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

A large number of structural determinations of compounds containing 2-hy­droxy-3,5-di­nitro­benzoic acid and its various deprotonated forms, 2-hy­droxy-3,5-di­nitro­benzoate or 2-carb­oxy-4,6-di­nitro­phenolate, 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. The present article examines the problem of the location and refinement of such a bridging hydrogen in a number of reported compounds. The analysis of the intra­molecular hydrogen bonding is also discussed.

Abstract

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.

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. 1 ▸ a. However, the delocalized bonds can be further extended within the mol­ecule, especially to the C=O/C—OH bond (D1/D5 in Fig. 1 ▸ a). 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. 2 ▸ a and 2 ▸ b 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
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
Δρmax, Δρmin (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	Monoclinic, P21/c	Monoclinic, P21	Triclinic, P
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
Δρmax, Δρmin (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	Triclinic, P	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[F 2 > 2σ(F 2)] = 0.046, wR(F 2) = 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
Δρmax, Δρmin (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
DUJZAKa	Bis(quinolin-8-ol)silver(I) 2-hy­droxy-3,5-di­nitro­benzoate
JEVNAAb	Tetra­kis(1H-imidazole-N 3)zinc(II) bis­(2-hy­droxy-3,5-di­nitro­benzoate / tetra­kis­(1H-imidazole-N 3)zinc(II) bis­(2-carb­oxy-4,6-di­nitro­phenolate)
LUDFULc	1-Aza-8-azoniabi­cyclo­[5.4.0]undec-7-ene 2-hy­droxy-3,5-di­nitro­benzoate / phenazine 2-hy­droxy-3,5-di­nitro­benzoic acid
NUQVEBd	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)
QIQJADe	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
SAFGUDf	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
SEDKETg	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
VABZIJj	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)
YAXPOEl	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.

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⋯O8iv	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⋯N4v	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⋯O8vi	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⋯O1vii	1.11 (5)	1.92 (5)	2.799 (4)	133 (3)
	0.99 (4)	2.00 (3)	2.804 (4)	137 (3)
N1—H1⋯O7vii	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⋯O6xi	1.002 (1)	2.068 (1)	3.0655 (17)	173.55 (7)
	0.89	2.24	3.0694 (17)	155
N1—H1b⋯N3v	0.793 (1)	2.292 (1)	3.0393 (15)	157.3 (1)
	0.89	2.20	3.0382 (15)	157
N1—H1c⋯O4v	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⋯O6x	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⋯O1xii	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⋯O1iv	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⋯O2iv	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 + , −y + , −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 + , −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—Hsp ² and C—H_meth­yl were constrained to equal to 0.93 and 0.96 Å, respectively. U _iso(Hsp ²) = 1.2U _eq(Csp ²) 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) + ΔI ²]^−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).

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. 1 ▸ a 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. 3 ▸ a 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. 3 ▸ b, 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.

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).

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	GORXEQa	1,4-dioxane	−3.9	−6.08	I	0.235	2.601	1.206	1.343	1.319
3	GORXEQ01a	1,4-dioxane	−3.9	−6.08	I	0.197	2.531	1.222	1.346	1.302
4	AJEBOGb	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	PIDCAIc	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	GIFMUEe	1-naphthylammonium	3.92	1.74	III	0.011	2.488	1.31	1.279	1.224
9	MIPROSf	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	ABUKUFg	4-chloroanilinium	3.98	1.80	II	0.094	2.435	1.276	1.297	1.242
11	YIVHIWh	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	FOXHADj	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	KEZJIJj	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	KEZJIJ01j	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	FICXIZk	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	ABUJUEl	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	ZAJHATo	2-amminobenzoic acid	4.96	2.78	II	0.135	2.461	1.282	1.324	1.227
21	AJEBIAp	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	EGABOFq	2-methylquinolinium	5.71	3.53	II	0.285	2.411	1.207	1.359	1.244	Outlier
23	AJECEX01r	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	AJECIBs	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	TUMWABt	1H-imidazol-3-ium	6.95	4.77	III	−0.01	2.457	1.320	1.279	1.214
26	LUMJOUu	hydrazinium	8.12	5.94	III	0.014	2.459	1.318	1.275	1.211
27	SEDKETv	3,5-di­methylpyrazolium	9	6.82	III	0.037	2.481	1.300	1.282	1.224
28	SEDKETv (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	LUDDETw	benzylammonium	9.33	7.15	III	0.002	2.483	1.305	1.269	1.218
30	LUDDET01w	benzylammonium	9.33	7.15	III			1.311 1.311	1.275 1.279	1.217 1.219
31	INELUIx	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	MILLOIy	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	ACIFATz	4-sulfamoylanilinium	10.6	8.42	III	0.028	2.462	1.315	1.287	1.209
34	EGUTIJaa	methylammonium	10.6	8.42	III	0.011	2.481	1.314	1.276	1.218
35	EGUTOPbb	tri­ethylammonium	10.78	8.6	II	0.082	2.429	1.275	1.286	1.248
36	EGUTOP01bb	tri­ethylammonium	10.78	8.6	II	0.072	2.419	1.275	1.288	1.242
37	FOGZILcc	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	YEJZAOee	guanidinium	12.5	10.32	II	0.079	2.415	1.291	1.305	1.235
40	YEJZAO01ee	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) http://binarystore.wiley.com/store/10.1002/jcc.23068/asset/supinfo/JCC_23068_sm_SuppInfo.pdf?v=1&s=e864a51d58b4cdc175f6b69c92ceddb546201e3b; (g) http://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (h) http://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (i) http://chemicalland21.com/specialtychem/finechem/1,10-PHENANTHROLINE.htm; (j) https://www.chemicalbook.com/ProductMSDSDetailCB5195697_EN.htm; (k) http://www.drugfuture.com/chemdata/cytosine.html; (l) https://pubchem.ncbi.nlm.nih.gov/compound/aniline#section=pKa; (m) http://sites.chem.colostate.edu/diverdi/all_courses/CRC%20reference%20data/dissociation%20constants%20of%20organic%20acids%20and%20bases.pdf; (n) Hosmane & Liebman (2009 ▸); (o) http://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) http://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.

Fig. 3 ▸ a 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. 3 ▸ c 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. 3 ▸ d compares both dependences shown in Figs. 3 ▸ a 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. 3 ▸ a–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. 3 ▸ e shows the same as Fig. 3 ▸ a 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. 4 ▸ a–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. 4 ▸ a) 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. 4 ▸ a) 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. 4 ▸ b), 1.43 Å (Fig. 4 ▸ c), 1.30 Å (Fig. 4 ▸ d), 1.37–1.39 Å (Fig. 4 ▸ e) and 1.41–1.43 Å (Fig. 4 ▸ f).

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. 5 ▸ a shows the dependence of D5 on (q1 + q2). Comparing Fig. 5 ▸ a to Fig. 4 ▸ a, 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. 5 ▸ a) is similar to that of bond D12 (Fig. 4 ▸ b) 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. 5 ▸ c and Fig. 4 ▸ d. Bond D7 is rather distant from the carb­oxy­lic group (Fig. 5 ▸ b) and the delocalization within the pyridine ring is no longer clear. The same holds for bonds D14 and D15 (Figs. 5 ▸ c and 5d). Figs. 5 ▸ e 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. 6 ▸ a–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. 1 ▸ b) shows once more the effect of incorrectly applied constraints, which are manifested by values close to 109.54° (cf. Figs. 2 ▸ a 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. 4 ▸ a 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. 1 ▸ a) should support the formation of a 2-carb­oxy-4,6-di­nitro­phenolate (III).

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 (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.

Supplementary Material

CCDC references: 1063245, 1862187, 1862188, 1862189, 1862190, 1862191, 1862192, 1862193, 1862194, 1862195, 1862196, 1862197, 1862198

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

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

[Ag(C9H7NO)2](C7H3N2O7)	F(000) = 628
Mr = 625.30	Dx = 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

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

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

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

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	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −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)

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

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

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.

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK). Atomic displacement parameters (Ų)

	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)

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK). Geometric parameters (Å, º)

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)

Bis(quinolin-8-ol)silver(I) 2-hydroxy-3,5-dinitrobenzoate (DUJZAK). Hydrogen-bond geometry (Å, º)

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) . Crystal data

[Zn(C3H4N2)4](C7H3N2O7)2	F(000) = 1616
Mr = 791.93	Dx = 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

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

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

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

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	Δρmax = 0.23 e Å−3
244 parameters	Δρmin = −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

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

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

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

Tetrakis(1H-imidazole-κN³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

Tetrakis(1H-imidazole-κN³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) . Atomic displacement parameters (Ų)

	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

Tetrakis(1H-imidazole-κN³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) . Geometric parameters (Å, º)

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)

Tetrakis(1H-imidazole-κN³)zinc(II) bis(2-hydroxy-3,5-dinitrobenzoate) (JEVNAA) . Hydrogen-bond geometry (Å, º)

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). Crystal data

C7H4N2O7·C12H8N2	Dx = 1.556 Mg m−3
Mr = 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

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.056
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 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%

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

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	Δρmax = 0.29 e Å−3
274 parameters	Δρmin = −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

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Special details

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

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

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Atomic displacement parameters (Ų)

	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)

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Geometric parameters (Å, º)

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)

3,5-Dinitrosalicylic acid–phenazine (1/1) (LUDFUL). Hydrogen-bond geometry (Å, º)

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). Crystal data

C6H9N2+·C7H3N2O7−	Z = 2
Mr = 336.27	F(000) = 348
Triclinic, P1	Dx = 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

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Data collection

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

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

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	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.32 e Å−3
34 constraints

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Special details

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

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	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)*

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Atomic displacement parameters (Ų)

	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)

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Geometric parameters (Å, º)

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)

2-Amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (NUQVEB). Hydrogen-bond geometry (Å, º)

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···O7iv	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···O6iv	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) . Crystal data

C9H8Cl2N5+·C7H3N2O7−·C3H7NO	Z = 2
Mr = 557.31	F(000) = 572
Triclinic, P1	Dx = 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

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

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

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

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	Δρmax = 0.80 e Å−3
48 constraints	Δρmin = −0.36 e Å−3

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

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

3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) . Atomic displacement parameters (Ų)

	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)

3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) . Geometric parameters (Å, º)

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)

3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazin-2-ium 3,5-dinitro-2-hydroxybenzoate N,N-dimethylformamide monosolvate (QIQJAD) . Hydrogen-bond geometry (Å, º)

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···O8iv	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) . Crystal data

[Ag(C12H6N2O2)](C7H3N2O7)	F(000) = 1512
Mr = 755.36	Dx = 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

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

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

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

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	Δρmax = 0.76 e Å−3
444 parameters	Δρmin = −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

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

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

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

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) . Atomic displacement parameters (Ų)

	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)

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) . Geometric parameters (Å, º)

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)

Bis(1,10-phenanthroline-5,6-dione-κ²N,N')silver(I) 3,5-dinitrosalicylate (SAFGUD) . Hydrogen-bond geometry (Å, º)

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). Crystal data

C5H9N2+·C7H3N2O7−	F(000) = 336
Mr = 324.26	Dx = 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

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Data collection

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

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Refinement

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	Δρmax = 0.11 e Å−3
2301 reflections	Δρmin = −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

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Special details

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. 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 10.

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Atomic displacement parameters (Ų)

	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)

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Geometric parameters (Å, º)

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

3,5-Dimethylpyrazolium 3,5-dinitrosalicylate (SEDKET). Hydrogen-bond geometry (Å, º)

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) . Crystal data

C6H12N3+·C7H3N2O7−	Z = 2
Mr = 353.30	F(000) = 368
Triclinic, P1	Dx = 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

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

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

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

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	Δρmax = 0.21 e Å−3
229 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
46 constraints	Extinction coefficient: 740 (130)

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

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

Refinement. Number of fixed parameters: 12

3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) . Atomic displacement parameters (Ų)

	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)

3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) . Geometric parameters (Å, º)

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)

3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate (TIYZIM) . Hydrogen-bond geometry (Å, º)

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···O1biv	0.8932 (14)	2.0610 (13)	2.815 (2)	141.47 (11)
N3a—H3ac···O7biv	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). Crystal data

C10H12N3O3S+·C7H3N2O7−	Z = 2
Mr = 481.41	F(000) = 496
Triclinic, P1	Dx = 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

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

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

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

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	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.35 e Å−3
48 constraints

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

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

4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV). Atomic displacement parameters (Ų)

	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)

4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV). Geometric parameters (Å, º)

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)

4-{[(5-Methylisoxazol-3-yl)amino]sulfonyl}anilinium 2-hydroxy-3,5-dinitrobenzoate (TUJPEV). Hydrogen-bond geometry (Å, º)

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). Crystal data

C8H13N2O+·C7H3N2O7−·H2O	Z = 2
Mr = 398.33	F(000) = 416
Triclinic, P1	Dx = 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

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

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

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

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	Δρmax = 0.46 e Å−3
52 constraints	Δρmin = −0.23 e Å−3

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

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

2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ). Atomic displacement parameters (Ų)

	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)

2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ). Geometric parameters (Å, º)

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)

2-Isopropyl-6-methyl-4-oxo-3,4-dihydropyrimidin-1-ium 2-carboxy-4,6-dinitrophenolate monohydrate (VABZIJ). Hydrogen-bond geometry (Å, º)

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). Crystal data

C9H17N2+·C7H3N2O7−	F(000) = 800
Mr = 380.35	Dx = 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

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

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	Rint = 0.034
ω scans	θmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −7→7
Tmin = 0.920, Tmax = 0.990	k = −23→23
7800 measured reflections	l = −17→17

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

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	Δρmax = 0.36 e Å−3
268 parameters	Δρmin = −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

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

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

1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	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)

1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR). Atomic displacement parameters (Ų)

	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)

1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR). Geometric parameters (Å, º)

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)

1-Aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate (WADXOR). Hydrogen-bond geometry (Å, º)

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···O21biv	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). Crystal data

C26H29N2+·C7H3N2O7−	F(000) = 1256
Mr = 596.63	Dx = 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

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

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

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

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	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.28 e Å−3
120 constraints

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

Refinement. Number of fixed parameters 6

4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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)*

4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE). Atomic displacement parameters (Ų)

	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)

4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE). Geometric parameters (Å, º)

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

4-(Diphenylmethyl)-1-(3-phenylprop-2-en-1-yl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (YAXPOE). Hydrogen-bond geometry (Å, º)

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.

Funding Statement

This work was funded by Ministerstvo Školství, Mládeže a Tělovýchovy grant NPU I – LO1603.