g) Wei et al. (2012); (h) Yamuna et al. (2014); (i) Malathy et al. (2015); (j) Hemamalini & Fun (2010b); (k) Smith & Lynch (2016); (l) Dayananda et al. (2012).

Hydrogen bonds (Å, °) in the redetermined structures top

D—H···A	D—H	H···A	D···A	D—H···A
DUJZAK
O1—H1aa···O8	0.759 (2)	1.859 (2)	2.606 (3)	167.96 (14)
	0.97 (4)	1.64 (4)	2.603 (3)	175 (3)
O2—H2aa···O9	0.922 (2)	1.727 (2)	2.631 (3)	166.48 (15)
	0.75 (4)	1.90 (4)	2.636 (3)	165 (4)
O3—H3b···O9	1.040 (2)	1.495 (2)	2.481 (3)	155.88 (12)
	1.11 (4)	1.41 (4)	2.480 (3)	160 (3)

JEVNAA
O2—H1a···O1	1.039 (2)	1.496 (2)	2.498 (2)	160.4 (1)
	0.89 (2)	1.65 (3)	2.503 (2)	160 (2)
N2—H2a···O3	0.967 (2)	1.890 (2)	2.838 (3)	165.9 (1)
	0.84 (2)	2.02 (2)	2.845 (3)	169 (2)
N4—H4a···O1ⁱ	0.943 (2)	1.924 (1)	2.784 (2)	150.6 (1)
	0.86 (2)	1.95 (2)	2.792 (2)	165 (2)

LUDFUL
O3—H3a···O2	1.059 (1)	1.530 (1)	2.513 (2)	151.7 (1)
	1.06 (2)	1.51 (2)	2.516 (2)	156 (2)
O1—H1a···N3	1.163 (1)	1.416 (1)	2.552 (2)	163.2 (1)
	1.14 (2)	1.44 (2)	2.552 (2)	166 (2)

NUQVEB
O7—H1o7···O1	0.919 (1)	1.531 (1)	2.4202 (12)	161.55 (6)
	1.14 (2)	1.31 (2)	2.4178 (12)	163 (2)
O1—H1o1···O7	0.931 (1)	1.513 (1)	2.4202 (12)	163.52 (6)
	1.31 (2)	1.14 (2)	2.4178 (12)	163 (2)
N2—H2a···O7ⁱⁱ	0.892 (1)	2.079 (1)	2.9655 (14)	172.84 (6)
	0.87 (1)	2.095 (14)	2.9674 (14)	176.5 (12)
N2—H2b···O1ⁱⁱⁱ	0.846 (1)	2.165 (1)	2.8526 (14)	138.40 (6)
	0.88 (2)	2.146 (14)	2.852 (1)	137.3 (11)
N2—H2b···O2ⁱⁱⁱ	0.846 (1)	2.413 (1)	3.1741 (14)	150.02 (6)
	0.88 (2)	2.384 (14)	3.1736 (15)	150.3 (11)
N1—H1···O6ⁱⁱ	0.898 (1)	1.783 (1)	2.6781 (13)	174.83 (6)
	0.90 (1)	1.784 (14)	2.6773 (14)	173.3 (13)

QIQJAD
N3—H3n···O2	0.862 (2)	1.994 (2)	2.854 (2)	174.8 (1)
	0.81 (3)	2.05 (3)	2.854 (3)	175 (3)
N3—H4n···O8^iv	0.863 (2)	2.059 (1)	2.921 (2)	176.9 (1)
	0.85 (2)	2.07 (2)	2.920 (2)	173 (3)
N2—H2n···O1	0.897 (2)	1.831 (2)	2.728 (2)	177.5 (1)
	0.81 (3)	1.93 (3)	2.731 (2)	171 (2)
N5—H5n···N4^v	0.866 (1)	2.141 (1)	2.9992 (19)	171.1 (1)
	0.84 (2)	2.17 (2)	2.999 (2)	171 (2)
N5—H6n···O8^vi	0.863 (2)	2.041 (2)	2.760 (2)	140.2 (1)
	0.78 (2)	2.12 (3)	2.764 (2)	141 (2)
O3—H3o···O1	0.926 (1)	1.562 (1)	2.4572 (18)	161.3 (1)
	0.99 (3)	1.49 (3)	2.4569 (19)	164 (3)

SAFGUD
O8—H7···O7	1.155 (4)	1.346 (4)	2.462 (6)	159.6 (3)
	1.05 (7)	1.57 (7)	2.452 (7)	138 (6)

SEDKET
O1—H2a···O2	1.22 (5)	1.34 (5)	2.476 (3)	149 (5)
	1.27 (3)	1.29 (3)	2.477 (3)	151 (3)
O2—H2a···O1	1.34 (5)	1.22 (5)	2.476 (3)	149 (5)
	1.29 (3)	1.27 (3)	2.477 (3)	151 (3)
N1—H1···O1^vii	1.11 (5)	1.92 (5)	2.799 (4)	133 (3)
	0.99 (4)	2.00 (3)	2.804 (4)	137 (3)
N1—H1···O7^vii	1.11 (5)	1.94 (5)	2.850 (4)	137 (3)
	0.99 (4)	2.03 (3)	2.855 (4)	140 (3)
N2—H2···O3	0.96 (3)	1.77 (3)	2.685 (4)	158 (3)
	0.99 (3)	1.75 (3)	2.684 (4)	157 (3)

TIYZIM
O2b—H2b···O1b	0.982 (1)	1.516 (1)	2.4473 (16)	156.3 (1)
	1.02 (2)	1.48 (2)	2.4476 (16)	156 (2)
N3a—H3aa···N1aa^viii	0.904 (1)	1.932 (1)	2.797 (2)	159.6 (1)
	0.91	1.92	2.797 (2)	162
N3a—H3ab···O2b^ix	0.901 (1)	2.565 (1)	3.1297 (17)	121.4 (1)
	0.91	2.58	3.1298 (17)	120
N3a—H3ab···O2b^ix	0.901 (1)	2.565 (1)	3.1297 (17)	121.4 (1)
	0.91	2.58	3.1297 (18)	120
N3a—H3ab···O3b^ix	0.901 (1)	2.072 (1)	2.9537 (17)	165.8 (1)
	0.91	2.06	2.9542 (17)	165
N3a—H3ac···O1b^x	0.893 (1)	2.061 (1)	2.815 (2)	141.5 (1)
	0.91	2.03	2.815 (2)	144
N3a—H3ac···O7b^x	0.893 (1)	2.484 (1)	2.9712 (19)	114.7 (1)
	0.91	2.46	2.9706 (19)	116

TUJPEV
O6—H6a···O5	1.184 (1)	1.295 (1)	2.4268 (16)	156.58 (6)
	1.24 (2)	1.21 (2)	2.4280 (17)	165.3 (14)
N1—H1a···O6^xi	1.002 (1)	2.068 (1)	3.0655 (17)	173.55 (7)
	0.89	2.24	3.0694 (17)	155
N1—H1b···N3^v	0.793 (1)	2.292 (1)	3.0393 (15)	157.3 (1)
	0.89	2.20	3.0382 (15)	157
N1—H1c···O4^v	0.832 (2)	1.831 (1)	2.663 (2)	177.1 (1)
	0.89	1.77	2.660 (2)	175
N2—H2a···O5	0.970 (1)	1.844 (1)	2.7852 (15)	162.64 (9)
	0.827 (17)	1.986 (16)	2.7900 (16)	164.0 (18)

VABZIJ
N3—H1n3···O6^x	0.973 (1)	1.754 (1)	2.7182 (14)	170.48 (8)
	0.91 (1)	1.823 (14)	2.7214 (14)	170.8 (15)
N4—H1n4···O1w	0.909 (1)	1.840 (1)	2.7348 (15)	167.76 (8)
	0.91 (2)	1.833 (15)	2.7323 (16)	172.0 (15)
O1w—H2w1···O1^xii	0.917 (1)	1.890 (1)	2.7886 (14)	166.21 (6)
	0.82 (2)	1.995 (19)	2.7906 (15)	162.7 (16)
O1w—H1w1—O3ⁱⁱⁱ	0.915 (1)	2.040 (1)	2.9352 (14)	165.84 (7)
	0.89 (2)	2.064 (18)	2.9357 (15)	168.0 (17)
O7—H7···O1	1.019 (1)	1.433 (1)	2.4340 (13)	165.94 (7)
	0.96 (2)	1.505 (16)	2.4358 (13)	162.0 (16)

WADXOR
N8a—H8a···O11b	0.960 (2)	1.933 (2)	2.864 (2)	162.83 (11)
	0.91 (2)	1.96 (2)	2.869 (2)	174.1 (17)
O11b—H21b···O21b	1.145 (2)	1.303 (6)	2.433 (6)	167.3 (3)
	1.07 (9)	1.48 (9)	2.430 (6)	145 (7)
O2b—H2b···O12b	1.103 (2)	1.385 (2)	2.471 (2)	166.81 (13)
	0.91 (3)	1.61 (3)	2.475 (3)	159 (3)

YAXPOE
N1—H71···O1^iv	0.945 (1)	1.954 (1)	2.813 (2)	150.01 (8)
	0.90 (2)	1.98 (2)	2.812 (2)	154.0 (19)
N1—H71···O2^iv	0.945 (1)	2.302 (2)	3.032 (2)	133.62 (8)
	0.90 (2)	2.36 (2)	3.034 (2)	131.8 (17)
O7—H7···O1	0.924 (2)	1.668 (1)	2.505 (2)	148.96 (9)
	0.92 (3)	1.71 (3)	2.504 (2)	142 (2)

Symmetry codes: (i) -x + 3/2, -y + 1/2, -z + 1; (ii) -x + 1, -y + 1, -z; (iii) -x + 1, -y, -z; (iv) -x + 1, -y + 1, -z + 1; (v) -x + 1, -y + 2, -z + 1; (vi) x - 1, y + 1, z; (vii) -x + 1, y + 1/2, -z + 1; (viii) -x, -y, -z; (ix) x + 1, y, z; (x) -x, -y + 1, -z + 1; (xi) -x, -y + 2, -z + 1; (xii) x, y + 1, z.

Overview of selected structures with different forms of the molecules: 2-hydroxy-3,5-dinitrobenzoic acid (I); 2-hydroxy-3,5-dinitrobenzoate (II); 2-carboxy-4,6-dinitrophenolate (III); 3,5-dinitro-2-oxidobenzoate (IV) top

The structures are ordered by ascending pKα value of the base. The corresponding values of (q1 + q2), D13, D1, D2 and D5 (cf. Fig. 1) are also given.

	Refcode	Base and its form present in the structure	pKα	ΔpKα	Type	(q1 + q2) (Å)	D13 (Å)	D1 (Å)	D2 (Å)	D5 (Å)	Remarks
1	GORXAM^a	1,4-dioxane	-3.9	-6.08	I	0.204 0.196	2.547 2.545	1.219 1.220	1.337 1.336	1.307 1.300	Two independent molecules
2	GORXEQ^a	1,4-dioxane	-3.9	-6.08	I	0.235	2.601	1.206	1.343	1.319
3	GORXEQ01^a	1,4-dioxane	-3.9	-6.08	I	0.197	2.531	1.222	1.346	1.302
4	AJEBOG^b	4-cyanopyridinium	1.92	-0.26	III	0.003	2.523	1.324	1.28	1.213
5	ABULAM^c	2-aminoanilinium	<2	<-0.18	III	0.011	2.447	1.309	1.282	1.219
6	PIDCAI^c	2-Aminoanilinium	<2	<-0.18	III	0.009	2.44	1.314	1.285	1.229	Wrongly attached hydrogen due to C═O distances. Originally determined as type II but it should be III.
7	PERBAR^d	3-carbamoylpyridinium	3.35	1.2	II	0.17	2.452	1.287	1.329	1.239	Wrongly attached hydrogen due to C═O distances. Originally determined as type II but it is probably III. Disorder present in the structure.
8	GIFMUE^e	1-naphthylammonium	3.92	1.74	III	0.011	2.488	1.31	1.279	1.224
9	MIPROS^f	8-aminoquinolinium	3.95	1.77	II	0.072	2.408	1.278	1.300	1.237	The bridging H is situated about the centre.
10	ABUKUF^g	4-chloroanilinium	3.98	1.80	II	0.094	2.435	1.276	1.297	1.242
11	YIVHIW^h	4-iodoanilinium	4.18	1.63	II	0.129	2.461	1.285	1.321	1.228
12	GIFNUFⁱ	1,10-phenanthrolinium	4.27	2.09	II	0.096	2.428	1.280	1.297	1.232	Determined as the type III but it is probably II (Fig. 1). The chemical name was correct.
13	FOXHAD^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	II	0.047	2.42	1.307	1.292	1.228	100 K; the reported hydrogen H3 is situated out of the plane formed by C···O bonds and is superficial.
14	KEZJIJ^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	III	0.07	2.422	1.293	1.296	1.231	C═O distances are about equal. The recalculation has shown that the bridging hydrogen is about the centre of the hydrogen bond, slightly closer to atom O2, which forms a shorter C═O bond.
15	KEZJIJ01^j	2-(pyridin-2-yl)pyridinium	4.33	2.15	III	0.066	2.423	1.295	1.299	1.221	C═O distances are about equal, the hydrogen is attached to the O atom forming a shorter C═O bond.
16	FICXIZ^k	cytosinium	4.60	2.42	II	0.098	2.423	1.285	1.310	1.234	The type according to the C═O distances should be II; the bridging hydrogen was wrongly attached.
17	ABUJUE^l	anilinium	4.60	2.42	II	0.129	2.448	1.280	1.323	1.231
18	ABUKOZ^m	4-fluoroanilinium	4.65	2.47	II	0.142	2.465	1.273	1.325	1.252
19	GIFMOYⁿ	quinolinium	4.85	2.67	III	0.05	2.414	1.294	1.285	1.235	The title molecule has similarly long C═O distances.
20	ZAJHAT^o	2-amminobenzoic acid	4.96	2.78	II	0.135	2.461	1.282	1.324	1.227
21	AJEBIA^p	pyridinium	5.23	3.05	I and II	0.142 0.163	2.458 2.582	1.250	1.308	1.257	Two independent molecules
22	EGABOF^q	2-methylquinolinium	5.71	3.53	II	0.285	2.411	1.207	1.359	1.244	outlier
23	AJECEX01^r	2,6-diaminopyridin-1-ium	6.13	3.95	II	0.072 0.121	2.435 2.464	1.298 1.295	1.309 1.332	1.241 1.237	One of the title molecules has similarly long C═O distances.
24	AJECIB^s	2-aminopyrimidinium	6.82	4.64	II	0.114 0.145	2.466 2.473	1.277 1.270	1.308 1.323	1.241 1.238
25	TUMWAB^t	1H-imidazol-3-ium	6.95	4.77	III	-0.01	2.457	1.320	1.279	1.214
26	LUMJOU^u	hydrazinium	8.12	5.94	III	0.014	2.459	1.318	1.275	1.211
27	SEDKET^v	3,5-dimethylpyrazolium	9	6.82	III	0.037	2.481	1.300	1.282	1.224
28	SEDKET^v (corrected)	3,5-dimethylpyrazolium	9	6.82	II	0.027	2.476	1.305	1.277	1.229	The bridging hydrogen after recalculation is closer to oxygen O1, which forms the shorter C═O bond (C12—O1).
29	LUDDET^w	benzylammonium	9.33	7.15	III	0.002	2.483	1.305	1.269	1.218
30	LUDDET01^w	benzylammonium	9.33	7.15	III			1.311 1.311	1.275 1.279	1.217 1.219
31	INELUI^x	1-phenylethylammonium	9.79	7.61	III	0.009 0.009	2.467 2.482	1.309 1.320	1.272 1.277	1.221 1.214
32	MILLOI^y	dicyclohexylammonium	10.4	8.22	III	0.028	2.464	1.289	1.273	1.225	The C═O distances of the title molecule are similar.
33	ACIFAT^z	4-sulfamoylanilinium	10.6	8.42	III	0.028	2.462	1.315	1.287	1.209
34	EGUTIJ^aa	methylammonium	10.6	8.42	III	0.011	2.481	1.314	1.276	1.218
35	EGUTOP^bb	triethylammonium	10.78	8.6	II	0.082	2.429	1.275	1.286	1.248
36	EGUTOP01^bb	triethylammonium	10.78	8.6	II	0.072	2.419	1.275	1.288	1.242
37	FOGZIL^cc	diethylammonium	11.09	8.91	III	0.004	2.489	1.308	1.270	1.217
38	XEBFAM^dd	piperidinium C₅H₁₁N	11.28	9.1	II and IV	0.078 0.061	2.586 2.736	1.219 1.234	1.278 1.253	1.255 1.271	One molecule of DNSA (I) is fully ionized, the other is in form II.
39	YEJZAO^ee	guanidinium	12.5	10.32	II	0.079	2.415	1.291	1.305	1.235
40	YEJZAO01^ee	guanidinium	12.5	10.32	II	0.073	2.415	1.292	1.300	1.239

References for the pKα values: (a) https://chemaxon.com/products/calculators-and-predictors\hashpka; (b) https://www.chemicalbook.com/ProductMSDSDetailCB0688145_EN.htm; (c) Dean (1987); (d) https://pubchem.ncbi.nlm.nih.gov/compound/nicotinamide\hashsection=pKa; (e) https://labs.chem.ucsb.edu/zhang/liming/pdf/pKas_of_Organic_Acids_and_Bases.pdf; (f) https://binarystore.wiley.com/store/10.1002/jcc.23068/asset/supinfo/JCC_23068_sm_SuppInfo.pdf?v=1&s=e864a51d58b4cdc175f6b69c92ceddb546201e3b; (g) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (h) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (i) https://chemicalland21.com/specialtychem/finechem/1,10-PHENANTHROLINE.htm; (j) https://www.chemicalbook.com/ProductMSDSDetailCB5195697_EN.htm; (k) https://www.drugfuture.com/chemdata/cytosine.html; (l) https://pubchem.ncbi.nlm.nih.gov/compound/aniline\hashsection=pKa; (m) https://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (n) Hosmane & Liebman (2009); (o) https://www.csun.edu/\~hcchm003/321/Ka.pdf; (p) https://pubchem.ncbi.nlm.nih.gov/compound/pyridine\hashsection=Dissociation-Constants; (q) https://onlinelibrary.wiley.com/doi/pdf/10.1002/jcc.23068; (r) https://www.chemicalbook.com/ProductMSDSDetailCB0236195_EN.htm; (s) https://pubchem.ncbi.nlm.nih.gov/compound/2-aminopyridine\hashsection=Dissociation-Constants; (t) https://pubchem.ncbi.nlm.nih.gov/compound/imidazole\hashsection=pKa; (u) https://evans.rc.fas.harvard.edu/pdf/evans_pKa_table.pdf; (v) https://www.chemicalbook.com/ProductMSDSDetailCB2707394_EN.htm; (w) https://pubchem.ncbi.nlm.nih.gov/compound/benzylamine\hashsection=pKa; (x) https://www.drugbank.ca/drugs/DB04325; (z) https://pubchem.ncbi.nlm.nih.gov/compound/dicyclohexylamine\hashsection=Dissociation-Constants; (z) https://pubchem.ncbi.nlm.nih.gov/compound/sulfanilamide\hashsection=Dissociation-Constants; (aa) https://pubchem.ncbi.nlm.nih.gov/compound/methylamine\hashsection=pKa; (ab) https://pubchem.ncbi.nlm.nih.gov/compound/triethylamine\hashsection=Dissociation-Constants; (ac) https://pubchem.ncbi.nlm.nih.gov/compound/diethylamine\hashsection=Dissociation-Constants; (ad) https://pubchem.ncbi.nlm.nih.gov/compound/piperidine\hashsection=Dissociation-Constants; (ae) https://pubchem.ncbi.nlm.nih.gov/compound/guanidine\hashsection=pKa.

References to publications with the chemical names of the determined compounds (original and corrected ones if necessary): (1) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (1:1)]; (2) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (3) Senthil Kumar et al. (1999): 3,5-dinitrosalicylic acid 1,4-dioxane solvate, 3,5-dinitrosalicylic acid 1,4-dioxane (2:1); (4) Smith et al. (2003a): 4-cyanopyridinium 3,5-dinitrosalicylate, 4-cyanopyridinium 3,5-dinitrosalicylate 2-carboxy-4,6-dinitrophenolate; (5) Smith et al. (2011): 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (6) Khan et al. (2013): 2-aminoanilinium 2-hydroxy-3,5-dinitrobenzoate, 2-aminoanilinium 2-carboxy-4,6-dinitrophenolate; (7) Jin et al. (2013): 3-carbamoylpyridinium 2-carboxy-4,6-dinitrophenolate, 3-carbamoylpyridinium 2-hydroxy-3,5-dinitrobenzoate; (8) Healy & White (2007): 1-naphthylammonium 3,5-dinitrosalicylate, 1-naphthylammonium 2-carboxy-4,6-dinitrophenolate; (9) Smith et al. (2001b): 8-aminoquinolinium 3,5-dinitrosalicylate; (10) Smith et al. (2011): 4-chloroanilinium 2-hydroxy-3,5-dinitrobenzoate; (11) Jones et al. (2014): (4-iodoanilinium 2-hydroxy-3,5-dinitrobenzoate; (12) Smith et al. (2007): 1,10-Phenanthrolinium 3,5-dinitrosalicylate; (13) Singh et al. (2014): 2-(pyridin-2-yl)pyridinium 2-hydroxy-3,5-dinitrobenzoate; (14) Song et al. (2007): 2,2'-bipyridinium 2-carboxy-4,6-dinitrophenolate; (15) Smith et al. (2007): 2,2'-bipyridinium 2-carboxy-4,6-dinitrophenolate; (16) Smith et al. (2005a): cytosinium 3,5-dinitrosalicylate, cytosinium 2-carboxy-4,6-dinitrophenolate; (17) Smith et al. (2011): anilinium 2-hydroxy-3,5-dinitrobenzoate; (18) Smith et al. (2011): 4-fluoroanilinium 2-hydroxy-3,5-dinitrobenzoate; (19) Smith, et al. (2007): quinolinium 3,5-dinitrosalicylate, quinolinium 2-carboxy-4,6-dinitrophenolate; (20) Smith et al. (1995): 3,5-dinitrosalicylic acid 2-aminobenzoic acid, 2-ammoniumbenzoic acid 2-carboxy-4,6-dinitrophenolate; (21) Smith et al. (2003b): pyridinium 3,5-dinitrosalicylate 3,5-dinitrosalicylic acid; (22) Zhang et al. (2014): 2-methylquinolinium 2-hydroxy-3,5-dinitrobenzoate; (23) Gao et al. (2015): 2,6-diaminopyridin-1-ium 2-hydroxy-3,5-dinitrobenzoate; (24) Smith et al. (2003a): 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol solvate, 2-aminopyrimidinium 3,5-dinitrosalicylate ethanol (2:2:1); (25) Jin et al. (2015b): 1H-imidazol-3-ium 2-carboxy-4,6-dinitrophenolate; (26) Fu et al. (2015): hydrazinium 2-carboxy-4,6-dinitrophenolate; (27) Wei et al. (2012): (3,5-Dimethylpyrazolium 2-carboxy-4,6-dinitrophenolate); (28) this work: (3,5-dimethylpyrazolium 2-hydroxy-3,5-dinitrobenzoate; (29) Smith et al. (2002b): benzylammonium 3,5-dinitrosalicylate, benzylammonium 2-carboxy-4,6-dinitrophenolate; (30) Jin et al. (2015a): benzylammonium 2-carboxy-4,6-dinitrophenolate; (31) Smith, Wermuth & White (2003): (S)-(-)-1-phenylethylaminium 3,5-dinitrosalicylate, (S)-(-)-1-phenylethylaminium 2-carboxy-4,6-dinitrophenolate; (32) Ng et al. (2001): dicyclohexylammonium 2-carboxy-4,6-dinitrophenolate; (33) Smith et al. (2001c): 4-ammoniobenzenesulfonamide 3,5-dinitrosalicylate, 4-ammoniobenzenesulfonamide 2-carboxy-4,6-dinitrophenolate; (34) Smith et al. (2002a): methylammonium 3,5-dinitrosalicylate, methylammonium 2-carboxy-4,6-dinitrophenolate; (35) Smith et al. (2002a): triethylammonium 3,5-dinitrosalicylate; (36) Rajkumar & Chandramohan (2017): triethylammonium 2-hydroxy-3,5-dinitrobenzoate; (37) Smith et al. (2005b): diethylammonium 3,5-dinitrosalicylate, diethylammonium 2-carboxy-4,6-dinitrophenolate; (38) Smith et al. (2006): tris(piperidinium) bis(3,5-dinitrosalicylate) monohydrate, tris(piperidinium) 2-hydroxy-3,5-dinitrobenzoate 2-olate-3,5-dinitrobenzoate monohydrate; (39) Smith et al. (2001a): guanidinium 3,5-dinitrosalicylate; (40) Fu et al. (2015): guanidinium 3,5-dinitrosalicylate.

Funding information

The author expresses gratitude for the support provided by Project NPU I – LO1603 of the Ministry of Education of the Czech Republic to the Institute of Physics of the Academy of Sciences of the Czech Republic.

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Volume 74| Part 9| September 2018| Pages 1344-1357

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

A resonance-assisted intra­molecular hydrogen bond in compounds containing 2-hy­dr­oxy-3,5-di­nitro­benzoic acid and its various deprotonated forms: redetermination of several related structures

1. Chemical context

2. Refinement of the title structures

3. Discussion of the inter­dependence of bond lengths and angles

4. Summary

Supporting information

Funding information

References

research communications

A resonance-assisted intramolecular hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms: redetermination of several related structures

3. Discussion of the interdependence of bond lengths and angles