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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2022 Apr 26;78(Pt 5):510–518. doi: 10.1107/S2056989022004157

Crystal structures of six 4-(4-nitro­phenyl)­piperazin-1-ium salts

Ninganayaka Mahesha a, Haruvegowda Kiran Kumar a, Hemmige S Yathirajan a, Sabine Foro b, Mohammed S M Abdelbaky c, Santiago Garcia-Granda c,*
PMCID: PMC9069513  PMID: 35547797

Six piperazinium salts are reported, five of them are hydrated and two crystallized as 2:2 salts. They exhibit asymmetric units of a common 4-nitro­phenyl­piperazine cation and different p-substituent benzoate anions. Their crystal structures mainly pack as chains stabilized by strong N—H⋯O and O—H⋯O hydrogen bonds and other weak inter­actions such as C—H⋯O and C—H⋯π.

Keywords: crystal structure, piperazine, benzoate anion, biological activity

Abstract

Six piperazinium salts, namely 4-(4-nitro­phenyl)­piperazin-1-ium 4-bromo­ben­zo­ate dihydrate, C10H14N3O2 +·C7H4BrO2 ·2H2O, (I), 4-(4-nitro­phenyl)­pi­per­a­zin-1-ium 4-iodo­benzoate dihydrate, C10H14N3O2 +·C7H4IO2 ·2H2O, (II), 4-(4-nitro­phenyl)­piperazin-1-ium 4-hy­droxy­benzoate monohydrate, C10H14N3O2 +·C7H5O3 ·H2O, (III), 4-(4-nitro­phenyl)­piperazin-1-ium 4-methyl­benzoate monohydrate, C10H14N3O2 +·C8H7O2 ·H2O, (IV), 4-(4-nitro­phenyl)­piperazin-1-ium 4-meth­oxy­benzoate hemihydrate, 2C10H14N3O2 +·2C8H7O3 ·H2O, (V), and 4-(4-nitro­phenyl)­piperazin-1-ium 4-eth­oxy­benzoate, 2C10H14N3O2 +·2C9H9O3 , (VI), have been synthesized and their crystal structures solved by single-crystal X-ray diffraction, revealing that all of them crystallize in the triclinic space group P Inline graphic except for (V), which crystallizes in the monoclinic space group P21/c and has a disordered nitro group. Compounds (I) and (II) are isostructural. The crystal packing of (I)–(V) is constructed from organic chains formed by a combination of hydrogen bonds of type N—H⋯O and/or O—H⋯O and other weak inter­actions of type C—H⋯O and/or C—H⋯π, forming sheets, whereas (VI) shows a cationic and anionic-based layer structure.

1. Chemical context

Piperazines and substituted piperazines are important pharmacophores that can be found in many biologically active compounds used to treat a number of different diseases (Berkheij, 2005) as anti­fungal (Upadhayaya et al., 2004), anti-bacterial, anti-malarial and anti-psychotic agents (Choudhary et al., 2006). A valuable insight into advances on the anti­microbial activity of piperazine derivatives was given by Kharb et al. (2012). Piperazines are among the most important building blocks in current drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). Pharmacological and toxicological information for piperazine derivatives is reviewed by Elliott (2011).

4-Nitro­phenyl­piperazinium chloride monohydrate has been used as an inter­mediate in the synthesis of anti­cancer drugs, transcriptase inhibitors and anti­fungal reagents and is also an important reagent for potassium channel openers, which show considerable biomolecular current-voltage rectification characteristics (Lu, 2007). The inclusion behaviours of 4-sulf­on­ato­calix[n]arenes (SCXn) (n = 4, 6, 8) with 1-(4-nitrophen­yl)piperazine (NPP) were investigated by UV spectroscopy and fluorescence spectroscopy at different pH values (Zhang et al., 2014). The design, synthesis and biological profiling of aryl­piperazine-based scaffolds for the management of androgen-sensitive prostatic disorders was reported by Gupta et al. (2016). 4-Nitro­phenyl­piperazine was the starting material in the synthesis and biological evaluation of novel piperazine-containing hydrazone derivatives (Kaya et al., 2016). The crystal structure of 4-nitro­phenyl piperazinium chloride monohydrate was reported by Lu (2007) and that of 4,6-di­meth­oxy­pyrimidin-2-amine-1-(4-nitro­phen­yl)piperazine (1:1) by Wang et al. (2014) while Ayeni et al. (2019) described the synthesis and crystal structure of a Schiff base, 5-methyl-2-{[4-(4-nitro­phen­yl)piperazin-1-yl]meth­yl}phenol is published. NMR-based investigations of acyl-functionalized piperazines concerning their conformational behaviour in solution has been studied and the crystal structures of 1-(4-fluoro­benzo­yl)-4-(4-nitro­phen­yl)piperazine, 1-(4-bromo­benzo­yl)-4-(4-nitro­phen­yl)piperazine and 1-(3-bromo­benzo­yl)-4-(4-nitro­phen­yl)piperazine have been reported (Wodtke et al., 2018). We have recently reported the crystal structures of some salts of 4-meth­oxy­phenyl­piperazine (Kiran Kumar et al., 2019) and also 2-meth­oxy­phenyl­piperazine (Harish Chinthal et al., 2020), as well as some salts of piperazine derivatives (Archana et al., 2021). 1.

In view of the importance of piperazines in general and the use of 4-nitro­phenyl­piperazine in particular, the present paper reports the crystal structures of some salts of 4-nitro­phenyl­piperazine with organic acids. The crystal structures of 4-(4-nitro­phenyl)­piperazin-1-ium 4-bromo­benzoate dihydrate (I), 4-(4-nitro­phenyl)­piperazin-1-ium 4-iodo­benzoate dihydrate (II), 4-(4-nitro­phenyl)­piperazin-1-ium 4-hy­droxy­ben­zoate monohydrate (III), 4-(4-nitro­phenyl)­piperazin-1-ium 4-methyl­benzoate monohydrate (IV), 4-(4-nitro­phenyl)­pi­per­azin-1-ium 4-meth­oxy­benzoate hemihydrate (V) and 4-(4-nitro­phenyl)­piperazin-1-ium 4-eth­oxy­benzoate (VI) are reported herein.

2. Structural commentary

The asymmetric units of the title salts are shown in Figs. 1–6 . They include 1:1 dihydrated salts [(I), (II)], 1:1 monohydrated salts [(III), (IV)], 2:2 monohydrated salt (V) and solvent-free 2:2 salt (VI). Compounds (I) and (II) are isostructural. In all salts, the cation is common and consists of a protonated chair-shaped piperazine ring (N1/N2/C7–C10), which makes dihedral angles of 10.91 (1), 12.13 (1), 14.82 (6), 3.11 (8), 5.73 (1) and 13.08 (9)°, respectively, for compounds (I)–(VI) with the nitro­benzene moiety (N3/O1/O2/C1–C6) and exhibits a maximum deviation from its mean plane at atom N2 of −0.253 (2), 0.254 (2), 0.288 (2), 0.278 (2), 0.241 (3) and 0.303 (3) Å in (I)–(VI), respectively. The piperazine rings of the additional cations (N4/N5/C25–C28) in compounds (V) and (VI) have the same conformation, making dihedral angles of 64.53 (1) and 21.70 (1)°, respectively, with the nitro­benzene moieties (N6/O6/O7/C19–C25). Within the cations, the benzene rings are almost planar, with maximum deviations from mean plane ranging from −0.016 (3) Å at atom C20 for (VI) to 0.003 (2) Å at atom C4 for (III). The p-nitro substituent groups deviate significantly from planes of the benzene rings in all compounds except the (C1–C6) ring of (VI). The anions of the title salts are formed from a benzoate anion with different p-substituents for each compound that deviate significantly from planarity, with maximum deviations of 0.045 (1) Å at Br1 for (I), 0.063 (1) Å at I1 for (II), −0.021 (2) Å at hydroxyl atom O3 for (III), −0.010 (1) Å at methyl atom C18 for (IV), −0.033 (1) and 0.034 (1) Å at meth­oxy atoms O5 and O10 for (V) and −0.025 (2) and −0.013 (2) Å at eth­oxy atoms O5 and O10 for (VI).

Figure 1.

Figure 1

The independent components of compound (I) showing the atom-labelling scheme and the hydrogen bonds, drawn as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2.

Figure 2

The independent components of compound (II) showing the atom-labelling scheme and the hydrogen bonds, drawn as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

Figure 3.

Figure 3

The independent components of compound (III) showing the atom-labelling scheme and the hydrogen bonds, drawn as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

Figure 4.

Figure 4

The independent components of compound (IV) showing the atom-labelling scheme and the hydrogen bonds, drawn as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

Figure 5.

Figure 5

The independent components of compound (V) showing the atom-labelling scheme and the hydrogen bonds, drawn as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.

Figure 6.

Figure 6

The independent components of compound (VI) showing the atom-labelling scheme Displacement ellipsoids are drawn at the 50% probability level.

3. Supra­molecular features

In the crystal structures of the two isomorphous salts (I) and (II), the ions are arranged in chains perpendicular to the a-axis direction. The water mol­ecules play an essential role in holding the chains together, forming complex sheets in the bc plane (Figs. 7 and 8, Tables 1 and 2). The cations and anions in (III) are linked through strong O—H⋯O and N—H⋯O hydrogen bonds, forming chains along the [011] direction (Fig. 9 a, Table 3). These chains are further linked via the water mol­ecules and C9—H9A⋯O3 inter­actions, generating a three-dimensional supra­molecular architecture along the a axis (Fig. 9 b). The structure of (IV) is constructed from double chains running along the [101] direction. Each chain is formed by linking the mol­ecules through a combination of N—H⋯O, O—H⋯O and C—H⋯O inter­actions (Fig. 10 a, Table 4); the resulting double chains are symmetrically related by an inversion center and are connected via N2—H21⋯O4 and C7—H7A⋯O4 inter­actions. These hydrated double chains are weakly linked into sheets lying in the bc plane by C—H⋯π (arene) inter­actions (Fig. 10 b). The supra­molecular assembly of compound (V), which has a disordered nitro group, is built up of N2—H22N⋯O11, O11—H11O⋯O4 and N5—H51⋯O9 hydrogen bonds linking the ions into organic chains running parallel to the [010] direction (Fig. 11 a, Table 5). The chains are further connected cooperatively through other inter­actions of type N—H⋯O, generating a multilayer network along the b-axis direction (Fig. 11 b). In compound (VI), a set of N—H⋯O, C—H⋯O and C—H⋯π inter­actions (Fig. 12 a, Table 6) link the mol­ecules into cationic and anionic layers running parallel to the b-axis direction and join these layer motifs, generating the complete mol­ecular structure along the a axis (Fig. 12 b).

Figure 7.

Figure 7

(a) A general view of the main inter­molecular inter­actions (N—H⋯O and O—H⋯O) and (b) the mol­ecular packing of (I) with hydrogen bonds shown as dashed lines.

Figure 8.

Figure 8

(a) A general view of the main inter­molecular inter­actions (N—H⋯O and O—H⋯O) in (II) and (b) the mol­ecular packing of (II) with hydrogen bonds shown as dashed lines.

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

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O5i 0.85 (2) 1.99 (2) 2.810 (3) 162 (3)
N2—H22⋯O6ii 0.83 (2) 1.91 (2) 2.707 (3) 160 (3)
C3—H3⋯O1iii 0.93 2.59 3.260 (4) 130
C13—H13⋯O4iv 0.93 2.57 3.483 (3) 166
C15—H15⋯O2v 0.93 2.47 3.269 (4) 144
O5—H1W⋯O3vi 0.80 (2) 1.97 (2) 2.759 (2) 169 (3)
O5—H2W⋯O3i 0.80 (2) 2.00 (2) 2.772 (2) 161 (3)
O6—H4W⋯O4 0.82 (2) 2.03 (2) 2.832 (3) 166 (3)
O6—H3W⋯O4vii 0.78 (2) 1.99 (2) 2.760 (3) 169 (3)

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic ; (iv) Inline graphic ; (v) Inline graphic ; (vi) Inline graphic ; (vii) Inline graphic .

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

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O5i 0.86 (2) 1.99 (2) 2.825 (4) 164 (4)
N2—H22⋯O6ii 0.85 (2) 1.88 (2) 2.702 (3) 163 (4)
C3—H3⋯O1iii 0.93 2.59 3.275 (4) 131
C13—H13⋯O4iv 0.93 2.62 3.526 (4) 166
C15—H15⋯O2v 0.93 2.49 3.311 (4) 147
O5—H1W⋯O3vi 0.81 (2) 1.96 (2) 2.756 (3) 170 (4)
O5—H2W⋯O3i 0.81 (2) 1.96 (2) 2.753 (3) 166 (4)
O6—H4W⋯O4 0.80 (2) 2.08 (2) 2.836 (3) 160 (4)
O6—H3W⋯O4vii 0.80 (2) 1.95 (2) 2.728 (3) 165 (4)

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic ; (iv) Inline graphic ; (v) Inline graphic ; (vi) Inline graphic ; (vii) Inline graphic .

Figure 9.

Figure 9

(a) A general view of the main inter­molecular inter­actions (N—H⋯O and O—H⋯O) in (III) and (b) the mol­ecular packing of (III) with hydrogen bonds shown as dashed lines.

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

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O5 0.89 (2) 1.93 (2) 2.819 (2) 177 (3)
N2—H22⋯O4i 0.94 (2) 1.65 (2) 2.583 (2) 177 (3)
O3—H17⋯O6 0.85 (2) 1.82 (2) 2.669 (2) 177 (3)
O6—H1W⋯O5ii 0.83 (2) 1.95 (2) 2.768 (2) 169 (3)
O6—H2W⋯O1iii 0.83 (2) 2.11 (2) 2.944 (2) 178 (3)

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic .

Figure 10.

Figure 10

(a) A general view of the main inter­molecular inter­actions (N—H⋯O and O—H⋯O) in (IV) and (b) the mol­ecular packing of (IV) with hydrogen bonds shown as dashed lines.

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

Cg3 is the centroids of the C11–C16 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H21⋯O4i 0.89 (2) 1.93 (2) 2.811 (3) 167 (4)
N2—H22⋯O3ii 0.91 (2) 1.81 (2) 2.717 (3) 177 (4)
C3—H3⋯O1iii 0.93 2.54 3.427 (4) 161
C9—H9A⋯O5iv 0.97 2.31 3.113 (3) 140
O5—H1W⋯O4i 0.84 (2) 1.92 (2) 2.756 (3) 171 (4)
O5—H2W⋯O3 0.85 (2) 1.94 (2) 2.772 (3) 164 (4)
C6—H6⋯Cg3v 0.93 2.93 3.590 (3) 129

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic ; (iv) Inline graphic ; (v) Inline graphic .

Figure 11.

Figure 11

(a) A general view of the main inter­molecular inter­actions (N—H⋯O and O—H⋯O) in (V) and (b) the mol­ecular packing of (V) with hydrogen bonds shown as dashed lines.

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

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7B⋯O7i 0.97 2.54 3.451 (5) 157
C9—H9B⋯O4ii 0.97 2.31 3.270 (5) 169
C20—H20⋯O9 0.93 2.53 3.461 (5) 174
C25—H25A⋯O2aiii 0.97 2.5 3.206 (10) 130
C25—H25A⋯O2′biii 0.97 2.49 3.212 (11) 131
C27—H27A⋯O7i 0.97 2.58 3.548 (5) 175
C28—H28B⋯O9 0.97 2.55 3.489 (5) 164
C36—H36C⋯O1′bii 0.96 2.49 3.395 (14) 158
N2—H21N⋯O8iv 0.88 (2) 1.83 (2) 2.697 (4) 166 (4)
N2—H21N⋯O9iv 0.88 (2) 2.57 (3) 3.196 (4) 129 (3)
N2—H22N⋯O11v 0.88 (2) 1.89 (2) 2.758 (5) 169 (4)
N5—H51N⋯O9vi 0.87 (2) 1.93 (2) 2.778 (5) 164 (4)
N5—H52N⋯O3vii 0.91 (2) 1.82 (2) 2.724 (5) 171 (4)
O11—H11O⋯O4 0.84 (2) 1.83 (2) 2.663 (4) 176 (4)
O11—H12O⋯O8v 0.84 (2) 1.92 (2) 2.754 (4) 173 (4)

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic ; (iv) Inline graphic ; (v) Inline graphic ; (vi) Inline graphic ; (vii) Inline graphic .

Figure 12.

Figure 12

(a) A general view of the main inter­molecular inter­actions (N—H⋯O, O—H⋯O and C—H⋯O) in (VI) and (b) the mol­ecular packing of (VI) with hydrogen bonds shown as dashed lines.

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

Cg2 and Cg6 are the centroids of the C1–C6 and C30–C35 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H31N⋯O3i 0.94 (2) 1.68 (2) 2.613 (3) 172 (5)
N2—H31N⋯O4i 0.94 (2) 2.51 (4) 3.157 (3) 127 (4)
N2—H32N⋯O9ii 0.90 (2) 1.96 (2) 2.843 (3) 171 (5)
N5—H61N⋯O8i 0.91 (2) 1.78 (2) 2.686 (3) 175 (5)
N5—H61N⋯O9i 0.91 (2) 2.59 (4) 3.174 (3) 122 (4)
N5—H62N⋯O4iii 0.90 (2) 1.83 (2) 2.708 (3) 165 (5)
C22—H22⋯O2iv 0.93 2.6 3.502 (5) 165
C27—H27B⋯O9i 0.97 2.59 3.215 (3) 123
C28—H28B⋯O7v 0.97 2.65 3.410 (4) 135
C29—H29B⋯O1i 0.97 2.53 3.249 (4) 131
C35—H35⋯O4iii 0.93 2.52 3.263 (3) 137
C10—H10ACg6 0.97 2.82 3.746 (3) 159
C29—H29ACg2 0.97 2.76 3.556 (3) 139

Symmetry codes: (i) Inline graphic ; (ii) Inline graphic ; (iii) Inline graphic ; (iv) Inline graphic ; (v) Inline graphic .

4. Database survey

A search of the Cambridge Structural Database (Version 2020.3, last update February 2022; Groom et al., 2016) for the phenyl piperazinium cation and para substituent benzoate anion involved in the reported six salts gave the following hits, 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-fluoro­benzoate mono­hydrate, 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-chloro­benzoate monohydrate and 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-bromo­benzoate monohydrate (FOVPOY, FOVPUE and FOVQAL; Kiran Kumar et al., 2019) and 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-iodo­benzoate monohydrate (KUJ­PUD; Kiran Kumar et al., 2020). They exhibit a meth­oxy group as a substituent in the phenyl piperazinium cation rather than a nitro group as in the title compounds (I)–(VI) and they also crystallize as monohydrates similar to compounds (III)–(V). Although the title compounds (I) and (II) have halogen-based anions and chain-based structures, they are not isostructural with the above compounds, the crystal structures of which are based on differently sized chains of rings formed via a combination of hydrogen bonds of type N—H⋯O and O—H⋯O and other weak inter­actions of type C—H⋯O and C—H⋯π to form sheets. In 4-(4-meth­oxy­phen­yl)piperazin-1-ium 4-amino­benzoate monohydrate (IHIMEU; Kiran Kumar et al., 2020) the presence of an amino substituent on the anion, which acts as both a donor and an acceptor of hydrogen bonds, makes the supra­molecular assembly of this compound more complex than for the compounds reported herein.

5. Synthesis and crystallization

Synthesis:

For the synthesis of salts (I)–(VI), a solution of commercially available (from Sigma–Aldrich) 4-nitro­phenyl­piperazine (100 mg, 0.483 mol) in methanol (10 ml) was mixed with equimolar solutions of the appropriate acids in methanol (10 ml) and ethyl acetate (10 ml), viz.4-bromo­benzoic acid (97 mg, 0.483 mol) for (I), 4-iodo­benzoic acid (120 mg, 0.483 mol) for (II), 4-hy­droxy­benzoic acid (67 mg, 0.483 mol) for (III), 4-methyl­benzoic acid (66 mg, 0.483 mol) for (IV), 4-meth­oxy­benzoic acid (73 mg, 0.483 mol) for (V) and 4-eth­oxy­benzoic­acid (80 mg, 0.483 mol) for (VI). The corres­ponding solutions were stirred for 15 minutes at room temperature and allowed to stand at the same temperature. The products obtained were subjected to crystallization.

Crystallization: Crystallization was carried out using the slow evaporation technique. X-ray quality crystals were formed on slow evaporation in a week for all compounds, where ethanol:ethyl­acetate (1:1) was used for crystallization. The corresponding melting points were 430–432 K (I), 453–455 K (II), 446–448 K (III), 398–400 K (IV), 413–415 K (V) and 408–410 K (VI).

6. Refinement

Crystal data, data collection and refinement details are summarized in Table 7. C-bound H atoms were positioned with idealized geometry and refined using a riding model with C—H = 0.93 Å (aromatic), 0.96 Å (meth­yl) or 0.97 Å (methyl­ene). The H atoms on the N atom were located in a difference map and later restrained to N—H = 0.86 (2) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 U eq (C-aromatic, C-methyl­ene, N) or 1.5 U eq (C-meth­yl) times those of the parent atom. For the disordered nitro group in (V), the component atoms were restrained to have the same Uij components and the occupancy ratio is 0.519 (6):0.481 (6).

Table 7. Experimental details.

  (I) (II) (III)
Crystal data
Chemical formula C10H14N3O2 +·C7H4BrO2 ·2H2O C10H14N3O2 +·C7H4IO2 ·2H2O C10H14N3O2 +·C7H5O3 ·H2O
M r 444.28 491.28 363.37
Crystal system, space group Triclinic, P Inline graphic Triclinic, P Inline graphic Triclinic, P Inline graphic
Temperature (K) 293 293 293
a, b, c (Å) 7.738 (1), 9.320 (1), 13.949 (2) 7.7652 (4), 9.2852 (5), 13.930 (1) 9.636 (1), 10.301 (1), 10.867 (1)
α, β, γ (°) 94.46 (1), 95.04 (1), 104.71 (2) 94.985 (5), 95.331 (5), 104.875 (6) 103.90 (1), 108.32 (1), 112.96 (1)
V3) 964.0 (2) 960.09 (10) 857.80 (17)
Z 2 2 2
Radiation type Mo Kα Mo Kα Mo Kα
μ (mm−1) 2.17 1.71 0.11
Crystal size (mm) 0.48 × 0.44 × 0.24 0.48 × 0.48 × 0.2 0.50 × 0.32 × 0.24
 
Data collection
Diffractometer Oxford Diffraction Xcalibur Oxford Diffraction Xcalibur Oxford Diffraction Xcalibur
Absorption correction Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T min, T max 0.367, 0.422 0.458, 0.711 0.959, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections 6123, 3536, 2520 6331, 3518, 2952 5342, 3140, 2342
R int 0.019 0.017 0.013
(sin θ/λ)max−1) 0.602 0.602 0.602
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.037, 0.104, 1.04 0.029, 0.069, 1.03 0.043, 0.106, 1.05
No. of reflections 3528 3513 3135
No. of parameters 262 262 251
No. of restraints 6 6 5
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
Δρmax, Δρmin (e Å−3) 0.50, −0.51 0.54, −0.66 0.19, −0.19
  (IV) (V) (VI)
Crystal data
Chemical formula C10H14N3O2 +·C8H7O2 ·H2O 2C10H14N3O2 +·2C8H7O3 ·H2O C10H14N3O2 +·C9H9O3
M r 361.39 736.77 373.4
Crystal system, space group Triclinic, P Inline graphic Monoclinic, P21/c Triclinic, P Inline graphic
Temperature (K) 293 293 293
a, b, c (Å) 6.1136 (5), 7.6965 (7), 19.708 (2) 15.808 (1), 7.5198 (7), 31.020 (2) 7.874 (1), 9.263 (1), 27.996 (3)
α, β, γ (°) 79.577 (8), 87.162 (8), 86.699 (8) 90, 92.561 (7), 90 81.030 (6), 85.675 (6), 68.229 (5)
V3) 909.79 (15) 3683.8 (5) 1872.8 (4)
Z 2 4 4
Radiation type Mo Kα Mo Kα Mo Kα
μ (mm−1) 0.10 0.1 0.10
Crystal size (mm) 0.48 × 0.26 × 0.02 0.5 × 0.36 × 0.36 0.44 × 0.32 × 0.08
 
Data collection
Diffractometer Oxford Diffraction Xcalibur Oxford Diffraction Xcalibur Oxford Diffraction Xcalibur
Absorption correction Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T min, T max 0.970, 0.998 0.958, 0.965 0.963, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections 5980, 3347, 1911 15326, 6718, 2602 13344, 6868, 3803
R int 0.019 0.066 0.027
(sin θ/λ)max−1) 0.602 0.602 0.602
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.053, 0.138, 1.01 0.074, 0.169, 1.00 0.061, 0.137, 1.05
No. of reflections 3343 6715 6858
No. of parameters 248 507 501
No. of restraints 4 45 16
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
Δρmax, Δρmin (e Å−3) 0.20, −0.16 0.27, −0.18 0.23, −0.22

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXT (Sheldrick, 2015a ), Mercury (Macrae et al., 2020), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

Supplementary Material

Crystal structure: contains datablock(s) global, I, II, III, IV, V, VI. DOI: 10.1107/S2056989022004157/ex2056sup1.cif

e-78-00510-sup1.cif (2.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022004157/ex2056Isup2.hkl

e-78-00510-Isup2.hkl (281.4KB, hkl)

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989022004157/ex2056IIsup3.hkl

e-78-00510-IIsup3.hkl (280.3KB, hkl)

Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989022004157/ex2056IIIsup4.hkl

e-78-00510-IIIsup4.hkl (250.4KB, hkl)

Structure factors: contains datablock(s) IV. DOI: 10.1107/S2056989022004157/ex2056IVsup5.hkl

e-78-00510-IVsup5.hkl (266.8KB, hkl)

Structure factors: contains datablock(s) V. DOI: 10.1107/S2056989022004157/ex2056Vsup6.hkl

e-78-00510-Vsup6.hkl (533.7KB, hkl)

Structure factors: contains datablock(s) VI. DOI: 10.1107/S2056989022004157/ex2056VIsup7.hkl

e-78-00510-VIsup7.hkl (544.9KB, hkl)

CCDC references: 2167424, 2167423, 2167422, 2167421, 2167420, 2167419

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

supplementary crystallographic information

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Crystal data

C10H14N3O2+·C7H4BrO2·2H2O Z = 2
Mr = 444.28 F(000) = 456
Triclinic, P1 Dx = 1.531 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 7.738 (1) Å Cell parameters from 6123 reflections
b = 9.320 (1) Å θ = 3.0–25.3°
c = 13.949 (2) Å µ = 2.17 mm1
α = 94.46 (1)° T = 293 K
β = 95.04 (1)° Prism, yellow
γ = 104.71 (2)° 0.48 × 0.44 × 0.24 mm
V = 964.0 (2) Å3

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Data collection

Oxford Diffraction Xcalibur diffractometer 2520 reflections with I > 2σ(I)
ω scans Rint = 0.019
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.3°, θmin = 3.0°
Tmin = 0.367, Tmax = 0.422 h = −9→8
6123 measured reflections k = −6→11
3536 independent reflections l = −16→16

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.037 Hydrogen site location: mixed
wR(F2) = 0.104 H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0623P)2] where P = (Fo2 + 2Fc2)/3
3528 reflections (Δ/σ)max < 0.001
262 parameters Δρmax = 0.50 e Å3
6 restraints Δρmin = −0.51 e Å3
0 constraints

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.9273 (3) 0.7891 (3) 0.53814 (19) 0.0873 (8)
O2 0.6916 (3) 0.6357 (3) 0.57409 (17) 0.0767 (6)
N1 0.3360 (2) 1.0060 (2) 0.29246 (14) 0.0392 (5)
N2 0.1306 (3) 1.1025 (2) 0.13987 (16) 0.0433 (5)
N3 0.7641 (3) 0.7395 (3) 0.53118 (17) 0.0537 (6)
C1 0.4412 (3) 0.9374 (2) 0.34950 (16) 0.0353 (5)
C2 0.6297 (3) 0.9791 (3) 0.35426 (19) 0.0462 (6)
H2 0.685335 1.050743 0.316027 0.055*
C3 0.7335 (3) 0.9160 (3) 0.4144 (2) 0.0479 (6)
H3 0.858174 0.947226 0.418128 0.057*
C4 0.6524 (3) 0.8067 (3) 0.46921 (17) 0.0401 (6)
C5 0.4678 (3) 0.7621 (3) 0.46618 (18) 0.0460 (6)
H5 0.414057 0.688671 0.503722 0.055*
C6 0.3636 (3) 0.8264 (3) 0.40761 (18) 0.0430 (6)
H6 0.239197 0.796118 0.406198 0.052*
C7 0.4258 (3) 1.1047 (3) 0.2239 (2) 0.0479 (6)
H7A 0.454966 1.044787 0.17075 0.058*
H7B 0.537417 1.169773 0.256358 0.058*
C8 0.3088 (3) 1.1978 (3) 0.1846 (2) 0.0493 (7)
H8A 0.29158 1.266385 0.236558 0.059*
H8B 0.368224 1.256083 0.136469 0.059*
C9 0.0406 (3) 1.0114 (3) 0.2121 (2) 0.0495 (6)
H9A −0.074749 0.948618 0.182599 0.059*
H9B 0.01919 1.076165 0.265103 0.059*
C10 0.1561 (3) 0.9148 (3) 0.2506 (2) 0.0462 (6)
H10A 0.097528 0.858526 0.29974 0.055*
H10B 0.168666 0.844357 0.1984 0.055*
Br1 0.91659 (5) 0.45794 (4) 0.33416 (3) 0.08360 (18)
O3 0.4483 (2) 0.78822 (19) 0.01696 (15) 0.0543 (5)
O4 0.2197 (2) 0.63974 (18) 0.07787 (14) 0.0505 (5)
C11 0.5153 (3) 0.6356 (2) 0.13620 (18) 0.0350 (5)
C12 0.6851 (3) 0.6376 (3) 0.10986 (19) 0.0431 (6)
H12 0.71881 0.674975 0.052451 0.052*
C13 0.8046 (3) 0.5846 (3) 0.1680 (2) 0.0499 (7)
H13 0.916747 0.583844 0.149142 0.06*
C14 0.7551 (3) 0.5332 (3) 0.2538 (2) 0.0466 (6)
C15 0.5891 (3) 0.5325 (3) 0.28271 (19) 0.0459 (6)
H15 0.55828 0.499101 0.341588 0.055*
C16 0.4690 (3) 0.5821 (2) 0.22315 (19) 0.0424 (6)
H16 0.35572 0.579557 0.241532 0.051*
C17 0.3848 (3) 0.6919 (2) 0.07250 (19) 0.0391 (6)
O5 0.7579 (2) 0.01738 (19) 0.02770 (14) 0.0468 (4)
O6 0.0305 (3) 0.3352 (2) 0.06917 (16) 0.0581 (5)
H21 0.143 (4) 1.051 (3) 0.0892 (17) 0.07*
H22 0.075 (4) 1.160 (3) 0.118 (2) 0.07*
H1W 0.674 (3) −0.053 (3) 0.031 (2) 0.07*
H2W 0.720 (4) 0.088 (3) 0.018 (2) 0.07*
H4W 0.095 (4) 0.421 (2) 0.080 (2) 0.07*
H3W −0.041 (4) 0.331 (3) 0.0257 (18) 0.07*

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0490 (13) 0.0892 (16) 0.122 (2) 0.0142 (11) −0.0189 (13) 0.0497 (15)
O2 0.0701 (14) 0.0858 (15) 0.0809 (16) 0.0235 (12) −0.0004 (12) 0.0500 (13)
N1 0.0347 (10) 0.0406 (11) 0.0417 (11) 0.0091 (8) −0.0042 (9) 0.0124 (9)
N2 0.0459 (12) 0.0431 (12) 0.0435 (13) 0.0189 (10) −0.0065 (10) 0.0088 (10)
N3 0.0542 (15) 0.0524 (13) 0.0551 (14) 0.0173 (11) −0.0090 (12) 0.0161 (11)
C1 0.0396 (13) 0.0344 (12) 0.0327 (13) 0.0132 (10) −0.0010 (10) 0.0026 (10)
C2 0.0378 (14) 0.0518 (15) 0.0515 (16) 0.0111 (11) 0.0047 (12) 0.0229 (12)
C3 0.0361 (13) 0.0503 (15) 0.0583 (17) 0.0125 (11) −0.0001 (12) 0.0145 (13)
C4 0.0441 (14) 0.0411 (13) 0.0363 (13) 0.0156 (11) −0.0037 (11) 0.0060 (11)
C5 0.0489 (15) 0.0463 (14) 0.0429 (15) 0.0100 (11) 0.0016 (12) 0.0177 (11)
C6 0.0339 (12) 0.0498 (14) 0.0455 (15) 0.0093 (11) 0.0025 (11) 0.0145 (12)
C7 0.0416 (14) 0.0450 (14) 0.0524 (16) 0.0036 (11) −0.0082 (12) 0.0166 (12)
C8 0.0558 (16) 0.0385 (13) 0.0499 (16) 0.0096 (12) −0.0116 (13) 0.0117 (11)
C9 0.0392 (14) 0.0603 (16) 0.0517 (16) 0.0187 (12) −0.0040 (12) 0.0138 (13)
C10 0.0354 (13) 0.0487 (14) 0.0530 (16) 0.0077 (11) −0.0030 (12) 0.0159 (12)
Br1 0.0734 (3) 0.0942 (3) 0.0856 (3) 0.0319 (2) −0.02375 (19) 0.0272 (2)
O3 0.0418 (10) 0.0434 (10) 0.0808 (13) 0.0119 (8) 0.0005 (9) 0.0298 (9)
O4 0.0291 (9) 0.0497 (10) 0.0727 (13) 0.0090 (7) 0.0003 (8) 0.0169 (9)
C11 0.0330 (12) 0.0242 (11) 0.0468 (14) 0.0078 (9) −0.0007 (11) 0.0021 (10)
C12 0.0403 (14) 0.0432 (13) 0.0504 (16) 0.0160 (11) 0.0087 (12) 0.0125 (11)
C13 0.0345 (13) 0.0548 (15) 0.0659 (19) 0.0194 (11) 0.0057 (13) 0.0145 (14)
C14 0.0443 (15) 0.0381 (13) 0.0548 (17) 0.0096 (11) −0.0109 (13) 0.0102 (12)
C15 0.0500 (16) 0.0433 (14) 0.0403 (15) 0.0053 (11) −0.0007 (12) 0.0082 (11)
C16 0.0376 (13) 0.0378 (13) 0.0499 (16) 0.0068 (10) 0.0051 (12) 0.0034 (11)
C17 0.0375 (13) 0.0266 (11) 0.0533 (16) 0.0108 (10) −0.0010 (11) 0.0032 (11)
O5 0.0370 (10) 0.0413 (10) 0.0619 (12) 0.0103 (7) −0.0023 (9) 0.0133 (9)
O6 0.0491 (12) 0.0429 (10) 0.0816 (15) 0.0141 (8) −0.0142 (10) 0.0195 (10)

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Geometric parameters (Å, º)

O1—N3 1.222 (3) C8—H8B 0.97
O2—N3 1.217 (3) C9—C10 1.516 (3)
N1—C1 1.391 (3) C9—H9A 0.97
N1—C7 1.474 (3) C9—H9B 0.97
N1—C10 1.477 (3) C10—H10A 0.97
N2—C9 1.476 (4) C10—H10B 0.97
N2—C8 1.490 (3) Br1—C14 1.906 (2)
N2—H21 0.850 (17) O3—C17 1.264 (3)
N2—H22 0.833 (18) O4—C17 1.257 (3)
N3—C4 1.454 (3) C11—C16 1.388 (3)
C1—C2 1.405 (3) C11—C12 1.391 (3)
C1—C6 1.410 (3) C11—C17 1.506 (3)
C2—C3 1.376 (3) C12—C13 1.385 (3)
C2—H2 0.93 C12—H12 0.93
C3—C4 1.377 (4) C13—C14 1.374 (4)
C3—H3 0.93 C13—H13 0.93
C4—C5 1.378 (4) C14—C15 1.378 (4)
C5—C6 1.372 (3) C15—C16 1.382 (3)
C5—H5 0.93 C15—H15 0.93
C6—H6 0.93 C16—H16 0.93
C7—C8 1.502 (3) O5—H1W 0.802 (17)
C7—H7A 0.97 O5—H2W 0.802 (17)
C7—H7B 0.97 O6—H4W 0.823 (17)
C8—H8A 0.97 O6—H3W 0.778 (18)
C1—N1—C7 117.46 (19) N2—C8—H8B 109.4
C1—N1—C10 117.30 (18) C7—C8—H8B 109.4
C7—N1—C10 112.08 (19) H8A—C8—H8B 108
C9—N2—C8 109.8 (2) N2—C9—C10 110.3 (2)
C9—N2—H21 113 (2) N2—C9—H9A 109.6
C8—N2—H21 110 (2) C10—C9—H9A 109.6
C9—N2—H22 115 (2) N2—C9—H9B 109.6
C8—N2—H22 106 (2) C10—C9—H9B 109.6
H21—N2—H22 102 (3) H9A—C9—H9B 108.1
O2—N3—O1 122.4 (2) N1—C10—C9 111.3 (2)
O2—N3—C4 118.8 (2) N1—C10—H10A 109.4
O1—N3—C4 118.8 (2) C9—C10—H10A 109.4
N1—C1—C2 121.5 (2) N1—C10—H10B 109.4
N1—C1—C6 121.4 (2) C9—C10—H10B 109.4
C2—C1—C6 117.1 (2) H10A—C10—H10B 108
C3—C2—C1 121.2 (2) C16—C11—C12 118.6 (2)
C3—C2—H2 119.4 C16—C11—C17 120.5 (2)
C1—C2—H2 119.4 C12—C11—C17 120.9 (2)
C2—C3—C4 119.9 (2) C13—C12—C11 120.9 (2)
C2—C3—H3 120 C13—C12—H12 119.5
C4—C3—H3 120 C11—C12—H12 119.5
C3—C4—C5 120.6 (2) C14—C13—C12 119.0 (2)
C3—C4—N3 119.2 (2) C14—C13—H13 120.5
C5—C4—N3 120.2 (2) C12—C13—H13 120.5
C6—C5—C4 119.8 (2) C13—C14—C15 121.4 (2)
C6—C5—H5 120.1 C13—C14—Br1 119.7 (2)
C4—C5—H5 120.1 C15—C14—Br1 118.9 (2)
C5—C6—C1 121.4 (2) C14—C15—C16 119.2 (2)
C5—C6—H6 119.3 C14—C15—H15 120.4
C1—C6—H6 119.3 C16—C15—H15 120.4
N1—C7—C8 111.5 (2) C15—C16—C11 120.9 (2)
N1—C7—H7A 109.3 C15—C16—H16 119.6
C8—C7—H7A 109.3 C11—C16—H16 119.6
N1—C7—H7B 109.3 O4—C17—O3 124.3 (2)
C8—C7—H7B 109.3 O4—C17—C11 117.8 (2)
H7A—C7—H7B 108 O3—C17—C11 117.9 (2)
N2—C8—C7 111.17 (19) H1W—O5—H2W 108 (3)
N2—C8—H8A 109.4 H4W—O6—H3W 109 (3)
C7—C8—H8A 109.4
C7—N1—C1—C2 10.7 (3) C9—N2—C8—C7 58.1 (3)
C10—N1—C1—C2 148.9 (2) N1—C7—C8—N2 −55.1 (3)
C7—N1—C1—C6 −171.5 (2) C8—N2—C9—C10 −58.5 (3)
C10—N1—C1—C6 −33.3 (3) C1—N1—C10—C9 165.8 (2)
N1—C1—C2—C3 176.8 (2) C7—N1—C10—C9 −53.9 (3)
C6—C1—C2—C3 −1.1 (4) N2—C9—C10—N1 56.8 (3)
C1—C2—C3—C4 2.0 (4) C16—C11—C12—C13 1.3 (3)
C2—C3—C4—C5 −1.6 (4) C17—C11—C12—C13 −179.4 (2)
C2—C3—C4—N3 179.0 (2) C11—C12—C13—C14 −1.7 (4)
O2—N3—C4—C3 −174.9 (3) C12—C13—C14—C15 0.4 (4)
O1—N3—C4—C3 5.0 (4) C12—C13—C14—Br1 179.36 (19)
O2—N3—C4—C5 5.7 (4) C13—C14—C15—C16 1.2 (4)
O1—N3—C4—C5 −174.4 (3) Br1—C14—C15—C16 −177.75 (18)
C3—C4—C5—C6 0.5 (4) C14—C15—C16—C11 −1.6 (3)
N3—C4—C5—C6 179.9 (2) C12—C11—C16—C15 0.4 (3)
C4—C5—C6—C1 0.3 (4) C17—C11—C16—C15 −178.9 (2)
N1—C1—C6—C5 −177.9 (2) C16—C11—C17—O4 −26.9 (3)
C2—C1—C6—C5 0.0 (4) C12—C11—C17—O4 153.8 (2)
C1—N1—C7—C8 −166.7 (2) C16—C11—C17—O3 153.3 (2)
C10—N1—C7—C8 53.0 (3) C12—C11—C17—O3 −26.0 (3)

4-(4-Nitrophenyl)piperazin-1-ium 4-bromobenzoate dihydrate (I). Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2—H21···O5i 0.85 (2) 1.99 (2) 2.810 (3) 162 (3)
N2—H22···O6ii 0.83 (2) 1.91 (2) 2.707 (3) 160 (3)
C3—H3···O1iii 0.93 2.59 3.260 (4) 130
C13—H13···O4iv 0.93 2.57 3.483 (3) 166
C15—H15···O2v 0.93 2.47 3.269 (4) 144
O5—H1W···O3vi 0.80 (2) 1.97 (2) 2.759 (2) 169 (3)
O5—H2W···O3i 0.80 (2) 2.00 (2) 2.772 (2) 161 (3)
O6—H4W···O4 0.82 (2) 2.03 (2) 2.832 (3) 166 (3)
O6—H3W···O4vii 0.78 (2) 1.99 (2) 2.760 (3) 169 (3)

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

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Crystal data

C10H14N3O2+·C7H4IO2·2H2O Z = 2
Mr = 491.28 F(000) = 492
Triclinic, P1 Dx = 1.699 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 7.7652 (4) Å Cell parameters from 6331 reflections
b = 9.2852 (5) Å θ = 2.6–25.4°
c = 13.930 (1) Å µ = 1.71 mm1
α = 94.985 (5)° T = 293 K
β = 95.331 (5)° Prism, brown
γ = 104.875 (6)° 0.48 × 0.48 × 0.2 mm
V = 960.09 (10) Å3

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Data collection

Oxford Diffraction Xcalibur diffractometer 2952 reflections with I > 2σ(I)
ω scans Rint = 0.017
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.4°, θmin = 2.6°
Tmin = 0.458, Tmax = 0.711 h = −8→9
6331 measured reflections k = −11→9
3518 independent reflections l = −14→16

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Refinement

Refinement on F2 0 constraints
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.029 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0319P)2 + 0.5892P] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max < 0.001
3513 reflections Δρmax = 0.54 e Å3
262 parameters Δρmin = −0.66 e Å3
6 restraints

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.9211 (3) 0.7945 (3) 0.5327 (2) 0.0765 (8)
O2 0.6869 (3) 0.6415 (3) 0.5706 (2) 0.0702 (7)
N1 0.3324 (3) 1.0055 (2) 0.29012 (17) 0.0344 (5)
N2 0.1277 (3) 1.1016 (3) 0.13972 (19) 0.0404 (6)
N3 0.7583 (4) 0.7448 (3) 0.52680 (19) 0.0471 (6)
C1 0.4369 (3) 0.9384 (3) 0.34660 (19) 0.0311 (6)
C2 0.6239 (4) 0.9794 (3) 0.3495 (2) 0.0421 (7)
H2 0.678241 1.049839 0.310458 0.051*
C3 0.7273 (4) 0.9175 (3) 0.4087 (2) 0.0434 (7)
H3 0.851637 0.947138 0.411003 0.052*
C4 0.6475 (4) 0.8107 (3) 0.4653 (2) 0.0348 (6)
C5 0.4638 (4) 0.7665 (3) 0.4644 (2) 0.0407 (7)
H5 0.411197 0.694461 0.502907 0.049*
C6 0.3609 (4) 0.8297 (3) 0.4063 (2) 0.0390 (7)
H6 0.236893 0.800552 0.405831 0.047*
C7 0.4203 (4) 1.1048 (3) 0.2222 (2) 0.0412 (7)
H7A 0.448427 1.044706 0.168453 0.049*
H7B 0.532139 1.170403 0.255077 0.049*
C8 0.3038 (4) 1.1984 (3) 0.1836 (2) 0.0439 (7)
H8A 0.287569 1.267775 0.236 0.053*
H8B 0.361796 1.256375 0.135285 0.053*
C9 0.0381 (4) 1.0095 (4) 0.2115 (2) 0.0456 (7)
H9A −0.07676 0.945606 0.181239 0.055*
H9B 0.016429 1.074515 0.264773 0.055*
C10 0.1531 (4) 0.9144 (3) 0.2497 (2) 0.0413 (7)
H10A 0.096206 0.859686 0.299686 0.05*
H10B 0.163241 0.841846 0.19758 0.05*
I1 0.92211 (3) 0.44728 (3) 0.33815 (2) 0.05798 (10)
O3 0.4459 (3) 0.7894 (2) 0.01595 (18) 0.0503 (6)
O4 0.2183 (3) 0.6411 (2) 0.07685 (16) 0.0463 (5)
C11 0.5106 (3) 0.6368 (3) 0.1340 (2) 0.0321 (6)
C12 0.6798 (4) 0.6390 (3) 0.1072 (2) 0.0387 (7)
H12 0.71341 0.676998 0.050132 0.046*
C13 0.7975 (4) 0.5851 (3) 0.1648 (2) 0.0411 (7)
H13 0.909115 0.584052 0.146196 0.049*
C14 0.7470 (4) 0.5326 (3) 0.2509 (2) 0.0376 (7)
C15 0.5813 (4) 0.5331 (3) 0.2798 (2) 0.0398 (7)
H15 0.550434 0.499714 0.338523 0.048*
C16 0.4631 (4) 0.5834 (3) 0.2208 (2) 0.0378 (7)
H16 0.350345 0.581695 0.238875 0.045*
C17 0.3825 (4) 0.6931 (3) 0.0705 (2) 0.0356 (6)
O5 0.7577 (3) 0.0174 (2) 0.02906 (17) 0.0446 (5)
O6 0.0304 (3) 0.3341 (3) 0.06807 (19) 0.0529 (6)
H21 0.144 (5) 1.051 (4) 0.0882 (19) 0.063*
H22 0.076 (4) 1.162 (3) 0.116 (3) 0.063*
H1W 0.671 (4) −0.051 (3) 0.032 (3) 0.063*
H2W 0.711 (5) 0.084 (3) 0.022 (3) 0.063*
H4W 0.100 (4) 0.414 (3) 0.080 (3) 0.063*
H3W −0.052 (4) 0.326 (4) 0.027 (2) 0.063*

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0437 (15) 0.0752 (18) 0.108 (2) 0.0122 (13) −0.0192 (14) 0.0400 (16)
O2 0.0633 (16) 0.0754 (18) 0.0786 (18) 0.0200 (13) 0.0033 (13) 0.0469 (15)
N1 0.0300 (12) 0.0321 (13) 0.0391 (13) 0.0054 (10) −0.0037 (10) 0.0090 (10)
N2 0.0420 (14) 0.0388 (15) 0.0413 (15) 0.0159 (11) −0.0066 (12) 0.0072 (11)
N3 0.0496 (17) 0.0450 (16) 0.0461 (15) 0.0151 (13) −0.0076 (13) 0.0084 (13)
C1 0.0328 (14) 0.0280 (14) 0.0316 (14) 0.0093 (11) −0.0008 (11) 0.0009 (11)
C2 0.0340 (15) 0.0433 (17) 0.0496 (18) 0.0067 (13) 0.0047 (13) 0.0196 (14)
C3 0.0279 (15) 0.0464 (18) 0.0548 (19) 0.0086 (13) −0.0010 (13) 0.0115 (15)
C4 0.0369 (15) 0.0344 (15) 0.0332 (15) 0.0118 (12) −0.0029 (12) 0.0049 (12)
C5 0.0422 (17) 0.0417 (17) 0.0383 (16) 0.0087 (13) 0.0047 (13) 0.0139 (13)
C6 0.0292 (14) 0.0443 (17) 0.0430 (17) 0.0073 (12) 0.0016 (12) 0.0118 (13)
C7 0.0353 (15) 0.0389 (17) 0.0459 (17) 0.0034 (13) −0.0040 (13) 0.0148 (14)
C8 0.0483 (18) 0.0350 (16) 0.0447 (17) 0.0078 (14) −0.0075 (14) 0.0095 (13)
C9 0.0354 (16) 0.055 (2) 0.0479 (18) 0.0160 (14) −0.0023 (14) 0.0103 (15)
C10 0.0297 (15) 0.0401 (17) 0.0524 (18) 0.0071 (13) −0.0035 (13) 0.0110 (14)
I1 0.05063 (15) 0.06217 (17) 0.06139 (16) 0.01852 (11) −0.01269 (10) 0.01870 (11)
O3 0.0370 (11) 0.0400 (12) 0.0758 (16) 0.0088 (9) 0.0016 (11) 0.0276 (11)
O4 0.0283 (11) 0.0460 (12) 0.0629 (14) 0.0073 (9) −0.0016 (10) 0.0134 (10)
C11 0.0290 (14) 0.0241 (14) 0.0415 (16) 0.0059 (11) −0.0004 (12) 0.0023 (12)
C12 0.0376 (16) 0.0394 (16) 0.0431 (17) 0.0138 (13) 0.0088 (13) 0.0119 (13)
C13 0.0315 (15) 0.0436 (17) 0.0516 (19) 0.0157 (13) 0.0044 (13) 0.0082 (14)
C14 0.0336 (15) 0.0306 (15) 0.0458 (17) 0.0078 (12) −0.0064 (13) 0.0047 (13)
C15 0.0421 (17) 0.0365 (16) 0.0373 (16) 0.0043 (13) 0.0025 (13) 0.0068 (13)
C16 0.0288 (14) 0.0356 (16) 0.0471 (17) 0.0062 (12) 0.0048 (13) 0.0018 (13)
C17 0.0328 (15) 0.0241 (14) 0.0475 (17) 0.0073 (12) −0.0011 (13) −0.0012 (12)
O5 0.0345 (11) 0.0374 (13) 0.0610 (14) 0.0094 (9) −0.0027 (10) 0.0111 (11)
O6 0.0442 (13) 0.0383 (12) 0.0735 (17) 0.0097 (10) −0.0123 (11) 0.0164 (12)

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Geometric parameters (Å, º)

O1—N3 1.222 (3) C8—H8B 0.97
O2—N3 1.221 (3) C9—C10 1.503 (4)
N1—C1 1.376 (3) C9—H9A 0.97
N1—C10 1.462 (3) C9—H9B 0.97
N1—C7 1.469 (4) C10—H10A 0.97
N2—C8 1.473 (4) C10—H10B 0.97
N2—C9 1.479 (4) I1—C14 2.090 (3)
N2—H21 0.859 (18) O3—C17 1.257 (3)
N2—H22 0.850 (18) O4—C17 1.257 (3)
N3—C4 1.440 (4) C11—C16 1.391 (4)
C1—C2 1.400 (4) C11—C12 1.395 (4)
C1—C6 1.410 (4) C11—C17 1.493 (4)
C2—C3 1.361 (4) C12—C13 1.377 (4)
C2—H2 0.93 C12—H12 0.93
C3—C4 1.378 (4) C13—C14 1.386 (4)
C3—H3 0.93 C13—H13 0.93
C4—C5 1.378 (4) C14—C15 1.385 (4)
C5—C6 1.357 (4) C15—C16 1.372 (4)
C5—H5 0.93 C15—H15 0.93
C6—H6 0.93 C16—H16 0.93
C7—C8 1.502 (4) O5—H1W 0.805 (18)
C7—H7A 0.97 O5—H2W 0.805 (18)
C7—H7B 0.97 O6—H4W 0.795 (18)
C8—H8A 0.97 O6—H3W 0.800 (18)
C1—N1—C10 117.2 (2) N2—C8—H8B 109.6
C1—N1—C7 117.8 (2) C7—C8—H8B 109.6
C10—N1—C7 112.8 (2) H8A—C8—H8B 108.1
C8—N2—C9 110.6 (2) N2—C9—C10 110.3 (2)
C8—N2—H21 108 (3) N2—C9—H9A 109.6
C9—N2—H21 115 (3) C10—C9—H9A 109.6
C8—N2—H22 104 (3) N2—C9—H9B 109.6
C9—N2—H22 118 (3) C10—C9—H9B 109.6
H21—N2—H22 101 (3) H9A—C9—H9B 108.1
O2—N3—O1 122.5 (3) N1—C10—C9 111.5 (2)
O2—N3—C4 119.1 (3) N1—C10—H10A 109.3
O1—N3—C4 118.4 (3) C9—C10—H10A 109.3
N1—C1—C2 121.1 (2) N1—C10—H10B 109.3
N1—C1—C6 121.5 (2) C9—C10—H10B 109.3
C2—C1—C6 117.4 (2) H10A—C10—H10B 108
C3—C2—C1 120.9 (3) C16—C11—C12 119.5 (3)
C3—C2—H2 119.6 C16—C11—C17 120.4 (2)
C1—C2—H2 119.6 C12—C11—C17 120.1 (2)
C2—C3—C4 119.9 (3) C13—C12—C11 120.4 (3)
C2—C3—H3 120.1 C13—C12—H12 119.8
C4—C3—H3 120.1 C11—C12—H12 119.8
C5—C4—C3 121.2 (3) C12—C13—C14 119.0 (3)
C5—C4—N3 119.5 (3) C12—C13—H13 120.5
C3—C4—N3 119.3 (3) C14—C13—H13 120.5
C6—C5—C4 118.9 (3) C15—C14—C13 121.4 (3)
C6—C5—H5 120.5 C15—C14—I1 119.1 (2)
C4—C5—H5 120.5 C13—C14—I1 119.6 (2)
C5—C6—C1 121.8 (3) C16—C15—C14 119.2 (3)
C5—C6—H6 119.1 C16—C15—H15 120.4
C1—C6—H6 119.1 C14—C15—H15 120.4
N1—C7—C8 111.9 (2) C15—C16—C11 120.5 (3)
N1—C7—H7A 109.2 C15—C16—H16 119.8
C8—C7—H7A 109.2 C11—C16—H16 119.8
N1—C7—H7B 109.2 O4—C17—O3 125.0 (3)
C8—C7—H7B 109.2 O4—C17—C11 116.9 (2)
H7A—C7—H7B 107.9 O3—C17—C11 118.1 (2)
N2—C8—C7 110.2 (2) H1W—O5—H2W 101 (4)
N2—C8—H8A 109.6 H4W—O6—H3W 117 (4)
C7—C8—H8A 109.6
C10—N1—C1—C2 148.6 (3) C9—N2—C8—C7 58.1 (3)
C7—N1—C1—C2 8.9 (4) N1—C7—C8—N2 −54.7 (3)
C10—N1—C1—C6 −33.7 (4) C8—N2—C9—C10 −58.5 (3)
C7—N1—C1—C6 −173.4 (3) C1—N1—C10—C9 165.8 (3)
N1—C1—C2—C3 177.1 (3) C7—N1—C10—C9 −52.6 (3)
C6—C1—C2—C3 −0.8 (4) N2—C9—C10—N1 55.3 (4)
C1—C2—C3—C4 1.3 (5) C16—C11—C12—C13 1.6 (4)
C2—C3—C4—C5 −1.0 (5) C17—C11—C12—C13 −179.0 (3)
C2—C3—C4—N3 179.3 (3) C11—C12—C13—C14 −1.7 (4)
O2—N3—C4—C5 6.3 (4) C12—C13—C14—C15 0.1 (4)
O1—N3—C4—C5 −173.9 (3) C12—C13—C14—I1 179.0 (2)
O2—N3—C4—C3 −173.9 (3) C13—C14—C15—C16 1.6 (4)
O1—N3—C4—C3 5.8 (4) I1—C14—C15—C16 −177.4 (2)
C3—C4—C5—C6 0.1 (5) C14—C15—C16—C11 −1.6 (4)
N3—C4—C5—C6 179.8 (3) C12—C11—C16—C15 0.0 (4)
C4—C5—C6—C1 0.4 (5) C17—C11—C16—C15 −179.3 (3)
N1—C1—C6—C5 −178.0 (3) C16—C11—C17—O4 −26.0 (4)
C2—C1—C6—C5 −0.1 (4) C12—C11—C17—O4 154.6 (3)
C1—N1—C7—C8 −166.2 (2) C16—C11—C17—O3 153.1 (3)
C10—N1—C7—C8 52.5 (3) C12—C11—C17—O3 −26.2 (4)

4-(4-Nitrophenyl)piperazin-1-ium 4-iodobenzoate dihydrate (II). Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2—H21···O5i 0.86 (2) 1.99 (2) 2.825 (4) 164 (4)
N2—H22···O6ii 0.85 (2) 1.88 (2) 2.702 (3) 163 (4)
C3—H3···O1iii 0.93 2.59 3.275 (4) 131
C13—H13···O4iv 0.93 2.62 3.526 (4) 166
C15—H15···O2v 0.93 2.49 3.311 (4) 147
O5—H1W···O3vi 0.81 (2) 1.96 (2) 2.756 (3) 170 (4)
O5—H2W···O3i 0.81 (2) 1.96 (2) 2.753 (3) 166 (4)
O6—H4W···O4 0.80 (2) 2.08 (2) 2.836 (3) 160 (4)
O6—H3W···O4vii 0.80 (2) 1.95 (2) 2.728 (3) 165 (4)

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

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Crystal data

C10H14N3O2+·C7H5O3·H2O Z = 2
Mr = 363.37 F(000) = 384
Triclinic, P1 Dx = 1.407 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 9.636 (1) Å Cell parameters from 5342 reflections
b = 10.301 (1) Å θ = 2.6–25.3°
c = 10.867 (1) Å µ = 0.11 mm1
α = 103.90 (1)° T = 293 K
β = 108.32 (1)° Rod, yellow
γ = 112.96 (1)° 0.50 × 0.32 × 0.24 mm
V = 857.80 (17) Å3

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Data collection

Oxford Diffraction Xcalibur diffractometer 2342 reflections with I > 2σ(I)
ω scans Rint = 0.013
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.3°, θmin = 2.6°
Tmin = 0.959, Tmax = 0.974 h = −11→11
5342 measured reflections k = −12→11
3140 independent reflections l = −13→12

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Refinement

Refinement on F2 Hydrogen site location: mixed
Least-squares matrix: full H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0386P)2 + 0.3231P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106 (Δ/σ)max < 0.001
S = 1.05 Δρmax = 0.19 e Å3
3135 reflections Δρmin = −0.19 e Å3
251 parameters Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraints Extinction coefficient: 0.032 (3)
0 constraints

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.3138 (2) 0.37000 (19) 0.65529 (18) 0.0346 (4)
C2 0.1431 (2) 0.2527 (2) 0.57638 (19) 0.0418 (4)
H2 0.068235 0.250847 0.613904 0.05*
C3 0.0843 (2) 0.1407 (2) 0.4450 (2) 0.0434 (5)
H3 −0.029409 0.063818 0.39416 0.052*
C4 0.1942 (2) 0.1428 (2) 0.38907 (19) 0.0411 (4)
C5 0.3624 (2) 0.2553 (2) 0.4636 (2) 0.0483 (5)
H5 0.436252 0.255393 0.42532 0.058*
C6 0.4208 (2) 0.3670 (2) 0.5942 (2) 0.0472 (5)
H6 0.53484 0.443048 0.64379 0.057*
C7 0.5230 (2) 0.6338 (2) 0.8284 (2) 0.0453 (5)
H7A 0.489341 0.67826 0.763471 0.054*
H7B 0.611237 0.616548 0.817407 0.054*
C8 0.5933 (2) 0.7472 (2) 0.9784 (2) 0.0493 (5)
H8A 0.643572 0.71093 1.044494 0.059*
H8B 0.681545 0.846719 0.99504 0.059*
C9 0.3302 (3) 0.6143 (2) 0.9836 (2) 0.0457 (5)
H9A 0.242868 0.625614 1.002896 0.055*
H9B 0.381743 0.579404 1.050389 0.055*
C10 0.2514 (2) 0.4953 (2) 0.83370 (19) 0.0403 (4)
H10A 0.176601 0.394834 0.82667 0.048*
H10B 0.183115 0.521491 0.76885 0.048*
C11 0.1749 (2) 0.5843 (2) 0.29147 (19) 0.0418 (5)
C12 0.2469 (3) 0.7413 (2) 0.3258 (2) 0.0495 (5)
H12 0.262285 0.778209 0.258209 0.059*
C13 0.2959 (2) 0.8431 (2) 0.4597 (2) 0.0438 (5)
H13 0.344454 0.94863 0.481898 0.053*
C14 0.2738 (2) 0.7906 (2) 0.56226 (18) 0.0364 (4)
C15 0.2004 (2) 0.6329 (2) 0.52544 (19) 0.0395 (4)
H15 0.18337 0.595519 0.592378 0.047*
C16 0.1520 (2) 0.5299 (2) 0.39188 (19) 0.0410 (4)
H16 0.104259 0.424435 0.369591 0.049*
C17 0.3293 (2) 0.9024 (2) 0.7080 (2) 0.0440 (5)
N1 0.37669 (18) 0.48418 (16) 0.78933 (15) 0.0372 (4)
N2 0.4599 (2) 0.76559 (19) 1.00415 (18) 0.0479 (4)
N3 0.1322 (2) 0.02537 (19) 0.25010 (18) 0.0518 (4)
O1 0.2282 (2) 0.04014 (19) 0.19537 (17) 0.0759 (5)
O2 −0.0112 (2) −0.08579 (18) 0.19233 (16) 0.0715 (5)
O3 0.1311 (2) 0.48813 (18) 0.15852 (15) 0.0637 (4)
O4 0.3985 (2) 1.04290 (17) 0.73256 (16) 0.0744 (5)
O5 0.30323 (18) 0.85085 (16) 0.79750 (14) 0.0547 (4)
O6 −0.0679 (3) 0.1917 (2) 0.09903 (19) 0.0809 (6)
H21 0.412 (3) 0.796 (3) 0.941 (2) 0.097*
H22 0.513 (3) 0.838 (3) 1.099 (2) 0.097*
H17 0.070 (3) 0.394 (2) 0.143 (3) 0.097*
H1W −0.140 (3) 0.168 (3) 0.129 (3) 0.097*
H2W −0.112 (3) 0.128 (3) 0.015 (2) 0.097*

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0348 (10) 0.0343 (9) 0.0377 (10) 0.0187 (8) 0.0167 (8) 0.0173 (8)
C2 0.0357 (10) 0.0427 (10) 0.0444 (11) 0.0159 (8) 0.0211 (8) 0.0168 (9)
C3 0.0356 (10) 0.0380 (10) 0.0439 (11) 0.0113 (8) 0.0148 (8) 0.0145 (9)
C4 0.0463 (11) 0.0347 (9) 0.0373 (10) 0.0191 (8) 0.0175 (8) 0.0119 (8)
C5 0.0429 (11) 0.0481 (11) 0.0505 (12) 0.0215 (9) 0.0255 (9) 0.0120 (10)
C6 0.0315 (10) 0.0440 (11) 0.0514 (12) 0.0139 (8) 0.0177 (9) 0.0081 (9)
C7 0.0379 (10) 0.0401 (10) 0.0487 (11) 0.0133 (8) 0.0209 (9) 0.0137 (9)
C8 0.0459 (11) 0.0395 (11) 0.0468 (11) 0.0154 (9) 0.0160 (9) 0.0117 (9)
C9 0.0590 (12) 0.0451 (11) 0.0434 (11) 0.0277 (10) 0.0295 (10) 0.0231 (9)
C10 0.0429 (10) 0.0421 (10) 0.0420 (10) 0.0213 (9) 0.0239 (9) 0.0211 (9)
C11 0.0398 (10) 0.0443 (11) 0.0361 (10) 0.0170 (9) 0.0194 (8) 0.0133 (9)
C12 0.0595 (13) 0.0525 (12) 0.0441 (11) 0.0248 (10) 0.0315 (10) 0.0269 (10)
C13 0.0494 (11) 0.0392 (10) 0.0482 (11) 0.0207 (9) 0.0274 (9) 0.0224 (9)
C14 0.0357 (9) 0.0405 (10) 0.0381 (10) 0.0210 (8) 0.0190 (8) 0.0183 (8)
C15 0.0410 (10) 0.0440 (10) 0.0378 (10) 0.0201 (8) 0.0208 (8) 0.0223 (9)
C16 0.0409 (10) 0.0356 (10) 0.0423 (11) 0.0151 (8) 0.0194 (8) 0.0167 (8)
C17 0.0482 (11) 0.0462 (12) 0.0409 (11) 0.0255 (9) 0.0218 (9) 0.0180 (9)
N1 0.0349 (8) 0.0348 (8) 0.0385 (8) 0.0157 (7) 0.0170 (7) 0.0130 (7)
N2 0.0616 (11) 0.0410 (9) 0.0425 (10) 0.0259 (8) 0.0257 (9) 0.0168 (8)
N3 0.0575 (11) 0.0430 (10) 0.0443 (10) 0.0214 (9) 0.0209 (9) 0.0124 (8)
O1 0.0806 (12) 0.0662 (11) 0.0599 (10) 0.0220 (9) 0.0434 (9) 0.0052 (8)
O2 0.0600 (10) 0.0523 (9) 0.0564 (10) 0.0087 (8) 0.0163 (8) 0.0010 (8)
O3 0.0759 (11) 0.0545 (9) 0.0430 (8) 0.0171 (8) 0.0337 (8) 0.0121 (7)
O4 0.1147 (14) 0.0416 (9) 0.0554 (10) 0.0278 (9) 0.0450 (10) 0.0145 (7)
O5 0.0721 (10) 0.0620 (9) 0.0425 (8) 0.0375 (8) 0.0324 (7) 0.0259 (7)
O6 0.0936 (14) 0.0547 (10) 0.0652 (11) 0.0142 (10) 0.0484 (10) 0.0041 (8)

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Geometric parameters (Å, º)

C1—N1 1.392 (2) C10—H10A 0.97
C1—C6 1.397 (2) C10—H10B 0.97
C1—C2 1.402 (2) C11—O3 1.360 (2)
C2—C3 1.371 (3) C11—C16 1.379 (3)
C2—H2 0.93 C11—C12 1.382 (3)
C3—C4 1.373 (3) C12—C13 1.374 (3)
C3—H3 0.93 C12—H12 0.93
C4—C5 1.373 (3) C13—C14 1.389 (2)
C4—N3 1.446 (2) C13—H13 0.93
C5—C6 1.365 (3) C14—C15 1.383 (2)
C5—H5 0.93 C14—C17 1.494 (3)
C6—H6 0.93 C15—C16 1.378 (2)
C7—N1 1.468 (2) C15—H15 0.93
C7—C8 1.501 (3) C16—H16 0.93
C7—H7A 0.97 C17—O4 1.250 (2)
C7—H7B 0.97 C17—O5 1.260 (2)
C8—N2 1.470 (3) N2—H21 0.893 (17)
C8—H8A 0.97 N2—H22 0.935 (17)
C8—H8B 0.97 N3—O2 1.221 (2)
C9—N2 1.476 (2) N3—O1 1.230 (2)
C9—C10 1.507 (3) O3—H17 0.850 (17)
C9—H9A 0.97 O6—H1W 0.832 (17)
C9—H9B 0.97 O6—H2W 0.834 (17)
C10—N1 1.467 (2)
N1—C1—C6 120.65 (15) N1—C10—H10B 108.9
N1—C1—C2 122.40 (15) C9—C10—H10B 108.9
C6—C1—C2 116.95 (16) H10A—C10—H10B 107.8
C3—C2—C1 121.37 (17) O3—C11—C16 122.11 (17)
C3—C2—H2 119.3 O3—C11—C12 118.10 (17)
C1—C2—H2 119.3 C16—C11—C12 119.78 (17)
C2—C3—C4 119.60 (17) C13—C12—C11 120.14 (18)
C2—C3—H3 120.2 C13—C12—H12 119.9
C4—C3—H3 120.2 C11—C12—H12 119.9
C3—C4—C5 120.68 (17) C12—C13—C14 120.94 (17)
C3—C4—N3 119.73 (17) C12—C13—H13 119.5
C5—C4—N3 119.59 (17) C14—C13—H13 119.5
C6—C5—C4 119.67 (17) C15—C14—C13 118.02 (16)
C6—C5—H5 120.2 C15—C14—C17 121.42 (16)
C4—C5—H5 120.2 C13—C14—C17 120.55 (16)
C5—C6—C1 121.72 (17) C16—C15—C14 121.51 (17)
C5—C6—H6 119.1 C16—C15—H15 119.2
C1—C6—H6 119.1 C14—C15—H15 119.2
N1—C7—C8 113.07 (16) C15—C16—C11 119.60 (17)
N1—C7—H7A 109 C15—C16—H16 120.2
C8—C7—H7A 109 C11—C16—H16 120.2
N1—C7—H7B 109 O4—C17—O5 124.14 (18)
C8—C7—H7B 109 O4—C17—C14 116.82 (17)
H7A—C7—H7B 107.8 O5—C17—C14 119.04 (17)
N2—C8—C7 110.93 (16) C1—N1—C10 116.66 (14)
N2—C8—H8A 109.5 C1—N1—C7 115.79 (14)
C7—C8—H8A 109.5 C10—N1—C7 114.73 (14)
N2—C8—H8B 109.5 C8—N2—C9 108.67 (15)
C7—C8—H8B 109.5 C8—N2—H21 109.1 (18)
H8A—C8—H8B 108 C9—N2—H21 108.9 (18)
N2—C9—C10 110.96 (15) C8—N2—H22 106.2 (17)
N2—C9—H9A 109.4 C9—N2—H22 110.8 (17)
C10—C9—H9A 109.4 H21—N2—H22 113 (2)
N2—C9—H9B 109.4 O2—N3—O1 122.24 (17)
C10—C9—H9B 109.4 O2—N3—C4 119.43 (17)
H9A—C9—H9B 108 O1—N3—C4 118.32 (17)
N1—C10—C9 113.15 (15) C11—O3—H17 110.2 (19)
N1—C10—H10A 108.9 H1W—O6—H2W 108 (3)
C9—C10—H10A 108.9
N1—C1—C2—C3 −179.46 (17) O3—C11—C16—C15 179.34 (17)
C6—C1—C2—C3 −0.3 (3) C12—C11—C16—C15 0.4 (3)
C1—C2—C3—C4 0.0 (3) C15—C14—C17—O4 178.09 (18)
C2—C3—C4—C5 0.4 (3) C13—C14—C17—O4 −1.4 (3)
C2—C3—C4—N3 −179.58 (17) C15—C14—C17—O5 −2.4 (3)
C3—C4—C5—C6 −0.5 (3) C13—C14—C17—O5 178.03 (18)
N3—C4—C5—C6 179.41 (18) C6—C1—N1—C10 169.31 (17)
C4—C5—C6—C1 0.3 (3) C2—C1—N1—C10 −11.5 (2)
N1—C1—C6—C5 179.30 (18) C6—C1—N1—C7 29.6 (2)
C2—C1—C6—C5 0.1 (3) C2—C1—N1—C7 −151.19 (18)
N1—C7—C8—N2 −53.2 (2) C9—C10—N1—C1 176.12 (15)
N2—C9—C10—N1 52.1 (2) C9—C10—N1—C7 −43.8 (2)
O3—C11—C12—C13 −178.90 (18) C8—C7—N1—C1 −175.25 (16)
C16—C11—C12—C13 0.1 (3) C8—C7—N1—C10 44.3 (2)
C11—C12—C13—C14 −0.2 (3) C7—C8—N2—C9 61.2 (2)
C12—C13—C14—C15 −0.3 (3) C10—C9—N2—C8 −60.7 (2)
C12—C13—C14—C17 179.26 (18) C3—C4—N3—O2 −9.7 (3)
C13—C14—C15—C16 0.8 (3) C5—C4—N3—O2 170.3 (2)
C17—C14—C15—C16 −178.76 (17) C3—C4—N3—O1 171.61 (19)
C14—C15—C16—C11 −0.8 (3) C5—C4—N3—O1 −8.3 (3)

4-(4-Nitrophenyl)piperazin-1-ium 4-hydroxybenzoate monohydrate (III). Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
N2—H21···O5 0.89 (2) 1.93 (2) 2.819 (2) 177 (3)
N2—H22···O4i 0.94 (2) 1.65 (2) 2.583 (2) 177 (3)
O3—H17···O6 0.85 (2) 1.82 (2) 2.669 (2) 177 (3)
O6—H1W···O5ii 0.83 (2) 1.95 (2) 2.768 (2) 169 (3)
O6—H2W···O1iii 0.83 (2) 2.11 (2) 2.944 (2) 178 (3)

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

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Crystal data

C10H14N3O2+·C8H7O2·H2O Z = 2
Mr = 361.39 F(000) = 384
Triclinic, P1 Dx = 1.319 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 6.1136 (5) Å Cell parameters from 5980 reflections
b = 7.6965 (7) Å θ = 3.1–25.4°
c = 19.708 (2) Å µ = 0.10 mm1
α = 79.577 (8)° T = 293 K
β = 87.162 (8)° Plate, yellow
γ = 86.699 (8)° 0.48 × 0.26 × 0.02 mm
V = 909.79 (15) Å3

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Data collection

Oxford Diffraction Xcalibur diffractometer 1911 reflections with I > 2σ(I)
ω scans Rint = 0.019
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.4°, θmin = 3.1°
Tmin = 0.970, Tmax = 0.998 h = −5→7
5980 measured reflections k = −8→9
3347 independent reflections l = −23→21

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Refinement

Refinement on F2 0 constraints
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.053 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.2441P] where P = (Fo2 + 2Fc2)/3
S = 1.01 (Δ/σ)max < 0.001
3343 reflections Δρmax = 0.20 e Å3
248 parameters Δρmin = −0.16 e Å3
4 restraints

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.7597 (5) −0.1408 (4) 0.52918 (12) 0.1114 (9)
O2 1.0599 (5) −0.2808 (4) 0.50875 (13) 0.1312 (11)
N1 0.8270 (3) 0.0591 (2) 0.20408 (9) 0.0426 (5)
N2 0.8376 (3) 0.2441 (3) 0.06365 (10) 0.0492 (5)
N3 0.9029 (6) −0.1858 (4) 0.48992 (13) 0.0795 (8)
C1 0.8503 (4) 0.0072 (3) 0.27523 (12) 0.0421 (6)
C2 0.6848 (5) 0.0416 (4) 0.32264 (13) 0.0620 (8)
H2 0.559385 0.107832 0.306884 0.074*
C3 0.7020 (5) −0.0200 (4) 0.39241 (13) 0.0660 (8)
H3 0.58958 0.005008 0.423273 0.079*
C4 0.8844 (5) −0.1175 (4) 0.41582 (13) 0.0589 (7)
C5 1.0511 (5) −0.1516 (4) 0.37142 (15) 0.0698 (8)
H5 1.175889 −0.217226 0.388096 0.084*
C6 1.0361 (4) −0.0894 (4) 0.30170 (13) 0.0606 (8)
H6 1.152207 −0.112351 0.271761 0.073*
C7 0.6682 (4) 0.2049 (3) 0.18122 (12) 0.0490 (6)
H7A 0.721093 0.313511 0.191295 0.059*
H7B 0.530333 0.182601 0.207033 0.059*
C8 0.6287 (4) 0.2287 (4) 0.10502 (12) 0.0546 (7)
H8A 0.553149 0.128385 0.095886 0.066*
H8B 0.535474 0.334375 0.091454 0.066*
C9 0.9774 (4) 0.0810 (3) 0.08466 (12) 0.0525 (7)
H9A 1.113597 0.087916 0.057129 0.063*
H9B 0.902753 −0.020822 0.076595 0.063*
C10 1.0256 (4) 0.0595 (3) 0.15971 (12) 0.0499 (6)
H10A 1.110342 −0.050791 0.173238 0.06*
H10B 1.11409 0.155146 0.166426 0.06*
O3 0.2656 (3) 0.7140 (3) 0.07107 (9) 0.0598 (5)
O4 0.0053 (3) 0.5296 (3) 0.11199 (9) 0.0620 (5)
C11 0.2728 (4) 0.5764 (3) 0.18855 (12) 0.0399 (6)
C12 0.4646 (4) 0.6537 (3) 0.19936 (13) 0.0484 (6)
H12 0.533917 0.726876 0.162881 0.058*
C13 0.5535 (4) 0.6230 (3) 0.26365 (14) 0.0575 (7)
H13 0.68258 0.675862 0.269499 0.069*
C14 0.4567 (5) 0.5162 (3) 0.31955 (14) 0.0562 (7)
C15 0.2645 (4) 0.4395 (4) 0.30874 (14) 0.0584 (7)
H15 0.195058 0.366932 0.345395 0.07*
C16 0.1748 (4) 0.4689 (3) 0.24468 (13) 0.0496 (6)
H16 0.045866 0.41565 0.238897 0.06*
C17 0.1749 (4) 0.6080 (3) 0.11893 (13) 0.0437 (6)
C18 0.5550 (6) 0.4855 (4) 0.38973 (16) 0.0863 (10)
H18A 0.442848 0.502929 0.424033 0.129*
H18B 0.667715 0.567332 0.389742 0.129*
H18C 0.617002 0.366684 0.400046 0.129*
O5 0.7006 (3) 0.7136 (5) 0.02422 (13) 0.1211 (12)
H21 0.903 (6) 0.338 (4) 0.073 (2) 0.145*
H22 0.807 (6) 0.256 (5) 0.0183 (11) 0.145*
H1W 0.792 (5) 0.667 (5) 0.0534 (17) 0.145*
H2W 0.576 (4) 0.720 (6) 0.045 (2) 0.145*

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.145 (2) 0.132 (2) 0.0477 (14) 0.0055 (18) 0.0100 (15) −0.0001 (14)
O2 0.153 (2) 0.155 (3) 0.0702 (17) 0.044 (2) −0.0390 (17) 0.0148 (17)
N1 0.0427 (11) 0.0478 (12) 0.0358 (11) 0.0059 (9) −0.0018 (9) −0.0064 (9)
N2 0.0540 (13) 0.0562 (14) 0.0357 (11) 0.0002 (11) −0.0042 (10) −0.0041 (10)
N3 0.111 (2) 0.078 (2) 0.0469 (17) −0.0053 (17) −0.0113 (16) −0.0005 (14)
C1 0.0489 (14) 0.0408 (14) 0.0377 (14) 0.0000 (11) −0.0047 (11) −0.0100 (11)
C2 0.0675 (17) 0.0685 (19) 0.0442 (16) 0.0202 (15) 0.0004 (13) −0.0028 (14)
C3 0.083 (2) 0.072 (2) 0.0394 (16) 0.0130 (17) 0.0050 (14) −0.0057 (14)
C4 0.085 (2) 0.0556 (17) 0.0352 (15) 0.0002 (16) −0.0113 (14) −0.0044 (13)
C5 0.0719 (19) 0.083 (2) 0.0515 (19) 0.0176 (17) −0.0203 (15) −0.0060 (16)
C6 0.0564 (16) 0.078 (2) 0.0448 (16) 0.0167 (15) −0.0066 (13) −0.0092 (14)
C7 0.0428 (14) 0.0616 (17) 0.0401 (14) 0.0080 (12) −0.0034 (11) −0.0050 (12)
C8 0.0441 (14) 0.0706 (18) 0.0468 (16) 0.0043 (13) −0.0071 (12) −0.0052 (13)
C9 0.0597 (16) 0.0579 (17) 0.0385 (15) 0.0061 (13) 0.0028 (12) −0.0086 (12)
C10 0.0499 (15) 0.0558 (16) 0.0417 (15) 0.0138 (12) −0.0008 (12) −0.0080 (12)
O3 0.0574 (11) 0.0779 (13) 0.0404 (10) −0.0028 (10) −0.0074 (8) 0.0006 (9)
O4 0.0577 (11) 0.0758 (13) 0.0557 (12) −0.0102 (10) −0.0167 (9) −0.0143 (10)
C11 0.0404 (13) 0.0387 (13) 0.0413 (14) 0.0068 (11) −0.0074 (11) −0.0103 (11)
C12 0.0513 (15) 0.0449 (15) 0.0490 (16) −0.0006 (12) −0.0065 (12) −0.0072 (12)
C13 0.0547 (16) 0.0533 (17) 0.0679 (19) 0.0004 (13) −0.0224 (14) −0.0158 (15)
C14 0.0707 (18) 0.0497 (16) 0.0498 (17) 0.0066 (14) −0.0233 (14) −0.0103 (13)
C15 0.0706 (18) 0.0570 (17) 0.0453 (16) −0.0042 (14) −0.0099 (13) −0.0007 (13)
C16 0.0488 (15) 0.0518 (16) 0.0485 (16) −0.0039 (13) −0.0089 (12) −0.0074 (13)
C17 0.0427 (14) 0.0473 (15) 0.0420 (15) 0.0071 (12) −0.0042 (12) −0.0121 (12)
C18 0.114 (3) 0.079 (2) 0.068 (2) −0.003 (2) −0.0467 (19) −0.0066 (17)
O5 0.0602 (14) 0.210 (3) 0.0697 (16) −0.0101 (18) −0.0093 (12) 0.0407 (18)

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Geometric parameters (Å, º)

O1—N3 1.216 (3) C9—C10 1.500 (3)
O2—N3 1.204 (3) C9—H9A 0.97
N1—C1 1.399 (3) C9—H9B 0.97
N1—C10 1.460 (3) C10—H10A 0.97
N1—C7 1.463 (3) C10—H10B 0.97
N2—C8 1.480 (3) O3—O3 0.000 (5)
N2—C9 1.483 (3) O3—C17 1.259 (3)
N2—H21 0.892 (19) O4—C17 1.254 (3)
N2—H22 0.908 (19) C11—C12 1.387 (3)
N3—C4 1.468 (3) C11—C16 1.389 (3)
C1—C2 1.390 (3) C11—C17 1.498 (3)
C1—C6 1.391 (3) C12—C13 1.379 (3)
C2—C3 1.378 (4) C12—H12 0.93
C2—H2 0.93 C13—C14 1.380 (4)
C3—C4 1.360 (4) C13—H13 0.93
C3—H3 0.93 C14—C15 1.387 (4)
C4—C5 1.356 (4) C14—C18 1.509 (4)
C5—C6 1.377 (4) C15—C16 1.377 (3)
C5—H5 0.93 C15—H15 0.93
C6—H6 0.93 C16—H16 0.93
C7—C8 1.509 (3) C18—H18A 0.96
C7—H7A 0.97 C18—H18B 0.96
C7—H7B 0.97 C18—H18C 0.96
C8—H8A 0.97 O5—H1W 0.843 (19)
C8—H8B 0.97 O5—H2W 0.854 (19)
C1—N1—C10 117.39 (18) N2—C9—H9A 109.6
C1—N1—C7 117.37 (18) C10—C9—H9A 109.6
C10—N1—C7 113.94 (18) N2—C9—H9B 109.6
C8—N2—C9 108.7 (2) C10—C9—H9B 109.6
C8—N2—H21 107 (3) H9A—C9—H9B 108.2
C9—N2—H21 110 (3) N1—C10—C9 112.7 (2)
C8—N2—H22 109 (3) N1—C10—H10A 109.1
C9—N2—H22 110 (3) C9—C10—H10A 109.1
H21—N2—H22 112 (4) N1—C10—H10B 109.1
O2—N3—O1 123.5 (3) C9—C10—H10B 109.1
O2—N3—C4 118.5 (3) H10A—C10—H10B 107.8
O1—N3—C4 117.9 (3) O3—O3—C17 0 (10)
C2—C1—C6 116.8 (2) C12—C11—C16 117.5 (2)
C2—C1—N1 121.7 (2) C12—C11—C17 121.2 (2)
C6—C1—N1 121.4 (2) C16—C11—C17 121.2 (2)
C3—C2—C1 121.6 (3) C13—C12—C11 120.7 (2)
C3—C2—H2 119.2 C13—C12—H12 119.7
C1—C2—H2 119.2 C11—C12—H12 119.7
C4—C3—C2 119.6 (3) C12—C13—C14 122.0 (2)
C4—C3—H3 120.2 C12—C13—H13 119
C2—C3—H3 120.2 C14—C13—H13 119
C5—C4—C3 120.7 (2) C13—C14—C15 117.3 (2)
C5—C4—N3 119.3 (3) C13—C14—C18 121.3 (3)
C3—C4—N3 120.0 (3) C15—C14—C18 121.4 (3)
C4—C5—C6 120.1 (3) C16—C15—C14 121.2 (3)
C4—C5—H5 119.9 C16—C15—H15 119.4
C6—C5—H5 119.9 C14—C15—H15 119.4
C5—C6—C1 121.2 (2) C15—C16—C11 121.3 (2)
C5—C6—H6 119.4 C15—C16—H16 119.3
C1—C6—H6 119.4 C11—C16—H16 119.3
N1—C7—C8 112.6 (2) O4—C17—O3 123.8 (2)
N1—C7—H7A 109.1 O4—C17—O3 123.8 (2)
C8—C7—H7A 109.1 O3—C17—O3 0.0 (2)
N1—C7—H7B 109.1 O4—C17—C11 118.1 (2)
C8—C7—H7B 109.1 O3—C17—C11 118.0 (2)
H7A—C7—H7B 107.8 O3—C17—C11 118.0 (2)
N2—C8—C7 111.1 (2) C14—C18—H18A 109.5
N2—C8—H8A 109.4 C14—C18—H18B 109.5
C7—C8—H8A 109.4 H18A—C18—H18B 109.5
N2—C8—H8B 109.4 C14—C18—H18C 109.5
C7—C8—H8B 109.4 H18A—C18—H18C 109.5
H8A—C8—H8B 108 H18B—C18—H18C 109.5
N2—C9—C10 110.1 (2) H1W—O5—H2W 108 (4)
C10—N1—C1—C2 164.4 (2) C8—N2—C9—C10 −60.7 (3)
C7—N1—C1—C2 22.9 (3) C1—N1—C10—C9 168.3 (2)
C10—N1—C1—C6 −18.9 (3) C7—N1—C10—C9 −48.9 (3)
C7—N1—C1—C6 −160.4 (2) N2—C9—C10—N1 55.7 (3)
C6—C1—C2—C3 −1.2 (4) C16—C11—C12—C13 0.3 (3)
N1—C1—C2—C3 175.6 (3) C17—C11—C12—C13 −179.7 (2)
C1—C2—C3—C4 −0.3 (5) C11—C12—C13—C14 −0.3 (4)
C2—C3—C4—C5 1.3 (5) C12—C13—C14—C15 0.1 (4)
C2—C3—C4—N3 −179.1 (3) C12—C13—C14—C18 −179.4 (3)
O2—N3—C4—C5 −5.0 (4) C13—C14—C15—C16 0.1 (4)
O1—N3—C4—C5 173.8 (3) C18—C14—C15—C16 179.6 (3)
O2—N3—C4—C3 175.5 (3) C14—C15—C16—C11 −0.1 (4)
O1—N3—C4—C3 −5.7 (4) C12—C11—C16—C15 −0.1 (4)
C3—C4—C5—C6 −0.8 (5) C17—C11—C16—C15 179.9 (2)
N3—C4—C5—C6 179.6 (3) O3—O3—C17—O4 0.00 (14)
C4—C5—C6—C1 −0.8 (5) O3—O3—C17—C11 0.0 (2)
C2—C1—C6—C5 1.8 (4) C12—C11—C17—O4 177.7 (2)
N1—C1—C6—C5 −175.0 (3) C16—C11—C17—O4 −2.4 (3)
C1—N1—C7—C8 −170.1 (2) C12—C11—C17—O3 −3.5 (3)
C10—N1—C7—C8 47.0 (3) C16—C11—C17—O3 176.4 (2)
C9—N2—C8—C7 59.5 (3) C12—C11—C17—O3 −3.5 (3)
N1—C7—C8—N2 −52.7 (3) C16—C11—C17—O3 176.4 (2)

4-(4-Nitrophenyl)piperazin-1-ium 4-methylbenzoate monohydrate (IV). Hydrogen-bond geometry (Å, º)

Cg3 is the centroids of the C11–C16 ring.

D—H···A D—H H···A D···A D—H···A
N2—H21···O4i 0.89 (2) 1.93 (2) 2.811 (3) 167 (4)
N2—H22···O3ii 0.91 (2) 1.81 (2) 2.717 (3) 177 (4)
C3—H3···O1iii 0.93 2.54 3.427 (4) 161
C9—H9A···O5iv 0.97 2.31 3.113 (3) 140
O5—H1W···O4i 0.84 (2) 1.92 (2) 2.756 (3) 171 (4)
O5—H2W···O3 0.85 (2) 1.94 (2) 2.772 (3) 164 (4)
C6—H6···Cg3v 0.93 2.93 3.590 (3) 129

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

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Crystal data

2C10H14N3O2+·2C8H7O3·H2O F(000) = 1560
Mr = 736.77 Dx = 1.328 Mg m3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 2899 reflections
a = 15.808 (1) Å θ = 2.6–25.3°
b = 7.5198 (7) Å µ = 0.1 mm1
c = 31.020 (2) Å T = 293 K
β = 92.561 (7)° Prism, orange
V = 3683.8 (5) Å3 0.5 × 0.36 × 0.36 mm
Z = 4

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Data collection

Oxford Diffraction Xcalibur diffractometer 2602 reflections with I > 2σ(I)
ω scans Rint = 0.066
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.3°, θmin = 2.6°
Tmin = 0.958, Tmax = 0.965 h = −19→18
15326 measured reflections k = −9→8
6718 independent reflections l = −37→33

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Refinement

Refinement on F2 Hydrogen site location: mixed
Least-squares matrix: full H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.074 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.9198P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.169 (Δ/σ)max < 0.001
S = 1.00 Δρmax = 0.27 e Å3
6715 reflections Δρmin = −0.18 e Å3
507 parameters Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
45 restraints Extinction coefficient: 0.0029 (4)
0 constraints

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
C1 0.2115 (2) 0.2769 (5) 0.15386 (13) 0.0456 (11)
C2 0.2042 (3) 0.2439 (6) 0.19789 (14) 0.0687 (14)
H2 0.151236 0.21805 0.208209 0.082*
C3 0.2734 (3) 0.2487 (7) 0.22634 (14) 0.0860 (16)
H3 0.26712 0.22698 0.255532 0.103*
C4 0.3512 (3) 0.2855 (7) 0.21153 (15) 0.0702 (14)
C5 0.3613 (3) 0.3157 (6) 0.16906 (15) 0.0722 (14)
H5 0.414916 0.339042 0.159279 0.087*
C6 0.2925 (3) 0.3119 (6) 0.14031 (13) 0.0598 (12)
H6 0.300335 0.333225 0.111231 0.072*
C7 0.1555 (2) 0.2450 (6) 0.07998 (12) 0.0599 (12)
H7A 0.166523 0.119002 0.076636 0.072*
H7B 0.205192 0.309359 0.07138 0.072*
C8 0.0813 (3) 0.2965 (6) 0.05086 (13) 0.0690 (13)
H8A 0.075136 0.42483 0.050937 0.083*
H8B 0.09152 0.259489 0.021595 0.083*
C9 −0.0117 (3) 0.2610 (6) 0.10976 (14) 0.0669 (13)
H9A −0.062504 0.202151 0.118906 0.08*
H9B −0.020149 0.38837 0.112112 0.08*
C10 0.0624 (2) 0.2059 (6) 0.13852 (12) 0.0631 (13)
H10A 0.052793 0.242915 0.16785 0.076*
H10B 0.066876 0.077208 0.138331 0.076*
C11 0.9721 (3) 0.2971 (6) 0.30361 (13) 0.0510 (11)
C12 0.8980 (3) 0.2023 (6) 0.30443 (12) 0.0563 (12)
H12 0.888658 0.13067 0.328178 0.068*
C13 0.8365 (3) 0.2095 (6) 0.27110 (14) 0.0632 (13)
H13 0.78756 0.14142 0.272281 0.076*
C14 0.8487 (3) 0.3182 (6) 0.23643 (14) 0.0628 (12)
C15 0.9229 (3) 0.4129 (6) 0.23467 (13) 0.0649 (13)
H15 0.93208 0.484494 0.210883 0.078*
C16 0.9839 (3) 0.4028 (6) 0.26775 (14) 0.0626 (13)
H16 1.033592 0.46798 0.26601 0.075*
C17 1.0355 (3) 0.2887 (7) 0.34129 (16) 0.0608 (13)
C18 0.7146 (3) 0.2457 (8) 0.20218 (17) 0.118 (2)
H18C 0.681472 0.273815 0.176387 0.178*
H18B 0.725759 0.120242 0.20308 0.178*
H18A 0.684002 0.279268 0.226948 0.178*
C19 0.3816 (3) 0.5044 (6) −0.09170 (13) 0.0503 (11)
C20 0.3778 (3) 0.6432 (6) −0.06180 (13) 0.0582 (12)
H20 0.326082 0.697741 −0.057457 0.07*
C21 0.4478 (3) 0.6998 (6) −0.03904 (13) 0.0603 (12)
H21 0.443054 0.790435 −0.018877 0.072*
C22 0.5251 (2) 0.6260 (6) −0.04523 (13) 0.0499 (11)
C23 0.5330 (3) 0.4942 (6) −0.07542 (14) 0.0610 (12)
H23 0.58581 0.445412 −0.080183 0.073*
C24 0.4629 (3) 0.4354 (6) −0.09836 (13) 0.0623 (13)
H24 0.468943 0.347143 −0.119 0.075*
C25 0.3099 (3) 0.2720 (7) −0.13618 (14) 0.0722 (14)
H25A 0.36547 0.248859 −0.147048 0.087*
H25B 0.269401 0.27516 −0.160582 0.087*
C26 0.2867 (3) 0.1245 (6) −0.10589 (14) 0.0694 (13)
H26A 0.284623 0.011999 −0.121195 0.083*
H26B 0.329107 0.115475 −0.082393 0.083*
C27 0.1998 (2) 0.3414 (6) −0.06853 (12) 0.0579 (12)
H27A 0.237409 0.345068 −0.042968 0.07*
H27B 0.142682 0.365292 −0.059877 0.07*
C28 0.2258 (2) 0.4799 (6) −0.10009 (13) 0.0583 (12)
H28A 0.186099 0.480675 −0.124849 0.07*
H28B 0.224623 0.596261 −0.086644 0.07*
C29 0.2315 (2) 0.8165 (5) 0.03520 (12) 0.0442 (10)
C30 0.3063 (2) 0.9094 (5) 0.03221 (13) 0.0517 (11)
H30 0.319956 0.957242 0.005761 0.062*
C31 0.3609 (2) 0.9330 (6) 0.06743 (15) 0.0597 (12)
H31 0.411473 0.994162 0.064463 0.072*
C32 0.3412 (3) 0.8662 (6) 0.10717 (15) 0.0570 (12)
C33 0.2661 (3) 0.7752 (6) 0.11108 (13) 0.0590 (12)
H33 0.251489 0.731519 0.137782 0.071*
C34 0.2130 (2) 0.7495 (5) 0.07521 (13) 0.0524 (11)
H34 0.163238 0.685277 0.077981 0.063*
C35 0.1734 (3) 0.7879 (6) −0.00372 (14) 0.0459 (11)
C36 0.3801 (3) 0.8360 (7) 0.18157 (17) 0.1098 (19)
H36C 0.42611 0.863024 0.201777 0.165*
H36B 0.329805 0.895356 0.190161 0.165*
H36A 0.370656 0.709953 0.181018 0.165*
N1 0.14171 (19) 0.2823 (4) 0.12508 (10) 0.0475 (9)
N2 0.0026 (2) 0.2144 (5) 0.06465 (13) 0.0581 (10)
N3 0.4265 (6) 0.2464 (13) 0.2410 (3) 0.075 (2) 0.519 (6)
N3' 0.4213 (6) 0.3345 (15) 0.2420 (3) 0.075 (2) 0.481 (6)
N4 0.3106 (2) 0.4437 (5) −0.11425 (10) 0.0583 (10)
N5 0.2034 (2) 0.1639 (5) −0.08869 (12) 0.0612 (10)
N6 0.5983 (2) 0.6796 (6) −0.01867 (13) 0.0650 (11)
O1 0.4960 (7) 0.2571 (14) 0.2266 (4) 0.099 (2) 0.519 (6)
O1' 0.4904 (8) 0.3633 (14) 0.2283 (4) 0.099 (2) 0.481 (6)
O2 0.4177 (6) 0.2116 (13) 0.2788 (3) 0.097 (2) 0.519 (6)
O2' 0.4086 (6) 0.3408 (15) 0.2797 (3) 0.097 (2) 0.481 (6)
O3 1.1003 (2) 0.3818 (4) 0.33942 (9) 0.0826 (10)
O4 1.0196 (2) 0.1889 (4) 0.37194 (10) 0.0789 (10)
O5 0.7922 (2) 0.3398 (5) 0.20234 (9) 0.0895 (11)
O6 0.58811 (19) 0.7838 (5) 0.01114 (11) 0.0827 (11)
O7 0.66853 (19) 0.6203 (5) −0.02668 (10) 0.0881 (11)
O8 0.10807 (17) 0.6951 (4) 0.00037 (8) 0.0590 (8)
O9 0.19207 (16) 0.8596 (4) −0.03853 (9) 0.0593 (8)
O10 0.40056 (18) 0.8950 (4) 0.13979 (10) 0.0790 (10)
O11 1.00751 (19) 0.3517 (4) 0.44766 (10) 0.0649 (9)
H21N −0.0388 (19) 0.252 (5) 0.0468 (11) 0.078*
H22N 0.007 (3) 0.099 (3) 0.0609 (12) 0.078*
H51N 0.190 (2) 0.077 (4) −0.0717 (11) 0.078*
H52N 0.164 (2) 0.153 (6) −0.1110 (9) 0.078*
H11O 1.010 (3) 0.296 (5) 0.4244 (9) 0.078*
H12O 0.969 (2) 0.305 (5) 0.4618 (12) 0.078*

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.043 (3) 0.040 (3) 0.054 (3) 0.002 (2) 0.000 (2) −0.002 (2)
C2 0.056 (3) 0.100 (4) 0.051 (3) −0.008 (3) 0.007 (3) 0.001 (3)
C3 0.073 (3) 0.145 (5) 0.039 (3) −0.011 (4) −0.005 (3) 0.004 (3)
C4 0.052 (3) 0.108 (4) 0.050 (3) −0.009 (3) −0.013 (2) 0.001 (3)
C5 0.052 (3) 0.107 (4) 0.057 (3) −0.017 (3) −0.001 (3) 0.005 (3)
C6 0.049 (3) 0.082 (4) 0.048 (3) −0.005 (3) −0.006 (2) 0.009 (2)
C7 0.050 (3) 0.082 (3) 0.047 (3) −0.009 (3) −0.002 (2) 0.002 (2)
C8 0.064 (3) 0.077 (3) 0.064 (3) −0.023 (3) −0.018 (2) 0.017 (3)
C9 0.052 (3) 0.076 (4) 0.073 (4) −0.003 (3) −0.003 (2) −0.015 (3)
C10 0.052 (3) 0.089 (4) 0.048 (3) −0.013 (3) 0.000 (2) −0.003 (2)
C11 0.055 (3) 0.049 (3) 0.049 (3) 0.004 (3) 0.004 (2) 0.002 (2)
C12 0.071 (3) 0.059 (3) 0.039 (3) 0.007 (3) 0.006 (2) 0.008 (2)
C13 0.058 (3) 0.074 (4) 0.058 (3) −0.010 (3) 0.000 (2) 0.010 (3)
C14 0.064 (3) 0.071 (4) 0.051 (3) 0.007 (3) −0.012 (3) 0.004 (3)
C15 0.068 (3) 0.070 (4) 0.056 (3) −0.009 (3) −0.004 (3) 0.018 (2)
C16 0.058 (3) 0.064 (3) 0.065 (3) −0.009 (3) 0.000 (3) 0.009 (3)
C17 0.063 (3) 0.057 (4) 0.062 (3) 0.014 (3) −0.010 (3) −0.011 (3)
C18 0.103 (5) 0.148 (6) 0.100 (4) −0.040 (4) −0.047 (3) 0.023 (4)
C19 0.044 (3) 0.065 (3) 0.042 (3) −0.002 (3) 0.007 (2) 0.009 (2)
C20 0.038 (3) 0.071 (3) 0.066 (3) 0.003 (3) 0.002 (2) −0.004 (3)
C21 0.046 (3) 0.071 (3) 0.064 (3) −0.002 (3) 0.008 (2) −0.009 (2)
C22 0.035 (3) 0.064 (3) 0.051 (3) −0.007 (2) 0.002 (2) 0.009 (2)
C23 0.038 (3) 0.068 (3) 0.077 (3) 0.004 (3) 0.012 (2) 0.005 (3)
C24 0.050 (3) 0.067 (3) 0.071 (3) −0.003 (3) 0.015 (3) −0.011 (2)
C25 0.063 (3) 0.100 (4) 0.054 (3) −0.009 (3) 0.006 (2) −0.023 (3)
C26 0.069 (3) 0.068 (4) 0.070 (3) 0.003 (3) −0.008 (3) −0.015 (3)
C27 0.049 (3) 0.070 (3) 0.054 (3) −0.004 (3) −0.003 (2) −0.012 (3)
C28 0.042 (3) 0.063 (3) 0.069 (3) −0.006 (2) −0.008 (2) 0.001 (3)
C29 0.043 (2) 0.045 (3) 0.045 (3) 0.005 (2) 0.004 (2) −0.003 (2)
C30 0.044 (3) 0.063 (3) 0.049 (3) 0.006 (2) 0.004 (2) 0.007 (2)
C31 0.044 (3) 0.071 (3) 0.064 (3) −0.005 (2) −0.005 (2) −0.001 (3)
C32 0.053 (3) 0.064 (3) 0.053 (3) 0.012 (3) −0.013 (3) −0.008 (3)
C33 0.062 (3) 0.067 (3) 0.048 (3) −0.001 (3) −0.005 (2) 0.005 (2)
C34 0.052 (3) 0.055 (3) 0.050 (3) −0.004 (2) −0.002 (2) 0.006 (2)
C35 0.048 (3) 0.040 (3) 0.050 (3) 0.009 (2) −0.005 (2) −0.002 (2)
C36 0.117 (5) 0.125 (5) 0.083 (4) 0.008 (4) −0.035 (3) −0.004 (4)
N1 0.041 (2) 0.055 (2) 0.046 (2) −0.0042 (18) −0.0010 (17) −0.0018 (17)
N2 0.055 (3) 0.047 (2) 0.070 (3) −0.005 (2) −0.0165 (19) 0.004 (2)
N3 0.072 (3) 0.081 (4) 0.070 (3) −0.002 (3) −0.004 (2) −0.001 (3)
N3' 0.072 (3) 0.081 (4) 0.070 (3) −0.002 (3) −0.004 (2) −0.001 (3)
N4 0.051 (2) 0.072 (3) 0.052 (2) −0.005 (2) 0.0048 (19) −0.002 (2)
N5 0.059 (3) 0.063 (3) 0.061 (3) −0.012 (2) −0.009 (2) 0.010 (2)
N6 0.048 (3) 0.084 (3) 0.064 (3) −0.012 (3) 0.003 (2) 0.021 (2)
O1 0.075 (3) 0.127 (7) 0.092 (3) −0.011 (5) −0.020 (2) −0.001 (6)
O1' 0.075 (3) 0.127 (7) 0.092 (3) −0.011 (5) −0.020 (2) −0.001 (6)
O2 0.097 (3) 0.131 (6) 0.062 (3) −0.003 (5) −0.015 (2) 0.001 (5)
O2' 0.097 (3) 0.131 (6) 0.062 (3) −0.003 (5) −0.015 (2) 0.001 (5)
O3 0.073 (2) 0.088 (3) 0.084 (2) −0.010 (2) −0.0291 (18) 0.0096 (18)
O4 0.106 (3) 0.069 (2) 0.060 (2) 0.003 (2) −0.0170 (18) 0.0134 (18)
O5 0.082 (2) 0.115 (3) 0.070 (2) −0.013 (2) −0.0256 (19) 0.0253 (19)
O6 0.072 (2) 0.110 (3) 0.066 (2) −0.023 (2) 0.0016 (18) −0.002 (2)
O7 0.046 (2) 0.128 (3) 0.090 (2) −0.001 (2) 0.0000 (18) 0.023 (2)
O8 0.0548 (18) 0.061 (2) 0.060 (2) −0.0126 (17) −0.0085 (14) 0.0027 (15)
O9 0.0639 (19) 0.066 (2) 0.0473 (19) 0.0027 (16) −0.0024 (15) 0.0080 (15)
O10 0.072 (2) 0.102 (3) 0.061 (2) 0.0032 (19) −0.0220 (18) −0.0004 (19)
O11 0.063 (2) 0.064 (2) 0.069 (2) 0.0012 (18) 0.0089 (17) −0.0012 (17)

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Geometric parameters (Å, º)

C1—N1 1.388 (4) C21—H21 0.93
C1—C6 1.391 (5) C22—C23 1.373 (5)
C1—C2 1.398 (5) C22—N6 1.448 (5)
C2—C3 1.375 (6) C23—C24 1.363 (5)
C2—H2 0.93 C23—H23 0.93
C3—C4 1.359 (6) C24—H24 0.93
C3—H3 0.93 C25—N4 1.459 (5)
C4—C5 1.354 (5) C25—C26 1.509 (6)
C4—N3' 1.471 (10) C25—H25A 0.97
C4—N3 1.499 (9) C25—H25B 0.97
C5—C6 1.375 (5) C26—N5 1.474 (5)
C5—H5 0.93 C26—H26A 0.97
C6—H6 0.93 C26—H26B 0.97
C7—N1 1.453 (4) C27—N5 1.476 (5)
C7—C8 1.499 (5) C27—C28 1.499 (5)
C7—H7A 0.97 C27—H27A 0.97
C7—H7B 0.97 C27—H27B 0.97
C8—N2 1.469 (5) C28—N4 1.455 (4)
C8—H8A 0.97 C28—H28A 0.97
C8—H8B 0.97 C28—H28B 0.97
C9—N2 1.470 (5) C29—C30 1.379 (5)
C9—C10 1.499 (5) C29—C34 1.383 (5)
C9—H9A 0.97 C29—C35 1.499 (5)
C9—H9B 0.97 C30—C31 1.374 (5)
C10—N1 1.457 (4) C30—H30 0.93
C10—H10A 0.97 C31—C32 1.379 (5)
C10—H10B 0.97 C31—H31 0.93
C11—C12 1.372 (5) C32—O10 1.366 (4)
C11—C16 1.387 (5) C32—C33 1.380 (5)
C11—C17 1.506 (6) C33—C34 1.377 (5)
C12—C13 1.388 (5) C33—H33 0.93
C12—H12 0.93 C34—H34 0.93
C13—C14 1.371 (5) C35—O9 1.254 (4)
C13—H13 0.93 C35—O8 1.258 (4)
C14—O5 1.363 (5) C36—O10 1.421 (5)
C14—C15 1.375 (5) C36—H36C 0.96
C15—C16 1.378 (5) C36—H36B 0.96
C15—H15 0.93 C36—H36A 0.96
C16—H16 0.93 N2—H21N 0.884 (18)
C17—O3 1.245 (5) N2—H22N 0.882 (18)
C17—O4 1.246 (5) N3—O1 1.208 (9)
C18—O5 1.416 (5) N3—O2 1.213 (9)
C18—H18C 0.96 N3'—O2' 1.196 (9)
C18—H18B 0.96 N3'—O1' 1.210 (10)
C18—H18A 0.96 N5—H51N 0.872 (18)
C19—N4 1.374 (4) N5—H52N 0.910 (18)
C19—C20 1.399 (5) N6—O6 1.228 (4)
C19—C24 1.410 (5) N6—O7 1.232 (4)
C20—C21 1.354 (5) O11—H11O 0.836 (18)
C20—H20 0.93 O11—H12O 0.838 (18)
C21—C22 1.363 (5)
N1—C1—C6 121.1 (4) C22—C23—H23 120.2
N1—C1—C2 122.4 (4) C23—C24—C19 121.9 (4)
C6—C1—C2 116.5 (4) C23—C24—H24 119
C3—C2—C1 121.6 (4) C19—C24—H24 119
C3—C2—H2 119.2 N4—C25—C26 110.9 (3)
C1—C2—H2 119.2 N4—C25—H25A 109.5
C4—C3—C2 119.6 (4) C26—C25—H25A 109.5
C4—C3—H3 120.2 N4—C25—H25B 109.5
C2—C3—H3 120.2 C26—C25—H25B 109.5
C5—C4—C3 120.7 (4) H25A—C25—H25B 108
C5—C4—N3' 117.8 (6) N5—C26—C25 108.9 (4)
C3—C4—N3' 120.0 (6) N5—C26—H26A 109.9
C5—C4—N3 120.2 (6) C25—C26—H26A 109.9
C3—C4—N3 117.3 (6) N5—C26—H26B 109.9
C4—C5—C6 120.2 (4) C25—C26—H26B 109.9
C4—C5—H5 119.9 H26A—C26—H26B 108.3
C6—C5—H5 119.9 N5—C27—C28 109.5 (3)
C5—C6—C1 121.3 (4) N5—C27—H27A 109.8
C5—C6—H6 119.3 C28—C27—H27A 109.8
C1—C6—H6 119.3 N5—C27—H27B 109.8
N1—C7—C8 112.5 (3) C28—C27—H27B 109.8
N1—C7—H7A 109.1 H27A—C27—H27B 108.2
C8—C7—H7A 109.1 N4—C28—C27 110.5 (3)
N1—C7—H7B 109.1 N4—C28—H28A 109.5
C8—C7—H7B 109.1 C27—C28—H28A 109.5
H7A—C7—H7B 107.8 N4—C28—H28B 109.5
N2—C8—C7 111.5 (3) C27—C28—H28B 109.5
N2—C8—H8A 109.3 H28A—C28—H28B 108.1
C7—C8—H8A 109.3 C30—C29—C34 117.5 (4)
N2—C8—H8B 109.3 C30—C29—C35 120.9 (4)
C7—C8—H8B 109.3 C34—C29—C35 121.6 (4)
H8A—C8—H8B 108 C31—C30—C29 121.5 (4)
N2—C9—C10 110.5 (3) C31—C30—H30 119.3
N2—C9—H9A 109.5 C29—C30—H30 119.3
C10—C9—H9A 109.5 C30—C31—C32 120.3 (4)
N2—C9—H9B 109.5 C30—C31—H31 119.8
C10—C9—H9B 109.5 C32—C31—H31 119.8
H9A—C9—H9B 108.1 O10—C32—C31 115.4 (4)
N1—C10—C9 112.3 (3) O10—C32—C33 125.3 (4)
N1—C10—H10A 109.1 C31—C32—C33 119.2 (4)
C9—C10—H10A 109.1 C34—C33—C32 119.6 (4)
N1—C10—H10B 109.1 C34—C33—H33 120.2
C9—C10—H10B 109.1 C32—C33—H33 120.2
H10A—C10—H10B 107.9 C33—C34—C29 121.8 (4)
C12—C11—C16 117.2 (4) C33—C34—H34 119.1
C12—C11—C17 120.2 (4) C29—C34—H34 119.1
C16—C11—C17 122.5 (4) O9—C35—O8 123.4 (4)
C11—C12—C13 122.4 (4) O9—C35—C29 118.2 (4)
C11—C12—H12 118.8 O8—C35—C29 118.3 (4)
C13—C12—H12 118.8 O10—C36—H36C 109.5
C14—C13—C12 119.3 (4) O10—C36—H36B 109.5
C14—C13—H13 120.4 H36C—C36—H36B 109.5
C12—C13—H13 120.4 O10—C36—H36A 109.5
O5—C14—C13 124.7 (4) H36C—C36—H36A 109.5
O5—C14—C15 116.0 (4) H36B—C36—H36A 109.5
C13—C14—C15 119.3 (4) C1—N1—C7 117.7 (3)
C14—C15—C16 120.7 (4) C1—N1—C10 118.2 (3)
C14—C15—H15 119.6 C7—N1—C10 111.6 (3)
C16—C15—H15 119.6 C8—N2—C9 110.2 (3)
C15—C16—C11 121.0 (4) C8—N2—H21N 107 (3)
C15—C16—H16 119.5 C9—N2—H21N 112 (3)
C11—C16—H16 119.5 C8—N2—H22N 108 (3)
O3—C17—O4 124.6 (4) C9—N2—H22N 112 (3)
O3—C17—C11 117.5 (5) H21N—N2—H22N 107 (4)
O4—C17—C11 117.9 (5) O1—N3—O2 121.2 (11)
O5—C18—H18C 109.5 O1—N3—C4 118.2 (10)
O5—C18—H18B 109.5 O2—N3—C4 120.6 (9)
H18C—C18—H18B 109.5 O2'—N3'—O1' 122.0 (11)
O5—C18—H18A 109.5 O2'—N3'—C4 119.0 (9)
H18C—C18—H18A 109.5 O1'—N3'—C4 119.0 (10)
H18B—C18—H18A 109.5 C19—N4—C28 121.8 (3)
N4—C19—C20 121.8 (4) C19—N4—C25 121.4 (4)
N4—C19—C24 122.2 (4) C28—N4—C25 108.6 (3)
C20—C19—C24 116.0 (4) C26—N5—C27 112.8 (3)
C21—C20—C19 121.5 (4) C26—N5—H51N 108 (3)
C21—C20—H20 119.3 C27—N5—H51N 114 (3)
C19—C20—H20 119.3 C26—N5—H52N 107 (3)
C20—C21—C22 121.0 (4) C27—N5—H52N 112 (3)
C20—C21—H21 119.5 H51N—N5—H52N 103 (4)
C22—C21—H21 119.5 O6—N6—O7 122.1 (4)
C21—C22—C23 120.0 (4) O6—N6—C22 118.5 (4)
C21—C22—N6 120.4 (4) O7—N6—C22 119.3 (4)
C23—C22—N6 119.6 (4) C14—O5—C18 118.7 (4)
C24—C23—C22 119.6 (4) C32—O10—C36 116.7 (4)
C24—C23—H23 120.2 H11O—O11—H12O 108 (5)
N1—C1—C2—C3 −176.3 (4) O10—C32—C33—C34 −177.5 (4)
C6—C1—C2—C3 1.0 (6) C31—C32—C33—C34 1.3 (6)
C1—C2—C3—C4 −0.3 (8) C32—C33—C34—C29 −1.7 (6)
C2—C3—C4—C5 −0.7 (8) C30—C29—C34—C33 0.7 (6)
C2—C3—C4—N3' 164.9 (6) C35—C29—C34—C33 179.9 (4)
C2—C3—C4—N3 −165.5 (6) C30—C29—C35—O9 −4.2 (5)
C3—C4—C5—C6 0.9 (8) C34—C29—C35—O9 176.6 (3)
N3'—C4—C5—C6 −165.0 (6) C30—C29—C35—O8 176.7 (3)
N3—C4—C5—C6 165.4 (6) C34—C29—C35—O8 −2.5 (5)
C4—C5—C6—C1 −0.2 (7) C6—C1—N1—C7 27.3 (5)
N1—C1—C6—C5 176.6 (4) C2—C1—N1—C7 −155.5 (4)
C2—C1—C6—C5 −0.7 (6) C6—C1—N1—C10 166.2 (4)
N1—C7—C8—N2 −54.0 (5) C2—C1—N1—C10 −16.6 (6)
N2—C9—C10—N1 56.1 (5) C8—C7—N1—C1 −166.4 (3)
C16—C11—C12—C13 0.2 (6) C8—C7—N1—C10 52.2 (4)
C17—C11—C12—C13 178.1 (4) C9—C10—N1—C1 165.3 (3)
C11—C12—C13—C14 −1.6 (7) C9—C10—N1—C7 −53.4 (5)
C12—C13—C14—O5 −178.3 (4) C7—C8—N2—C9 55.9 (5)
C12—C13—C14—C15 2.3 (7) C10—C9—N2—C8 −56.8 (4)
O5—C14—C15—C16 179.0 (4) C5—C4—N3—O1 5.9 (11)
C13—C14—C15—C16 −1.6 (7) C3—C4—N3—O1 170.9 (8)
C14—C15—C16—C11 0.1 (7) C5—C4—N3—O2 −176.8 (7)
C12—C11—C16—C15 0.6 (6) C3—C4—N3—O2 −11.8 (11)
C17—C11—C16—C15 −177.3 (4) C5—C4—N3'—O2' 166.2 (8)
C12—C11—C17—O3 −177.7 (4) C3—C4—N3'—O2' 0.2 (12)
C16—C11—C17—O3 0.1 (6) C5—C4—N3'—O1' −15.5 (12)
C12—C11—C17—O4 2.6 (6) C3—C4—N3'—O1' 178.5 (9)
C16—C11—C17—O4 −179.5 (4) C20—C19—N4—C28 −18.5 (6)
N4—C19—C20—C21 178.6 (4) C24—C19—N4—C28 163.8 (4)
C24—C19—C20—C21 −3.6 (6) C20—C19—N4—C25 −163.3 (4)
C19—C20—C21—C22 1.6 (6) C24—C19—N4—C25 19.0 (6)
C20—C21—C22—C23 1.1 (6) C27—C28—N4—C19 −86.8 (5)
C20—C21—C22—N6 −175.8 (4) C27—C28—N4—C25 61.9 (4)
C21—C22—C23—C24 −1.4 (6) C26—C25—N4—C19 86.9 (4)
N6—C22—C23—C24 175.5 (4) C26—C25—N4—C28 −61.9 (4)
C22—C23—C24—C19 −0.8 (6) C25—C26—N5—C27 −54.1 (5)
N4—C19—C24—C23 −179.0 (4) C28—C27—N5—C26 54.7 (4)
C20—C19—C24—C23 3.2 (6) C21—C22—N6—O6 4.5 (6)
N4—C25—C26—N5 57.6 (5) C23—C22—N6—O6 −172.4 (4)
N5—C27—C28—N4 −58.0 (4) C21—C22—N6—O7 −175.1 (4)
C34—C29—C30—C31 0.8 (6) C23—C22—N6—O7 8.0 (6)
C35—C29—C30—C31 −178.5 (4) C13—C14—O5—C18 0.5 (7)
C29—C30—C31—C32 −1.2 (6) C15—C14—O5—C18 179.9 (4)
C30—C31—C32—O10 179.1 (4) C31—C32—O10—C36 176.8 (4)
C30—C31—C32—C33 0.2 (6) C33—C32—O10—C36 −4.4 (6)

4-(4-Nitrophenyl)piperazin-1-ium 4-methoxybenzoate hemihydrate (V). Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
C7—H7B···O7i 0.97 2.54 3.451 (5) 157
C9—H9B···O4ii 0.97 2.31 3.270 (5) 169
C20—H20···O9 0.93 2.53 3.461 (5) 174
C25—H25A···O2aiii 0.97 2.5 3.206 (10) 130
C25—H25A···O2′biii 0.97 2.49 3.212 (11) 131
C27—H27A···O7i 0.97 2.58 3.548 (5) 175
C28—H28B···O9 0.97 2.55 3.489 (5) 164
C36—H36C···O1′bii 0.96 2.49 3.395 (14) 158
N2—H21N···O8iv 0.88 (2) 1.83 (2) 2.697 (4) 166 (4)
N2—H21N···O9iv 0.88 (2) 2.57 (3) 3.196 (4) 129 (3)
N2—H22N···O11v 0.88 (2) 1.89 (2) 2.758 (5) 169 (4)
N5—H51N···O9vi 0.87 (2) 1.93 (2) 2.778 (5) 164 (4)
N5—H52N···O3vii 0.91 (2) 1.82 (2) 2.724 (5) 171 (4)
O11—H11O···O4 0.84 (2) 1.83 (2) 2.663 (4) 176 (4)
O11—H12O···O8v 0.84 (2) 1.92 (2) 2.754 (4) 173 (4)

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

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Crystal data

C10H14N3O2+·C9H9O3 Z = 4
Mr = 373.4 F(000) = 792
Triclinic, P1 Dx = 1.324 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 7.874 (1) Å Cell parameters from 4134 reflections
b = 9.263 (1) Å θ = 2.4–28.0°
c = 27.996 (3) Å µ = 0.10 mm1
α = 81.030 (6)° T = 293 K
β = 85.675 (6)° Plate, yellow
γ = 68.229 (5)° 0.44 × 0.32 × 0.08 mm
V = 1872.8 (4) Å3

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Data collection

Oxford Diffraction Xcalibur diffractometer 3803 reflections with I > 2σ(I)
ω scans Rint = 0.027
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) θmax = 25.4°, θmin = 2.4°
Tmin = 0.963, Tmax = 0.992 h = −9→5
13344 measured reflections k = −11→10
6868 independent reflections l = −33→33

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Refinement

Refinement on F2 0 constraints
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.7484P] where P = (Fo2 + 2Fc2)/3
S = 1.05 (Δ/σ)max < 0.001
6858 reflections Δρmax = 0.23 e Å3
501 parameters Δρmin = −0.22 e Å3
16 restraints

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). 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.

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 −0.3466 (3) 0.6545 (4) 0.40786 (9) 0.1126 (10)
O2 −0.1630 (3) 0.5811 (3) 0.46683 (9) 0.0901 (8)
N3 −0.1931 (4) 0.6107 (3) 0.42384 (10) 0.0667 (7)
N1 0.3914 (3) 0.5404 (2) 0.29014 (7) 0.0412 (5)
N2 0.6838 (3) 0.4199 (3) 0.22275 (9) 0.0486 (6)
C1 0.2485 (3) 0.5547 (3) 0.32330 (9) 0.0364 (6)
C2 0.0659 (4) 0.6276 (3) 0.30870 (10) 0.0452 (7)
H2 0.041054 0.663561 0.276117 0.054*
C3 −0.0759 (4) 0.6467 (3) 0.34138 (10) 0.0487 (7)
H3 −0.195824 0.69631 0.330993 0.058*
C4 −0.0417 (4) 0.5927 (3) 0.38966 (10) 0.0470 (7)
C5 0.1352 (4) 0.5197 (3) 0.40558 (10) 0.0460 (7)
H5 0.157333 0.483265 0.438246 0.055*
C6 0.2787 (4) 0.5009 (3) 0.37309 (10) 0.0430 (7)
H6 0.397837 0.451799 0.384052 0.052*
C7 0.5772 (3) 0.4477 (3) 0.30663 (10) 0.0473 (7)
H7A 0.588757 0.338899 0.315234 0.057*
H7B 0.597413 0.484321 0.33554 0.057*
C8 0.7216 (4) 0.4565 (4) 0.26954 (10) 0.0539 (8)
H8A 0.725864 0.561056 0.265102 0.065*
H8B 0.839991 0.382613 0.280859 0.065*
C9 0.5080 (4) 0.5395 (3) 0.20545 (10) 0.0528 (8)
H9A 0.482935 0.520499 0.174084 0.063*
H9B 0.516375 0.642512 0.201592 0.063*
C10 0.3546 (4) 0.5366 (4) 0.23985 (9) 0.0527 (8)
H10A 0.245506 0.626087 0.229683 0.063*
H10B 0.329888 0.442345 0.238274 0.063*
O3 −0.0728 (3) 0.4331 (2) 0.15512 (7) 0.0578 (5)
O4 0.1149 (2) 0.2978 (2) 0.21489 (7) 0.0532 (5)
O5 0.6778 (3) 0.3001 (3) 0.03965 (7) 0.0734 (7)
C11 0.2434 (4) 0.3357 (3) 0.13647 (9) 0.0400 (6)
C12 0.4193 (4) 0.2483 (3) 0.15096 (10) 0.0518 (8)
H12 0.438717 0.198421 0.182667 0.062*
C13 0.5679 (4) 0.2321 (4) 0.11995 (10) 0.0572 (8)
H13 0.685415 0.171644 0.130663 0.069*
C14 0.5409 (4) 0.3059 (3) 0.07314 (10) 0.0524 (8)
C15 0.3656 (4) 0.3930 (4) 0.05764 (10) 0.0609 (9)
H15 0.346406 0.442258 0.02587 0.073*
C16 0.2192 (4) 0.4072 (3) 0.08898 (10) 0.0520 (8)
H16 0.101521 0.466057 0.078056 0.062*
C17 0.0851 (4) 0.3564 (3) 0.17148 (10) 0.0424 (7)
C18 0.8615 (4) 0.2090 (4) 0.05351 (12) 0.0820 (11)
H18A 0.874909 0.100553 0.064059 0.098*
H18B 0.894362 0.249403 0.079923 0.098*
C19 0.9824 (5) 0.2199 (5) 0.01002 (14) 0.1126 (16)
H19A 1.106148 0.152009 0.017216 0.169*
H19B 0.976652 0.32615 0.001769 0.169*
H19C 0.941525 0.188565 −0.016723 0.169*
O6 0.1516 (4) 0.7336 (4) 0.60499 (10) 0.1157 (11)
O7 0.1799 (4) 0.9508 (4) 0.61439 (10) 0.1162 (11)
N6 0.1845 (4) 0.8525 (5) 0.58929 (11) 0.0830 (10)
N4 0.2839 (3) 0.9838 (3) 0.38867 (8) 0.0490 (6)
N5 0.2937 (3) 1.0699 (3) 0.28629 (8) 0.0462 (6)
C20 0.2721 (4) 0.9472 (3) 0.43812 (10) 0.0459 (7)
C21 0.2534 (4) 0.8084 (4) 0.45928 (11) 0.0653 (9)
H21 0.259467 0.733784 0.439839 0.078*
C22 0.2260 (5) 0.7782 (4) 0.50814 (12) 0.0747 (10)
H22 0.211482 0.684754 0.521174 0.09*
C23 0.2199 (4) 0.8824 (5) 0.53759 (11) 0.0636 (9)
C24 0.2430 (5) 1.0184 (5) 0.51872 (13) 0.0783 (11)
H24 0.240692 1.089852 0.538938 0.094*
C25 0.2700 (5) 1.0504 (4) 0.46951 (12) 0.0711 (10)
H25 0.287119 1.143254 0.457048 0.085*
C26 0.3867 (4) 1.0795 (3) 0.36697 (10) 0.0563 (8)
H26A 0.51213 1.012589 0.360971 0.068*
H26B 0.3881 1.149872 0.389107 0.068*
C27 0.3030 (4) 1.1732 (3) 0.32039 (10) 0.0539 (8)
H27A 0.180752 1.245608 0.326783 0.065*
H27B 0.375328 1.234293 0.305927 0.065*
C28 0.1907 (4) 0.9701 (3) 0.30890 (10) 0.0498 (7)
H28A 0.193308 0.897196 0.28723 0.06*
H28B 0.064102 1.035801 0.314055 0.06*
C29 0.2714 (4) 0.8803 (3) 0.35626 (10) 0.0529 (8)
H29A 0.196135 0.822751 0.371369 0.064*
H29B 0.392544 0.804857 0.35057 0.064*
O8 −0.3777 (3) 0.8954 (2) 0.25237 (8) 0.0629 (6)
O9 −0.3341 (3) 1.1185 (2) 0.25354 (7) 0.0569 (5)
O10 0.2958 (3) 0.8011 (3) 0.10557 (8) 0.0771 (7)
C30 −0.1331 (3) 0.9365 (3) 0.20503 (9) 0.0408 (6)
C31 −0.1058 (4) 0.8152 (3) 0.17834 (10) 0.0508 (7)
H31 −0.185001 0.760423 0.183038 0.061*
C32 0.0357 (4) 0.7741 (3) 0.14506 (11) 0.0555 (8)
H32 0.049421 0.694181 0.127006 0.067*
C33 0.1575 (4) 0.8517 (3) 0.13846 (10) 0.0511 (7)
C34 0.1341 (4) 0.9716 (3) 0.16508 (10) 0.0512 (7)
H34 0.215362 1.024354 0.161223 0.061*
C35 −0.0111 (4) 1.0121 (3) 0.19741 (10) 0.0463 (7)
H35 −0.027019 1.09415 0.214785 0.056*
C36 −0.2919 (4) 0.9871 (4) 0.23973 (10) 0.0478 (7)
C37 0.4280 (5) 0.8751 (5) 0.09807 (14) 0.0885 (12)
H37A 0.483742 0.868761 0.128435 0.106*
H37B 0.369923 0.984835 0.085011 0.106*
C38 0.5698 (6) 0.7907 (7) 0.06316 (18) 0.153 (2)
H38A 0.667443 0.830217 0.059976 0.229*
H38B 0.515701 0.807254 0.032204 0.229*
H38C 0.617246 0.680406 0.074893 0.229*
H31N 0.778 (5) 0.425 (6) 0.2007 (14) 0.183*
H32N 0.677 (7) 0.324 (3) 0.2290 (18) 0.183*
H61N 0.407 (4) 1.009 (5) 0.2766 (18) 0.183*
H62N 0.236 (6) 1.131 (5) 0.2599 (12) 0.183*

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0514 (15) 0.173 (3) 0.0801 (19) −0.0138 (17) 0.0103 (14) 0.0040 (18)
O2 0.0855 (17) 0.129 (2) 0.0445 (15) −0.0320 (16) 0.0107 (13) −0.0023 (14)
N3 0.0550 (18) 0.076 (2) 0.0573 (19) −0.0143 (15) 0.0078 (15) −0.0036 (15)
N1 0.0399 (13) 0.0448 (14) 0.0380 (13) −0.0148 (11) −0.0030 (10) −0.0033 (11)
N2 0.0450 (14) 0.0536 (16) 0.0466 (15) −0.0175 (13) 0.0038 (11) −0.0089 (13)
C1 0.0440 (16) 0.0302 (15) 0.0369 (16) −0.0153 (13) −0.0019 (13) −0.0053 (12)
C2 0.0486 (17) 0.0463 (17) 0.0378 (16) −0.0152 (14) −0.0064 (14) −0.0001 (13)
C3 0.0392 (16) 0.0525 (19) 0.0513 (19) −0.0132 (14) −0.0007 (14) −0.0071 (15)
C4 0.0488 (18) 0.0463 (18) 0.0441 (18) −0.0167 (15) 0.0066 (14) −0.0065 (14)
C5 0.0584 (19) 0.0406 (17) 0.0386 (16) −0.0186 (15) −0.0016 (14) −0.0020 (13)
C6 0.0433 (16) 0.0381 (16) 0.0457 (17) −0.0127 (13) −0.0066 (14) −0.0027 (13)
C7 0.0407 (16) 0.0543 (18) 0.0470 (18) −0.0162 (14) −0.0043 (13) −0.0088 (14)
C8 0.0440 (17) 0.066 (2) 0.057 (2) −0.0243 (15) 0.0013 (15) −0.0150 (16)
C9 0.0544 (18) 0.0547 (19) 0.0451 (18) −0.0186 (16) 0.0029 (14) 0.0005 (14)
C10 0.0452 (17) 0.068 (2) 0.0392 (17) −0.0168 (15) −0.0010 (13) −0.0005 (15)
O3 0.0458 (12) 0.0732 (15) 0.0477 (12) −0.0181 (11) 0.0023 (10) 0.0009 (11)
O4 0.0585 (12) 0.0634 (13) 0.0375 (12) −0.0259 (11) 0.0003 (9) 0.0022 (10)
O5 0.0505 (13) 0.0959 (17) 0.0504 (13) −0.0107 (12) 0.0086 (11) 0.0129 (12)
C11 0.0480 (17) 0.0392 (16) 0.0352 (15) −0.0199 (14) 0.0001 (13) −0.0026 (13)
C12 0.0524 (18) 0.064 (2) 0.0362 (16) −0.0234 (16) −0.0022 (14) 0.0074 (14)
C13 0.0453 (17) 0.072 (2) 0.0455 (19) −0.0155 (16) −0.0029 (15) 0.0053 (16)
C14 0.0489 (18) 0.060 (2) 0.0424 (18) −0.0173 (16) 0.0060 (15) −0.0001 (15)
C15 0.056 (2) 0.075 (2) 0.0327 (17) −0.0089 (17) 0.0009 (15) 0.0090 (15)
C16 0.0458 (17) 0.0560 (19) 0.0431 (18) −0.0091 (15) −0.0006 (14) 0.0016 (15)
C17 0.0498 (18) 0.0416 (17) 0.0418 (18) −0.0237 (15) 0.0000 (14) −0.0054 (14)
C18 0.050 (2) 0.106 (3) 0.069 (2) −0.014 (2) 0.0095 (17) 0.007 (2)
C19 0.058 (2) 0.154 (4) 0.088 (3) −0.011 (2) 0.022 (2) 0.011 (3)
O6 0.125 (3) 0.136 (3) 0.0580 (18) −0.028 (2) 0.0049 (16) 0.0186 (18)
O7 0.099 (2) 0.208 (3) 0.0619 (18) −0.070 (2) 0.0107 (15) −0.049 (2)
N6 0.0584 (19) 0.129 (3) 0.049 (2) −0.022 (2) 0.0005 (15) −0.010 (2)
N4 0.0744 (17) 0.0449 (14) 0.0381 (14) −0.0343 (13) −0.0005 (12) −0.0046 (11)
N5 0.0553 (15) 0.0425 (15) 0.0435 (14) −0.0231 (12) 0.0049 (12) −0.0033 (12)
C20 0.0459 (16) 0.0463 (18) 0.0443 (18) −0.0147 (14) 0.0001 (13) −0.0083 (14)
C21 0.099 (3) 0.054 (2) 0.0440 (19) −0.0301 (19) 0.0055 (17) −0.0063 (16)
C22 0.101 (3) 0.070 (2) 0.047 (2) −0.031 (2) 0.0048 (19) 0.0032 (18)
C23 0.0510 (19) 0.091 (3) 0.0396 (19) −0.0177 (19) −0.0027 (15) −0.0030 (19)
C24 0.087 (3) 0.110 (3) 0.051 (2) −0.041 (2) 0.0054 (19) −0.038 (2)
C25 0.099 (3) 0.074 (2) 0.059 (2) −0.049 (2) 0.0046 (19) −0.0196 (19)
C26 0.071 (2) 0.058 (2) 0.0524 (19) −0.0381 (17) 0.0000 (16) −0.0085 (16)
C27 0.072 (2) 0.0427 (17) 0.0533 (19) −0.0303 (16) 0.0104 (16) −0.0060 (15)
C28 0.0607 (19) 0.0526 (18) 0.0439 (18) −0.0310 (16) 0.0008 (14) −0.0043 (14)
C29 0.077 (2) 0.0475 (18) 0.0436 (18) −0.0344 (16) −0.0019 (15) −0.0032 (14)
O8 0.0597 (13) 0.0531 (13) 0.0781 (15) −0.0273 (11) 0.0142 (11) −0.0062 (11)
O9 0.0627 (13) 0.0524 (13) 0.0573 (13) −0.0226 (11) 0.0088 (10) −0.0129 (11)
O10 0.0744 (15) 0.0862 (17) 0.0732 (16) −0.0304 (14) 0.0256 (13) −0.0281 (13)
C30 0.0447 (16) 0.0366 (16) 0.0382 (16) −0.0133 (13) −0.0061 (13) 0.0021 (13)
C31 0.0524 (18) 0.0469 (18) 0.0559 (19) −0.0229 (15) −0.0043 (15) −0.0020 (15)
C32 0.064 (2) 0.0469 (18) 0.056 (2) −0.0192 (16) −0.0013 (16) −0.0139 (15)
C33 0.0507 (18) 0.0488 (18) 0.0463 (18) −0.0113 (15) 0.0020 (14) −0.0032 (15)
C34 0.0482 (17) 0.0498 (19) 0.058 (2) −0.0232 (15) 0.0023 (15) −0.0036 (16)
C35 0.0490 (17) 0.0437 (17) 0.0490 (18) −0.0186 (14) −0.0048 (14) −0.0077 (14)
C36 0.0480 (18) 0.0481 (19) 0.0442 (18) −0.0162 (15) −0.0073 (14) 0.0022 (15)
C37 0.075 (3) 0.110 (3) 0.082 (3) −0.040 (2) 0.025 (2) −0.014 (2)
C38 0.122 (4) 0.205 (6) 0.147 (5) −0.072 (4) 0.083 (4) −0.079 (4)

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Geometric parameters (Å, º)

O1—N3 1.220 (3) O6—N6 1.231 (4)
O2—N3 1.213 (3) O7—N6 1.223 (4)
N3—C4 1.447 (3) N6—C23 1.456 (4)
N1—C1 1.384 (3) N4—C20 1.378 (3)
N1—C7 1.462 (3) N4—C26 1.449 (3)
N1—C10 1.467 (3) N4—C29 1.452 (3)
N2—C9 1.475 (3) N5—C27 1.476 (4)
N2—C8 1.481 (4) N5—C28 1.486 (3)
N2—H31N 0.937 (19) N5—H61N 0.910 (19)
N2—H32N 0.895 (19) N5—H62N 0.896 (19)
C1—C2 1.405 (3) C20—C21 1.384 (4)
C1—C6 1.412 (3) C20—C25 1.391 (4)
C2—C3 1.366 (4) C21—C22 1.370 (4)
C2—H2 0.93 C21—H21 0.93
C3—C4 1.376 (4) C22—C23 1.349 (4)
C3—H3 0.93 C22—H22 0.93
C4—C5 1.377 (4) C23—C24 1.359 (5)
C5—C6 1.372 (3) C24—C25 1.381 (4)
C5—H5 0.93 C24—H24 0.93
C6—H6 0.93 C25—H25 0.93
C7—C8 1.498 (3) C26—C27 1.497 (4)
C7—H7A 0.97 C26—H26A 0.97
C7—H7B 0.97 C26—H26B 0.97
C8—H8A 0.97 C27—H27A 0.97
C8—H8B 0.97 C27—H27B 0.97
C9—C10 1.493 (3) C28—C29 1.498 (4)
C9—H9A 0.97 C28—H28A 0.97
C9—H9B 0.97 C28—H28B 0.97
C10—H10A 0.97 C29—H29A 0.97
C10—H10B 0.97 C29—H29B 0.97
O3—C17 1.261 (3) O8—C36 1.264 (3)
O4—C17 1.253 (3) O9—C36 1.252 (3)
O5—C14 1.365 (3) O10—C33 1.363 (3)
O5—C18 1.426 (3) O10—C37 1.431 (4)
C11—C12 1.375 (4) C30—C35 1.372 (3)
C11—C16 1.383 (3) C30—C31 1.387 (4)
C11—C17 1.499 (4) C30—C36 1.500 (4)
C12—C13 1.379 (4) C31—C32 1.376 (4)
C12—H12 0.93 C31—H31 0.93
C13—C14 1.373 (4) C32—C33 1.383 (4)
C13—H13 0.93 C32—H32 0.93
C14—C15 1.378 (4) C33—C34 1.381 (4)
C15—C16 1.374 (4) C34—C35 1.378 (4)
C15—H15 0.93 C34—H34 0.93
C16—H16 0.93 C35—H35 0.93
C18—C19 1.502 (4) C37—C38 1.496 (5)
C18—H18A 0.97 C37—H37A 0.97
C18—H18B 0.97 C37—H37B 0.97
C19—H19A 0.96 C38—H38A 0.96
C19—H19B 0.96 C38—H38B 0.96
C19—H19C 0.96 C38—H38C 0.96
O2—N3—O1 122.7 (3) O7—N6—O6 123.5 (4)
O2—N3—C4 119.3 (3) O7—N6—C23 118.2 (4)
O1—N3—C4 118.0 (3) O6—N6—C23 118.2 (4)
C1—N1—C7 118.1 (2) C20—N4—C26 121.3 (2)
C1—N1—C10 117.0 (2) C20—N4—C29 121.3 (2)
C7—N1—C10 116.3 (2) C26—N4—C29 111.9 (2)
C9—N2—C8 107.9 (2) C27—N5—C28 110.0 (2)
C9—N2—H31N 110 (3) C27—N5—H61N 112 (3)
C8—N2—H31N 108 (3) C28—N5—H61N 110 (3)
C9—N2—H32N 111 (3) C27—N5—H62N 108 (3)
C8—N2—H32N 106 (3) C28—N5—H62N 110 (3)
H31N—N2—H32N 113 (4) H61N—N5—H62N 107 (4)
N1—C1—C2 120.9 (2) N4—C20—C21 121.8 (3)
N1—C1—C6 122.0 (2) N4—C20—C25 122.0 (3)
C2—C1—C6 117.1 (2) C21—C20—C25 116.2 (3)
C3—C2—C1 121.3 (3) C22—C21—C20 121.6 (3)
C3—C2—H2 119.3 C22—C21—H21 119.2
C1—C2—H2 119.3 C20—C21—H21 119.2
C2—C3—C4 120.1 (3) C23—C22—C21 120.9 (3)
C2—C3—H3 120 C23—C22—H22 119.6
C4—C3—H3 120 C21—C22—H22 119.6
C3—C4—C5 120.6 (3) C22—C23—C24 119.7 (3)
C3—C4—N3 119.6 (3) C22—C23—N6 120.8 (4)
C5—C4—N3 119.8 (3) C24—C23—N6 119.5 (4)
C6—C5—C4 119.8 (3) C23—C24—C25 119.9 (3)
C6—C5—H5 120.1 C23—C24—H24 120
C4—C5—H5 120.1 C25—C24—H24 120
C5—C6—C1 121.2 (3) C24—C25—C20 121.6 (3)
C5—C6—H6 119.4 C24—C25—H25 119.2
C1—C6—H6 119.4 C20—C25—H25 119.2
N1—C7—C8 113.3 (2) N4—C26—C27 110.5 (2)
N1—C7—H7A 108.9 N4—C26—H26A 109.5
C8—C7—H7A 108.9 C27—C26—H26A 109.5
N1—C7—H7B 108.9 N4—C26—H26B 109.5
C8—C7—H7B 108.9 C27—C26—H26B 109.5
H7A—C7—H7B 107.7 H26A—C26—H26B 108.1
N2—C8—C7 110.9 (2) N5—C27—C26 111.0 (2)
N2—C8—H8A 109.5 N5—C27—H27A 109.4
C7—C8—H8A 109.5 C26—C27—H27A 109.4
N2—C8—H8B 109.5 N5—C27—H27B 109.4
C7—C8—H8B 109.5 C26—C27—H27B 109.4
H8A—C8—H8B 108 H27A—C27—H27B 108
N2—C9—C10 111.5 (2) N5—C28—C29 111.1 (2)
N2—C9—H9A 109.3 N5—C28—H28A 109.4
C10—C9—H9A 109.3 C29—C28—H28A 109.4
N2—C9—H9B 109.3 N5—C28—H28B 109.4
C10—C9—H9B 109.3 C29—C28—H28B 109.4
H9A—C9—H9B 108 H28A—C28—H28B 108
N1—C10—C9 113.7 (2) N4—C29—C28 111.5 (2)
N1—C10—H10A 108.8 N4—C29—H29A 109.3
C9—C10—H10A 108.8 C28—C29—H29A 109.3
N1—C10—H10B 108.8 N4—C29—H29B 109.3
C9—C10—H10B 108.8 C28—C29—H29B 109.3
H10A—C10—H10B 107.7 H29A—C29—H29B 108
C14—O5—C18 118.3 (2) C33—O10—C37 118.5 (3)
C12—C11—C16 117.5 (2) C35—C30—C31 117.1 (3)
C12—C11—C17 120.9 (2) C35—C30—C36 120.9 (3)
C16—C11—C17 121.6 (3) C31—C30—C36 122.0 (2)
C11—C12—C13 122.1 (3) C32—C31—C30 121.5 (3)
C11—C12—H12 119 C32—C31—H31 119.2
C13—C12—H12 119 C30—C31—H31 119.2
C14—C13—C12 119.5 (3) C31—C32—C33 120.0 (3)
C14—C13—H13 120.3 C31—C32—H32 120
C12—C13—H13 120.3 C33—C32—H32 120
O5—C14—C13 124.4 (3) O10—C33—C34 124.5 (3)
O5—C14—C15 116.1 (3) O10—C33—C32 116.1 (3)
C13—C14—C15 119.5 (3) C34—C33—C32 119.4 (3)
C16—C15—C14 120.2 (3) C35—C34—C33 119.2 (3)
C16—C15—H15 119.9 C35—C34—H34 120.4
C14—C15—H15 119.9 C33—C34—H34 120.4
C15—C16—C11 121.2 (3) C30—C35—C34 122.7 (3)
C15—C16—H16 119.4 C30—C35—H35 118.6
C11—C16—H16 119.4 C34—C35—H35 118.6
O4—C17—O3 123.5 (2) O9—C36—O8 124.0 (3)
O4—C17—C11 119.3 (3) O9—C36—C30 118.3 (3)
O3—C17—C11 117.3 (2) O8—C36—C30 117.7 (3)
O5—C18—C19 107.3 (3) O10—C37—C38 107.4 (3)
O5—C18—H18A 110.3 O10—C37—H37A 110.2
C19—C18—H18A 110.3 C38—C37—H37A 110.2
O5—C18—H18B 110.3 O10—C37—H37B 110.2
C19—C18—H18B 110.3 C38—C37—H37B 110.2
H18A—C18—H18B 108.5 H37A—C37—H37B 108.5
C18—C19—H19A 109.5 C37—C38—H38A 109.5
C18—C19—H19B 109.5 C37—C38—H38B 109.5
H19A—C19—H19B 109.5 H38A—C38—H38B 109.5
C18—C19—H19C 109.5 C37—C38—H38C 109.5
H19A—C19—H19C 109.5 H38A—C38—H38C 109.5
H19B—C19—H19C 109.5 H38B—C38—H38C 109.5
C7—N1—C1—C2 −173.1 (2) C26—N4—C20—C21 −149.7 (3)
C10—N1—C1—C2 −26.5 (3) C29—N4—C20—C21 2.0 (4)
C7—N1—C1—C6 8.5 (3) C26—N4—C20—C25 33.3 (4)
C10—N1—C1—C6 155.0 (2) C29—N4—C20—C25 −175.1 (3)
N1—C1—C2—C3 −177.9 (2) N4—C20—C21—C22 −174.3 (3)
C6—C1—C2—C3 0.6 (4) C25—C20—C21—C22 2.8 (5)
C1—C2—C3—C4 −0.7 (4) C20—C21—C22—C23 −1.3 (5)
C2—C3—C4—C5 0.3 (4) C21—C22—C23—C24 −0.7 (5)
C2—C3—C4—N3 −178.7 (3) C21—C22—C23—N6 177.8 (3)
O2—N3—C4—C3 −170.8 (3) O7—N6—C23—C22 −179.8 (3)
O1—N3—C4—C3 9.6 (4) O6—N6—C23—C22 −3.4 (5)
O2—N3—C4—C5 10.2 (4) O7—N6—C23—C24 −1.3 (5)
O1—N3—C4—C5 −169.4 (3) O6—N6—C23—C24 175.1 (3)
C3—C4—C5—C6 0.2 (4) C22—C23—C24—C25 0.9 (5)
N3—C4—C5—C6 179.2 (3) N6—C23—C24—C25 −177.6 (3)
C4—C5—C6—C1 −0.2 (4) C23—C24—C25—C20 0.8 (5)
N1—C1—C6—C5 178.3 (2) N4—C20—C25—C24 174.6 (3)
C2—C1—C6—C5 −0.2 (4) C21—C20—C25—C24 −2.6 (5)
C1—N1—C7—C8 −173.0 (2) C20—N4—C26—C27 −148.9 (3)
C10—N1—C7—C8 40.3 (3) C29—N4—C26—C27 57.0 (3)
C9—N2—C8—C7 62.2 (3) C28—N5—C27—C26 56.4 (3)
N1—C7—C8—N2 −51.8 (3) N4—C26—C27—N5 −57.5 (3)
C8—N2—C9—C10 −61.5 (3) C27—N5—C28—C29 −54.8 (3)
C1—N1—C10—C9 173.4 (2) C20—N4—C29—C28 150.1 (2)
C7—N1—C10—C9 −39.5 (3) C26—N4—C29—C28 −55.8 (3)
N2—C9—C10—N1 50.3 (3) N5—C28—C29—N4 54.6 (3)
C16—C11—C12—C13 0.5 (4) C35—C30—C31—C32 −1.0 (4)
C17—C11—C12—C13 −177.6 (3) C36—C30—C31—C32 177.1 (3)
C11—C12—C13—C14 0.4 (5) C30—C31—C32—C33 1.6 (4)
C18—O5—C14—C13 1.3 (5) C37—O10—C33—C34 0.7 (4)
C18—O5—C14—C15 −178.7 (3) C37—O10—C33—C32 −178.7 (3)
C12—C13—C14—O5 178.9 (3) C31—C32—C33—O10 178.6 (3)
C12—C13—C14—C15 −1.0 (5) C31—C32—C33—C34 −0.8 (4)
O5—C14—C15—C16 −179.2 (3) O10—C33—C34—C35 −179.8 (3)
C13—C14—C15—C16 0.7 (5) C32—C33—C34—C35 −0.5 (4)
C14—C15—C16—C11 0.2 (5) C31—C30—C35—C34 −0.3 (4)
C12—C11—C16—C15 −0.8 (4) C36—C30—C35—C34 −178.5 (3)
C17—C11—C16—C15 177.3 (3) C33—C34—C35—C30 1.1 (4)
C12—C11—C17—O4 2.7 (4) C35—C30—C36—O9 15.2 (4)
C16—C11—C17—O4 −175.3 (2) C31—C30—C36—O9 −162.9 (3)
C12—C11—C17—O3 −177.3 (3) C35—C30—C36—O8 −166.4 (2)
C16—C11—C17—O3 4.6 (4) C31—C30—C36—O8 15.5 (4)
C14—O5—C18—C19 178.7 (3) C33—O10—C37—C38 176.2 (3)

4-(4-Nitrophenyl)piperazin-1-ium 4-ethoxybenzoate (VI). Hydrogen-bond geometry (Å, º)

Cg2 and Cg6 are the centroids of the C1–C6 and C30–C35 rings, respectively.

D—H···A D—H H···A D···A D—H···A
N2—H31N···O3i 0.94 (2) 1.68 (2) 2.613 (3) 172 (5)
N2—H31N···O4i 0.94 (2) 2.51 (4) 3.157 (3) 127 (4)
N2—H32N···O9ii 0.90 (2) 1.96 (2) 2.843 (3) 171 (5)
N5—H61N···O8i 0.91 (2) 1.78 (2) 2.686 (3) 175 (5)
N5—H61N···O9i 0.91 (2) 2.59 (4) 3.174 (3) 122 (4)
N5—H62N···O4iii 0.90 (2) 1.83 (2) 2.708 (3) 165 (5)
C22—H22···O2iv 0.93 2.6 3.502 (5) 165
C27—H27B···O9i 0.97 2.59 3.215 (3) 123
C28—H28B···O7v 0.97 2.65 3.410 (4) 135
C29—H29B···O1i 0.97 2.53 3.249 (4) 131
C35—H35···O4iii 0.93 2.52 3.263 (3) 137
C10—H10A···Cg6 0.97 2.82 3.746 (3) 159
C29—H29A···Cg2 0.97 2.76 3.556 (3) 139

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

Funding Statement

NM is grateful to the University of Mysore for research facilities. HSY thanks the UGC for a BSR Faculty fellowship for three years. SGG gratefully acknowledges financial support from the Spanish Ministerio de Ciencia e Innovación (PID2020–113558RB-C41) and Gobierno del Principado de Asturias (AYUD/2021/50997).

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I, II, III, IV, V, VI. DOI: 10.1107/S2056989022004157/ex2056sup1.cif

e-78-00510-sup1.cif (2.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022004157/ex2056Isup2.hkl

e-78-00510-Isup2.hkl (281.4KB, hkl)

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989022004157/ex2056IIsup3.hkl

e-78-00510-IIsup3.hkl (280.3KB, hkl)

Structure factors: contains datablock(s) III. DOI: 10.1107/S2056989022004157/ex2056IIIsup4.hkl

e-78-00510-IIIsup4.hkl (250.4KB, hkl)

Structure factors: contains datablock(s) IV. DOI: 10.1107/S2056989022004157/ex2056IVsup5.hkl

e-78-00510-IVsup5.hkl (266.8KB, hkl)

Structure factors: contains datablock(s) V. DOI: 10.1107/S2056989022004157/ex2056Vsup6.hkl

e-78-00510-Vsup6.hkl (533.7KB, hkl)

Structure factors: contains datablock(s) VI. DOI: 10.1107/S2056989022004157/ex2056VIsup7.hkl

e-78-00510-VIsup7.hkl (544.9KB, hkl)

CCDC references: 2167424, 2167423, 2167422, 2167421, 2167420, 2167419

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


Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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