Syntheses and crystal structures of four 4-(4-nitro­phen­yl)piperazinium salts with hydrogen succinate, 4-amino­benzoate, 2-(4-chloro­phen­yl)acetate and 2,3,4,5,6-penta­fluoro­benzoate anions

Vinaya; Basavaraju, Y.B.; Yathirajan, H.S.; Parkin, S.

doi:10.1107/S2056989023001093

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 79| Part 3| March 2023| Pages 151-156

https://doi.org/10.1107/S2056989023001093

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Syntheses and crystal structures of four 4-(4-nitrophenyl)piperazinium salts with hydrogen succinate, 4-aminobenzoate, 2-(4-chlorophenyl)acetate and 2,3,4,5,6-pentafluorobenzoate anions

Vinaya,^a Yeriyur B. Basavaraju,^a ^* Hemmige S. Yathirajan ^a ^* and Sean Parkin ^b

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, and ^bDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
^*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 3 February 2023; accepted 4 February 2023; online 9 February 2023)

The syntheses and crystal structures are presented for four organic salts of the 4-(4-nitrophenyl)piperazinium cation, namely, 4-(4-nitrophenyl)piperazinium hydrogen succinate, C₁₀H₁₄N₃O₂⁺·C₄H₅O₄⁻ (I), 4-(4-nitrophenyl)piperazinium 4-aminobenzoate monohydrate, C₁₀H₁₄N₃O₂⁺·C₇H₆NO₂⁻·H₂O (II), 4-(4-nitrophenyl)piperazinium 2-(4-chlorophenyl)acetate, C₁₀H₁₄N₃O₂⁺·C₈H₆ClO₂⁻ (III) and 4-(4-nitrophenyl)piperazinium 2,3,4,5,6-pentafluorobenzoate, C₁₀H₁₄N₃O₂⁺·C₇F₅O₂⁻ (IV). The salts form from mixtures of N-(4-nitrophenyl)piperazine and the corresponding acid [succinic acid (I), 4-aminobenzoic acid (II), 2-(4-chlorophenyl)acetic acid (III) and 2,3,4,5,6-pentafluorobenzoic acid (IV)] in mixed solvents of methanol and ethyl acetate. Salts I, III, and IV are anhydrous, whereas II is a monohydrate. In each structure, the overall conformation of the cation is determined by the disposition of the exocyclic N—C bond of the piperazine ring (either axial or equatorial) and twists about the N—C bond between the piperazine ring and its attached 4-nitrophenyl ring. The packing motifs in each structure are quite different, though all are dominated by strong N—H⋯O hydrogen bonds, which are augmented in I and II by O—H⋯O hydrogen bonds, and in III by a π–π stacking interaction between inversion-related 4-nitrophenyl groups.

Keywords: crystal structure; piperazinium salt; symmetrical hydrogen bond; crystal structure.

CCDC references: 2239906; 2239905; 2239904; 2239903

1. Chemical context

4-Nitrophenylpiperazinium chloride monohydrate has been used as an intermediate in the synthesis of anticancer drugs, transcriptase inhibitors and antifungal reagents (Berkheij et al., 2005 ; Chaudhary et al., 2006 ; Kharb et al., 2012 ; Upadhayaya et al., 2004 ). It is also an important reagent for potassium channel openers, which show significant biomolecular current-voltage rectification characteristics (Lu, 2007 ). The design, synthesis and biological profiling of arylpiperazine-based scaffolds for the management of androgen-sensitive prostatic disorders was described by Gupta et al. (2016 ). 4-Nitrophenylpiperazine was the starting material in the synthesis and biological evaluation of new piperazine-containing hydrazone derivatives (Kaya et al., 2016 ). A review on the piperazine skeleton in the structural modification of natural products was recently published by Zhang et al. (2021 ).

As part of our studies in this area, this paper describes the crystal structures of four salts of 4-nitrophenylpiperazine with organic acids, viz, 4-(4-nitrophenyl)piperazinium hydrogen succinate, C₁₀H₁₄N₃O₂⁺·C₄H₅O₄⁻ (I), 4-(4-nitrophenyl)piperazinium 4-aminobenzoate monohydrate, C₁₀H₁₄N₃O₂⁺·C₇H₆NO₂⁻·H₂O (II), 4-(4-nitrophenyl)piperazinium 2-(4-chlorophenyl)acetate, C₁₀H₁₄N₃O₂⁺·C₈H₆ClO₂⁻ (III) and 4-(4-nitrophenyl)piperazinium 2,3,4,5,6-pentafluorobenzoate, C₁₀H₁₄N₃O₂⁺·C₇F₅O₂⁻ (IV).

2. Structural commentary

The overall conformations of the 4-nitrophenylpiperazinium cations in I–IV are determined by the N2—C5 bonds, which link the 4-nitrophenyl and piperazinium rings (Figs. 1–4 ). Within each structure, atom N2 is non-planar, the sums of bond angles being 352.73 (16)° (I), 344.91 (12)° (II), 348.75 (15)° (III), and 348.85 (17)° (IV), so the connection of the exocyclic carbon atom is either equatorial (II, III) or axial (I, IV). The relative twist about these N2—C5 bonds, e.g. quantified by the C2—N2—C5—C6 torsional angles [–168.06 (10)° for I, 149.97 (9)° for II, 167.32 (10)° for III, and −170.03 (10)° for IV] determine the overall cation shape. In each case, the 4-nitro group is essentially coplanar with its attached phenyl ring.

Figure 1
The molecular structure (50% displacement ellipsoids) of I. Hydrogen atoms are shown as arbitrary circles. The dashed line indicates a hydrogen bond.

Figure 2
The molecular structure (50% displacement ellipsoids) of II. Hydrogen atoms are shown as arbitrary circles. The dashed lines indicate hydrogen bonds.

Figure 3
The molecular structure (50% displacement ellipsoids) of III. Hydrogen atoms are shown as arbitrary circles. The dashed line indicates a hydrogen bond.

Figure 4
The molecular structure (50% displacement ellipsoids) of IV. Hydrogen atoms are shown as arbitrary circles. The dashed line indicates a hydrogen bond.

The succinate anion in I has minor twists about its three C—C bonds [torsion angles 165.46 (9), 166.06 (8), and 169.97 (9)° for O4—C11—C12—C13, C11—C12—C13—C14, and C12—C13—C14—O6, respectively], which leads to a dihedral angle of 34.63 (9)° between its carboxylate/carboxylic acid groups. The 4-aminobenzoate anion of II is close to planar, having a dihedral angle between the carboxylate group and its benzene ring of 10.70 (7)°. The amine group at N4 is also slightly non-planar [the sum of angles about N4 is 349 (2)°]. In the 2-(4-chlorophenyl)acetate anion of III, twists about the C11—C12 and C12—C13 bonds place the carboxylate group almost perpendicular [85.02 (9)°] to the benzene ring. Lastly, in the pentafluorobenzoate anion of IV, the carboxylate group is 55.95 (10)° out of coplanarity with the phenyl ring.

Throughout all four structures, individual bond lengths and angles take on normal values except for an elongated O—H bond [1.17 (2) Å] in I, which will be described in more detail in the next section (Supramolecular features).

3. Supramolecular features

Hydrogen bonding plays a significant role in the packing of all four salts (see Tables 1–4 ). In each structure, the asymmetric units were chosen to give the shortest hydrogen bonds between the cationic NH₂ group and the anionic carboxylate groups. In I, II, and IV, these hydrogen bonds to the anion are equatorial relative to the piperazine ring, while that in III is axial. Nevertheless, in each structure, the NH₂⁺ group acts as a hydrogen-bond donor through both its hydrogen atoms. In I, III, and IV this is to a second anion, whereas in II it is to the included water molecule. Throughout the four structures, all conventional N—H⋯O and all but one O—H⋯O (in I, vide infra) hydrogen bonds take on normal distances and angles (Tables 1–4 ).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O3	0.934 (15)	1.793 (16)	2.7250 (12)	175.5 (13)
N1—H1NB⋯O5ⁱ	0.903 (16)	1.945 (16)	2.8127 (12)	160.5 (13)
O6—H6O⋯O4ⁱⁱ	1.17 (2)	1.27 (2)	2.4367 (10)	176 (2)
C1—H1A⋯O6ⁱⁱⁱ	0.99	2.49	3.1374 (13)	123
C3—H3A⋯O5ⁱ	0.99	2.59	3.3238 (15)	130
C3—H3B⋯O2^iv	0.99	2.51	3.4168 (15)	153
C4—H4A⋯O2^v	0.99	2.55	3.5053 (15)	162
C4—H4B⋯O4^vi	0.99	2.45	3.2354 (13)	136
C10—H10⋯O4^vii	0.95	2.57	3.4146 (13)	149
Symmetry codes: (i) $[-x+1, y+1, -z+{\script{1\over 2}}]$ ; (ii) ; (iii) x, y+1, z; (iv) $[x, -y+2, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (vi) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (vii) .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O3	0.936 (17)	1.804 (17)	2.737 (1)	174.7 (15)
N1—H1NB⋯O1Wⁱ	0.942 (15)	1.864 (15)	2.7934 (11)	168.4 (13)
N4—H4NA⋯O1ⁱⁱ	0.879 (18)	2.258 (18)	3.0861 (13)	156.9 (15)
N4—H4NB⋯O2ⁱⁱⁱ	0.886 (18)	2.248 (17)	3.0315 (13)	147.3 (14)
O1W—H1W1⋯O3^iv	0.877 (18)	1.890 (18)	2.7569 (11)	169.7 (16)
O1W—H2W1⋯O4	0.885 (18)	1.755 (18)	2.6388 (11)	177.2 (17)
C1—H1C⋯O1W	0.99	2.50	3.2511 (12)	132
C2—H2B⋯O4ⁱ	0.99	2.58	3.5572 (13)	170
C4—H4A⋯O3^v	0.99	2.51	3.4578 (12)	161
C4—H4B⋯O1W^vi	0.99	2.53	3.2921 (12)	134
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) x+1, y, z.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O4ⁱ	0.894 (16)	1.848 (16)	2.7252 (12)	166.3 (14)
N1—H1NB⋯O3	0.937 (16)	1.765 (17)	2.6903 (12)	169.0 (15)
C4—H4A⋯O4ⁱⁱ	0.99	2.46	3.2539 (14)	137
C7—H7⋯O1ⁱⁱⁱ	0.95	2.59	3.2256 (15)	124
C12—H12A⋯O3^iv	0.99	2.49	3.4710 (14)	173
C15—H15⋯O2^v	0.95	2.37	3.1944 (15)	146
C18—H18⋯O3^vi	0.95	2.55	3.2644 (15)	132
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) x+1, y, z.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NA⋯O3	0.929 (15)	1.754 (16)	2.6723 (13)	169.4 (14)
N1—H1NB⋯O4ⁱ	0.915 (16)	1.816 (16)	2.7310 (13)	178.8 (14)
C1—H1C⋯F5ⁱⁱ	0.99	2.49	3.4813 (14)	177
C1—H1D⋯F4ⁱⁱⁱ	0.99	2.49	3.3996 (14)	153
C4—H4B⋯O3^iv	0.99	2.56	3.3421 (15)	136
C6—H6⋯F2^v	0.95	2.54	3.4536 (15)	161
Symmetry codes: (i) x+1, y, z; (ii) ; (iii) ; (iv) ; (v) .

The structure of I includes an unusually short O6—H6⋯O4(x, y − 1, z) hydrogen bond [O⋯O = 2.4367 (10) Å], which links adjacent hydrogen-succinate anions into chains that propagate parallel to the b-axis direction (Fig. 5). Difference map density for this hydrogen (H6) appears roughly equidistant from both oxygen atoms (Fig. 6), and refines to give O6—H6 = 1.17 (2) Å (Table 1). For unusually strong hydrogen bonds, the migration of the hydrogen atom towards the midpoint between the donor and acceptor atoms is an expected phenomenon. In such instances, the case for positional refinement of the hydrogen atom, or even placement at the difference map peak coordinates is compelling (Fábry, 2018 ), and is backed by density-functional theory computational analysis (see e.g. Bhardwaj et al., 2020 ). A number of weak C—H⋯O interactions also occur.

Figure 5
A partial packing plot of I showing extended double chains of O—H⋯O hydrogen-bonded (dotted lines) succinate anions, linked via N—H⋯O hydrogen bonds to the 4-nitrophenylpiperazinium cations. Hydrogen atoms not involved in hydrogen bonds are omitted.

Figure 6
Difference-Fourier electron-density map for the region of the hydrogen atom situated close to the donor–acceptor midpoint in the short O—H⋯O hydrogen bond [thin black line, O⋯O = 2.4367 (1) Å] linking the hydrogen succinate cations into chains propagating parallel to the b-axis in I.

Structure II also includes N—H⋯O hydrogen bonds from the 4-amino group of its anion to the nitro oxygen atoms of its cation (Table 2). The cation–anion interactions, along with the presence of the water molecule, which acts as an O—H⋯O hydrogen-bond donor to join a pair of translation-related (1 + x, y, z) anions and as an acceptor for an N—H⋯O hydrogen bond, generates a double-layer network lying parallel to (011) (Fig. 7). Of the four structures, II has the most complex hydrogen-bonding interactions.

Figure 7
A partial packing plot of II showing N—H⋯O and O—H⋯O hydrogen-bonded (dotted lines) double layers that extend parallel to (011). Hydrogen atoms not involved in hydrogen bonds are omitted.

The primary supramolecular interaction in III joins two pairs of inversion-related ammonium cations and carboxylate anions, forming an R₄⁴(12) ring motif (Table 3, Fig. 8). Structure III also includes the only π–π interactions of the four structures, which occurs between inversion-related (−x, 1 − y, −z) nitrophenyl rings, giving an interplanar spacing of 3.3352 (15) Å, though the offset (≃1.92 Å) is large, leading to a centroid–centroid distance of 3.8495 (15) Å (Fig. 8, dashed line).

Figure 8
A partial packing plot of III showing a hydrogen-bonded (dotted lines) R₄⁴(12) ring motif and a π–π interaction (dashed line) between inversion-related cations. Hydrogen atoms not involved in hydrogen bonds are omitted.

Supramolecular interactions within IV are the simplest of the four structures: N—H⋯O hydrogen bonds connect cations and anions into continuous chains that extend parallel to its a-axis. These interactions are quantified in Table 4 and shown in Fig. 9.

Figure 9
A partial packing plot of IV, showing chains of hydrogen-bonded (dotted lines) cations and anions that extend parallel to the a-axis. Hydrogen atoms not involved in hydrogen bonds are omitted.

4. Database survey

A search of the Cambridge Structure Database (CSD v5.43 with updates through September 2022; Groom et al., 2016 ) for salts that include the 4-(4-nitrophenyl)piperazinium cation returned ten hits. Database entries with refcodes LIJNAU (Lu, 2007) and LIJNAU01 (Rehman et al., 2009 ) are monohydrates of the chloride salt. The remaining eight structures, CSD entries NEBVOJ, NEBVUP, NEBWAW, NEBWEA, NEBWIE, NEBWOK (Mahesha et al., 2022 ) and BEFGIG and BEFGOM (Shankara Prasad et al., 2022 ) are all organic salts with a variety of anions, and all but NEBWOK and BEFGOM are hydrates.

Racemic perhydrotriphenylene forms a polar inclusion compound with 1-(4-nitrophenyl)piperazine as a guest molecule (NOVWOK; König et al., 1997 ). The crystal structure of 4,6-dimethoxypyrimidin-2-amine-1-(4-nitrophenyl)piperazine (LUDMUU), was published by Wang et al. (2014 ). The synthesis and crystal structure of a Schiff base, 5-methyl-2-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}phenol (WUWBIC) was published by Ayeni et al. (2019 ). NMR-based investigations by Wodtke et al. (2018 ) of acyl-functionalized piperazines concerning their conformational behavior in solution, included crystal structures of 1-(4-fluorobenzoyl)-4-(4-nitrophenyl)piperazine (BIQYIM), 1-(4-bromobenzoyl)-4-(4-nitrophenyl)piperazine (BIRHES), 1-(3-bromobenzoyl)-4-(4-nitrophenyl)piperazine (BIRHIW) and (piperazine-1,4-diyl)bis[(4-fluorophenyl)methanone] (BIRGOB).

5. Synthesis, crystallization and spectroscopic details

A solution of commercially available (Sigma-Aldrich) 4-nitrophenylpiperazine (100 mg, 0.483 mol) in methanol (10 ml) was mixed with equimolar solutions of the appropriate acid in methanol (10 ml) and ethyl acetate (10 ml) viz., succinic acid (60 mg, 0.483 mol) for I, 4-aminobenzoic acid (69 mg, 0.483 mol) for II, 2-(4-chlorophenyl)acetic acid (85 mg, 0.483 mol) for III, and 2,3,4,5,6-pentafluorobenzoic acid (102 mg, 0.483 mol) for IV. The resulting solutions were stirred for 30 minutes at 333 K and allowed to stand at room temperature. X-ray quality crystals formed on slow evaporation of solutions in ethanol:acetonitrile (1:1) over the course of a week for all four compounds. The melting points are 398–400 K (I), 473–475 K (II), 431–435 K (III) and 411–415 K (IV).

6. Refinement

Crystal data, data collection, and structure refinement details are given in Table 5. All hydrogen atoms were found in difference-Fourier maps, but those bound to carbon were subsequently included in the refinement using riding models, with constrained distances set to 0.95 Å (Csp²—H) and 0.99 Å (R₂CH₂), using U_iso(H) values constrained to 1.2U_eq of the attached carbon atom. All N—H and O—H hydrogen atoms were refined freely (both coordinates and U_iso).

Table 5
Experimental details

	I	II	III	IV
Crystal data
Chemical formula	C₁₀H₁₄N₃O₂⁺·C₄H₅O₄⁻	C₁₀H₁₄N₃O₂⁺·C₇H₆NO₂⁻·H₂O	C₁₀H₁₄N₃O₂⁺·C₈H₆ClO₂⁻	C₁₀H₁₄N₃O₂⁺·C₇F₅O₂⁻
M_r	325.32	362.38	377.82	419.31
Crystal system, space group	Monoclinic, C2/c	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$	Triclinic, P $[\overline{1}]$
Temperature (K)	90	90	90	90
a, b, c (Å)	25.2747 (12), 8.0434 (4), 15.6617 (5)	6.0453 (3), 7.3930 (3), 19.1439 (6)	6.8051 (2), 9.3927 (5), 14.3869 (7)	5.9779 (3), 11.3934 (8), 12.9312 (9)
α, β, γ (°)	90, 105.384 (2), 90	79.482 (2), 89.215 (1), 83.967 (1)	83.849 (2), 81.283 (2), 72.492 (2)	75.754 (2), 81.670 (2), 87.717 (2)
V (Å³)	3069.9 (2)	836.55 (6)	865.01 (7)	844.63 (9)
Z	8	2	2	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
μ (mm⁻¹)	0.11	0.11	0.25	0.15
Crystal size (mm)	0.30 × 0.22 × 0.18	0.30 × 0.26 × 0.25	0.28 × 0.24 × 0.22	0.21 × 0.17 × 0.05

Data collection
Diffractometer	Bruker D8 Venture dual source	Bruker D8 Venture dual source	Bruker D8 Venture dual source	Bruker D8 Venture dual source
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.890, 0.971	0.939, 0.971	0.931, 0.971	0.914, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	25982, 3518, 3130	34250, 3810, 3567	28796, 3954, 3617	38650, 3882, 3456
R_int	0.036	0.033	0.034	0.034
(sin θ/λ)_max (Å⁻¹)	0.650	0.650	0.650	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.05	0.034, 0.098, 1.05	0.029, 0.074, 1.04	0.031, 0.082, 1.04
No. of reflections	3518	3810	3954	3882
No. of parameters	220	260	243	269
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23	0.40, −0.21	0.32, −0.23	0.36, −0.22
Computer programs: APEX3 (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), XP in SHELXTL (Sheldrick, 2008 ), and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 2239906; 2239905; 2239904; 2239903

Crystal structure: contains datablocks I, II, III, IV, global. DOI: https://doi.org/10.1107/S2056989023001093/hb8053sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023001093/hb8053Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IIsup3.hkl

Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IIIsup4.hkl

Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IVsup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023001093/hb8053Isup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IIsup7.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IIIsup8.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023001093/hb8053IVsup9.cml

checkCIF report

Computing details top

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

4-(4-Nitrophenyl)piperazinium hydrogen succinate (I) top

Crystal data top

C₁₀H₁₄N₃O₂⁺·C₄H₅O₄⁻	F(000) = 1376
M_r = 325.32	D_x = 1.408 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.2747 (12) Å	Cell parameters from 9366 reflections
b = 8.0434 (4) Å	θ = 2.7–27.5°
c = 15.6617 (5) Å	µ = 0.11 mm⁻¹
β = 105.384 (2)°	T = 90 K
V = 3069.9 (2) Å³	Cut block, pale yellow
Z = 8	0.30 × 0.22 × 0.18 mm

Data collection top

Bruker D8 Venture dual source diffractometer	3518 independent reflections
Radiation source: microsource	3130 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.036
φ and ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −32→32
T_min = 0.890, T_max = 0.971	k = −10→10
25982 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0401P)² + 2.5912P] where P = (F_o² + 2F_c²)/3
3518 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

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

Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

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

	x	y	z	U_iso*/U_eq
O1	0.14051 (3)	0.80996 (12)	0.52439 (6)	0.0280 (2)
O2	0.19261 (4)	0.91415 (12)	0.64508 (5)	0.0259 (2)
N1	0.41855 (4)	1.00925 (12)	0.33747 (6)	0.01449 (19)
H1NA	0.4443 (6)	0.9234 (19)	0.3448 (9)	0.024 (4)*
H1NB	0.4279 (6)	1.087 (2)	0.3023 (10)	0.027 (4)*
N2	0.32266 (4)	1.14743 (13)	0.37425 (6)	0.0195 (2)
N3	0.18160 (4)	0.88788 (12)	0.56439 (6)	0.0193 (2)
C1	0.42042 (4)	1.07833 (14)	0.42694 (7)	0.0162 (2)
H1A	0.457208	1.125553	0.454157	0.019*
H1B	0.413555	0.988494	0.465866	0.019*
C2	0.37707 (4)	1.21296 (14)	0.41778 (7)	0.0184 (2)
H2A	0.377322	1.255726	0.477154	0.022*
H2B	0.385724	1.306506	0.382666	0.022*
C3	0.32172 (5)	1.09046 (16)	0.28539 (7)	0.0221 (3)
H3A	0.331073	1.184031	0.250990	0.027*
H3B	0.284357	1.051561	0.254685	0.027*
C4	0.36260 (4)	0.94930 (14)	0.28984 (7)	0.0185 (2)
H4A	0.352357	0.853143	0.321552	0.022*
H4B	0.362220	0.913189	0.229253	0.022*
C5	0.28969 (4)	1.07550 (14)	0.42138 (7)	0.0170 (2)
C6	0.24190 (4)	0.98517 (15)	0.37851 (7)	0.0197 (2)
H6	0.233839	0.966904	0.316459	0.024*
C7	0.20687 (4)	0.92328 (14)	0.42470 (7)	0.0187 (2)
H7	0.175211	0.862077	0.394892	0.022*
C8	0.21826 (4)	0.95117 (14)	0.51539 (7)	0.0168 (2)
C9	0.26495 (5)	1.03778 (15)	0.55941 (7)	0.0196 (2)
H9	0.272248	1.056667	0.621320	0.024*
C10	0.30066 (4)	1.09637 (15)	0.51408 (7)	0.0191 (2)
H10	0.333230	1.151757	0.545403	0.023*
O3	0.49072 (3)	0.75060 (9)	0.36438 (6)	0.01950 (18)
O4	0.56900 (3)	0.86516 (9)	0.35258 (5)	0.01772 (17)
O5	0.57855 (3)	0.25137 (9)	0.29079 (5)	0.01729 (17)
O6	0.53144 (3)	0.13451 (9)	0.37722 (5)	0.01695 (17)
H6O	0.5484 (8)	0.005 (3)	0.3625 (13)	0.065 (6)*
C11	0.53782 (4)	0.74028 (12)	0.35582 (6)	0.0127 (2)
C12	0.56315 (4)	0.57314 (12)	0.34704 (7)	0.0145 (2)
H12A	0.601509	0.572910	0.384282	0.017*
H12B	0.564189	0.558197	0.284757	0.017*
C13	0.53315 (4)	0.42686 (12)	0.37343 (7)	0.0142 (2)
H13A	0.539998	0.426052	0.438666	0.017*
H13B	0.493229	0.441729	0.347489	0.017*
C14	0.55019 (4)	0.26118 (12)	0.34399 (7)	0.0124 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0196 (4)	0.0345 (5)	0.0275 (4)	−0.0090 (4)	0.0021 (3)	0.0038 (4)
O2	0.0250 (4)	0.0339 (5)	0.0192 (4)	−0.0051 (4)	0.0063 (3)	0.0036 (3)
N1	0.0143 (4)	0.0131 (4)	0.0171 (4)	0.0014 (3)	0.0060 (3)	0.0020 (3)
N2	0.0142 (4)	0.0278 (5)	0.0177 (4)	0.0021 (4)	0.0061 (3)	−0.0008 (4)
N3	0.0158 (4)	0.0198 (5)	0.0214 (5)	0.0012 (4)	0.0031 (4)	0.0048 (4)
C1	0.0142 (5)	0.0194 (5)	0.0148 (5)	−0.0003 (4)	0.0035 (4)	0.0003 (4)
C2	0.0181 (5)	0.0182 (5)	0.0213 (5)	−0.0007 (4)	0.0091 (4)	−0.0012 (4)
C3	0.0155 (5)	0.0371 (7)	0.0141 (5)	0.0033 (5)	0.0043 (4)	0.0012 (5)
C4	0.0168 (5)	0.0231 (6)	0.0167 (5)	−0.0043 (4)	0.0064 (4)	−0.0038 (4)
C5	0.0142 (5)	0.0185 (5)	0.0192 (5)	0.0056 (4)	0.0058 (4)	0.0006 (4)
C6	0.0174 (5)	0.0240 (6)	0.0175 (5)	0.0024 (4)	0.0044 (4)	−0.0047 (4)
C7	0.0145 (5)	0.0186 (5)	0.0216 (5)	0.0014 (4)	0.0024 (4)	−0.0030 (4)
C8	0.0145 (5)	0.0165 (5)	0.0194 (5)	0.0031 (4)	0.0046 (4)	0.0031 (4)
C9	0.0186 (5)	0.0236 (6)	0.0151 (5)	−0.0009 (4)	0.0020 (4)	0.0024 (4)
C10	0.0149 (5)	0.0232 (6)	0.0176 (5)	−0.0012 (4)	0.0016 (4)	0.0007 (4)
O3	0.0158 (4)	0.0119 (4)	0.0316 (4)	0.0021 (3)	0.0078 (3)	0.0008 (3)
O4	0.0185 (4)	0.0093 (4)	0.0266 (4)	−0.0009 (3)	0.0080 (3)	−0.0010 (3)
O5	0.0229 (4)	0.0123 (4)	0.0193 (4)	−0.0004 (3)	0.0101 (3)	−0.0018 (3)
O6	0.0197 (4)	0.0089 (3)	0.0245 (4)	0.0002 (3)	0.0097 (3)	0.0013 (3)
C11	0.0155 (5)	0.0099 (5)	0.0113 (4)	0.0003 (4)	0.0010 (4)	−0.0004 (4)
C12	0.0148 (5)	0.0094 (5)	0.0192 (5)	0.0006 (4)	0.0044 (4)	−0.0010 (4)
C13	0.0163 (5)	0.0091 (5)	0.0174 (5)	0.0013 (4)	0.0048 (4)	−0.0003 (4)
C14	0.0120 (4)	0.0102 (5)	0.0131 (4)	0.0001 (4)	−0.0001 (4)	0.0000 (4)

Geometric parameters (Å, º) top

O1—N3	1.2323 (13)	C6—C7	1.3763 (16)
O2—N3	1.2380 (13)	C6—H6	0.9500
N1—C4	1.4930 (13)	C7—C8	1.3906 (15)
N1—C1	1.4964 (14)	C7—H7	0.9500
N1—H1NA	0.934 (15)	C8—C9	1.3861 (16)
N1—H1NB	0.903 (16)	C9—C10	1.3714 (16)
N2—C5	1.3784 (14)	C9—H9	0.9500
N2—C3	1.4594 (14)	C10—H10	0.9500
N2—C2	1.4618 (14)	O3—C11	1.2356 (13)
N3—C8	1.4437 (14)	O4—C11	1.2860 (13)
C1—C2	1.5199 (15)	O5—C14	1.2374 (13)
C1—H1A	0.9900	O6—H6O	1.17 (2)
C1—H1B	0.9900	O6—C14	1.2901 (13)
C2—H2A	0.9900	O6—H6O	1.17 (2)
C2—H2B	0.9900	C11—C12	1.5109 (14)
C3—C4	1.5241 (16)	C12—C13	1.5154 (14)
C3—H3A	0.9900	C12—H12A	0.9900
C3—H3B	0.9900	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.5097 (14)
C4—H4B	0.9900	C13—H13A	0.9900
C5—C10	1.4139 (15)	C13—H13B	0.9900
C5—C6	1.4170 (16)

C4—N1—C1	112.23 (8)	C10—C5—C6	117.24 (10)
C4—N1—H1NA	111.0 (9)	C7—C6—C5	121.52 (10)
C1—N1—H1NA	108.1 (9)	C7—C6—H6	119.2
C4—N1—H1NB	106.6 (9)	C5—C6—H6	119.2
C1—N1—H1NB	111.6 (10)	C6—C7—C8	119.39 (10)
H1NA—N1—H1NB	107.3 (12)	C6—C7—H7	120.3
C5—N2—C3	121.32 (10)	C8—C7—H7	120.3
C5—N2—C2	121.95 (9)	C9—C8—C7	120.48 (10)
C3—N2—C2	109.46 (8)	C9—C8—N3	119.65 (10)
O1—N3—O2	122.46 (10)	C7—C8—N3	119.87 (10)
O1—N3—C8	118.84 (9)	C10—C9—C8	120.37 (10)
O2—N3—C8	118.70 (9)	C10—C9—H9	119.8
N1—C1—C2	109.46 (8)	C8—C9—H9	119.8
N1—C1—H1A	109.8	C9—C10—C5	120.93 (10)
C2—C1—H1A	109.8	C9—C10—H10	119.5
N1—C1—H1B	109.8	C5—C10—H10	119.5
C2—C1—H1B	109.8	H6O—O6—C14	115.4 (10)
H1A—C1—H1B	108.2	H6O—O6—H6O	0 (3)
N2—C2—C1	110.65 (9)	C14—O6—H6O	115.4 (10)
N2—C2—H2A	109.5	O3—C11—O4	124.74 (9)
C1—C2—H2A	109.5	O3—C11—C12	120.89 (9)
N2—C2—H2B	109.5	O4—C11—C12	114.37 (9)
C1—C2—H2B	109.5	C11—C12—C13	114.29 (8)
H2A—C2—H2B	108.1	C11—C12—H12A	108.7
N2—C3—C4	110.55 (9)	C13—C12—H12A	108.7
N2—C3—H3A	109.5	C11—C12—H12B	108.7
C4—C3—H3A	109.5	C13—C12—H12B	108.7
N2—C3—H3B	109.5	H12A—C12—H12B	107.6
C4—C3—H3B	109.5	C14—C13—C12	113.47 (8)
H3A—C3—H3B	108.1	C14—C13—H13A	108.9
N1—C4—C3	108.84 (9)	C12—C13—H13A	108.9
N1—C4—H4A	109.9	C14—C13—H13B	108.9
C3—C4—H4A	109.9	C12—C13—H13B	108.9
N1—C4—H4B	109.9	H13A—C13—H13B	107.7
C3—C4—H4B	109.9	O5—C14—O6	124.17 (9)
H4A—C4—H4B	108.3	O5—C14—C13	121.67 (9)
N2—C5—C10	121.22 (10)	O6—C14—C13	114.14 (9)
N2—C5—C6	121.46 (10)

C4—N1—C1—C2	−54.52 (12)	O1—N3—C8—C9	−179.41 (10)
C5—N2—C2—C1	89.04 (12)	O2—N3—C8—C9	0.67 (16)
C3—N2—C2—C1	−61.41 (12)	O1—N3—C8—C7	−0.13 (15)
N1—C1—C2—N2	57.02 (11)	O2—N3—C8—C7	179.94 (10)
C5—N2—C3—C4	−88.50 (12)	C7—C8—C9—C10	−0.33 (17)
C2—N2—C3—C4	62.17 (12)	N3—C8—C9—C10	178.94 (10)
C1—N1—C4—C3	54.94 (11)	C8—C9—C10—C5	2.44 (18)
N2—C3—C4—N1	−58.37 (12)	N2—C5—C10—C9	173.84 (11)
C3—N2—C5—C10	162.34 (10)	C6—C5—C10—C9	−2.92 (17)
C2—N2—C5—C10	15.32 (16)	O3—C11—C12—C13	−15.24 (14)
C3—N2—C5—C6	−21.04 (16)	O4—C11—C12—C13	165.46 (9)
C2—N2—C5—C6	−168.06 (10)	C11—C12—C13—C14	166.06 (8)
N2—C5—C6—C7	−175.36 (10)	H6O—O6—C14—O5	9.0 (11)
C10—C5—C6—C7	1.39 (16)	H6O—O6—C14—C13	−172.7 (11)
C5—C6—C7—C8	0.62 (17)	C12—C13—C14—O5	−11.74 (14)
C6—C7—C8—C9	−1.19 (17)	C12—C13—C14—O6	169.97 (9)
C6—C7—C8—N3	179.54 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3	0.934 (15)	1.793 (16)	2.7250 (12)	175.5 (13)
N1—H1NB···O5ⁱ	0.903 (16)	1.945 (16)	2.8127 (12)	160.5 (13)
O6—H6O···O4ⁱⁱ	1.17 (2)	1.27 (2)	2.4367 (10)	176 (2)
C1—H1A···O6ⁱⁱⁱ	0.99	2.49	3.1374 (13)	123
C3—H3A···O5ⁱ	0.99	2.59	3.3238 (15)	130
C3—H3B···O2^iv	0.99	2.51	3.4168 (15)	153
C4—H4A···O2^v	0.99	2.55	3.5053 (15)	162
C4—H4B···O4^vi	0.99	2.45	3.2354 (13)	136
C10—H10···O4^vii	0.95	2.57	3.4146 (13)	149

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

4-(4-Nitrophenyl)piperazinium 4-aminobenzoate monohydrate (II) top

Crystal data top

C₁₀H₁₄N₃O₂⁺·C₇H₆NO₂⁻·H₂O	Z = 2
M_r = 362.38	F(000) = 384
Triclinic, P1	D_x = 1.439 Mg m⁻³
a = 6.0453 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3930 (3) Å	Cell parameters from 9362 reflections
c = 19.1439 (6) Å	θ = 2.8–27.5°
α = 79.482 (2)°	µ = 0.11 mm⁻¹
β = 89.215 (1)°	T = 90 K
γ = 83.967 (1)°	Cut block, pale yellow
V = 836.55 (6) Å³	0.30 × 0.26 × 0.25 mm

Data collection top

Bruker D8 Venture dual source diffractometer	3810 independent reflections
Radiation source: microsource	3567 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.033
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→7
T_min = 0.939, T_max = 0.971	k = −9→9
34250 measured reflections	l = −23→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0553P)² + 0.2799P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3810 reflections	Δρ_max = 0.40 e Å⁻³
260 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (12)

Special details top

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

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

	x	y	z	U_iso*/U_eq
O1	0.53605 (15)	0.20260 (13)	1.00635 (4)	0.0313 (2)
O2	0.23072 (15)	0.38290 (13)	0.99145 (5)	0.0317 (2)
N1	0.76952 (13)	0.71108 (11)	0.54685 (4)	0.01334 (18)
H1NA	0.813 (3)	0.774 (2)	0.5028 (9)	0.034 (4)*
H1NB	0.732 (2)	0.596 (2)	0.5393 (7)	0.023 (3)*
N2	0.68305 (13)	0.65351 (11)	0.69771 (4)	0.01221 (18)
N3	0.41469 (16)	0.32803 (12)	0.97077 (5)	0.0193 (2)
C1	0.57897 (16)	0.81697 (13)	0.57606 (5)	0.0146 (2)
H1C	0.454845	0.844383	0.541278	0.018*
H1D	0.624218	0.935914	0.584689	0.018*
C2	0.50264 (15)	0.70618 (13)	0.64495 (5)	0.0137 (2)
H2A	0.379688	0.780329	0.664798	0.016*
H2B	0.444540	0.592986	0.635118	0.016*
C3	0.88481 (15)	0.56519 (13)	0.66941 (5)	0.0143 (2)
H3A	0.857762	0.439718	0.662658	0.017*
H3B	1.007080	0.551797	0.704450	0.017*
C4	0.95609 (16)	0.67460 (13)	0.59914 (5)	0.0149 (2)
H4A	1.003928	0.793496	0.606856	0.018*
H4B	1.084141	0.604189	0.580091	0.018*
C5	0.61991 (16)	0.57294 (13)	0.76590 (5)	0.01256 (19)
C6	0.76269 (16)	0.43863 (14)	0.81014 (5)	0.0167 (2)
H6	0.905917	0.401074	0.793498	0.020*
C7	0.69753 (17)	0.36046 (14)	0.87753 (5)	0.0182 (2)
H7	0.795230	0.270086	0.907019	0.022*
C8	0.48877 (17)	0.41525 (13)	0.90149 (5)	0.0158 (2)
C9	0.34481 (17)	0.54901 (14)	0.86003 (5)	0.0170 (2)
H9	0.202792	0.586433	0.877573	0.020*
C10	0.41010 (16)	0.62734 (13)	0.79291 (5)	0.0159 (2)
H10	0.311958	0.719530	0.764402	0.019*
O3	0.91205 (12)	0.87584 (10)	0.41666 (4)	0.01794 (17)
O4	0.63869 (13)	0.73092 (11)	0.38233 (4)	0.02436 (19)
N4	0.99454 (17)	1.07521 (13)	0.07778 (5)	0.0216 (2)
H4NA	0.881 (3)	1.094 (2)	0.0482 (9)	0.039 (4)*
H4NB	1.098 (3)	1.152 (2)	0.0683 (9)	0.036 (4)*
C11	0.79522 (16)	0.82924 (13)	0.36896 (5)	0.0147 (2)
C12	0.84904 (15)	0.89608 (12)	0.29267 (5)	0.0132 (2)
C13	1.04220 (16)	0.98073 (13)	0.27286 (5)	0.0139 (2)
H13	1.142098	0.996856	0.308568	0.017*
C14	1.09049 (16)	1.04151 (13)	0.20203 (5)	0.0155 (2)
H14	1.223476	1.097509	0.189691	0.019*
C15	0.94427 (17)	1.02089 (13)	0.14843 (5)	0.0155 (2)
C16	0.74953 (17)	0.93703 (14)	0.16826 (5)	0.0171 (2)
H16	0.647635	0.923274	0.132721	0.020*
C17	0.70465 (16)	0.87434 (13)	0.23895 (5)	0.0154 (2)
H17	0.573636	0.815474	0.251325	0.019*
O1W	0.29390 (13)	0.65167 (10)	0.46397 (4)	0.01758 (17)
H1W1	0.183 (3)	0.730 (2)	0.4450 (9)	0.037 (4)*
H2W1	0.410 (3)	0.681 (2)	0.4372 (9)	0.041 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0317 (5)	0.0350 (5)	0.0201 (4)	0.0004 (4)	0.0010 (3)	0.0114 (3)
O2	0.0324 (5)	0.0330 (5)	0.0247 (4)	0.0021 (4)	0.0150 (3)	0.0036 (3)
N1	0.0154 (4)	0.0138 (4)	0.0104 (4)	−0.0018 (3)	0.0009 (3)	−0.0012 (3)
N2	0.0114 (4)	0.0134 (4)	0.0108 (4)	−0.0001 (3)	0.0004 (3)	−0.0004 (3)
N3	0.0251 (5)	0.0189 (4)	0.0139 (4)	−0.0055 (3)	0.0030 (3)	−0.0014 (3)
C1	0.0158 (4)	0.0143 (4)	0.0125 (4)	0.0010 (3)	0.0001 (3)	−0.0009 (3)
C2	0.0121 (4)	0.0163 (4)	0.0117 (4)	0.0005 (3)	−0.0001 (3)	−0.0008 (3)
C3	0.0124 (4)	0.0168 (4)	0.0122 (4)	0.0009 (3)	0.0014 (3)	−0.0001 (3)
C4	0.0130 (4)	0.0182 (5)	0.0128 (4)	−0.0020 (3)	0.0010 (3)	−0.0009 (3)
C5	0.0148 (4)	0.0114 (4)	0.0118 (4)	−0.0027 (3)	0.0005 (3)	−0.0021 (3)
C6	0.0148 (4)	0.0189 (5)	0.0147 (4)	0.0007 (4)	0.0013 (3)	−0.0001 (4)
C7	0.0195 (5)	0.0190 (5)	0.0141 (4)	0.0002 (4)	−0.0010 (4)	0.0013 (4)
C8	0.0214 (5)	0.0152 (4)	0.0110 (4)	−0.0049 (4)	0.0026 (4)	−0.0014 (3)
C9	0.0176 (5)	0.0160 (5)	0.0169 (5)	−0.0009 (4)	0.0046 (4)	−0.0029 (4)
C10	0.0168 (5)	0.0142 (4)	0.0151 (4)	0.0015 (3)	0.0017 (4)	−0.0003 (3)
O3	0.0217 (4)	0.0183 (4)	0.0128 (3)	−0.0012 (3)	0.0020 (3)	−0.0006 (3)
O4	0.0247 (4)	0.0269 (4)	0.0211 (4)	−0.0106 (3)	0.0074 (3)	0.0006 (3)
N4	0.0260 (5)	0.0244 (5)	0.0130 (4)	−0.0024 (4)	0.0022 (4)	0.0000 (3)
C11	0.0151 (4)	0.0116 (4)	0.0155 (4)	0.0021 (3)	0.0036 (3)	0.0001 (3)
C12	0.0145 (4)	0.0107 (4)	0.0131 (4)	0.0007 (3)	0.0023 (3)	−0.0005 (3)
C13	0.0145 (4)	0.0131 (4)	0.0141 (4)	−0.0010 (3)	0.0005 (3)	−0.0027 (3)
C14	0.0151 (4)	0.0147 (4)	0.0163 (5)	−0.0030 (3)	0.0036 (3)	−0.0017 (3)
C15	0.0196 (5)	0.0125 (4)	0.0134 (4)	0.0013 (3)	0.0025 (3)	−0.0013 (3)
C16	0.0190 (5)	0.0158 (4)	0.0163 (5)	−0.0012 (4)	−0.0031 (4)	−0.0027 (4)
C17	0.0136 (4)	0.0130 (4)	0.0191 (5)	−0.0019 (3)	0.0007 (3)	−0.0012 (3)
O1W	0.0171 (4)	0.0180 (4)	0.0176 (4)	−0.0034 (3)	0.0037 (3)	−0.0023 (3)

Geometric parameters (Å, º) top

O1—N3	1.2256 (12)	C7—C8	1.3827 (14)
O2—N3	1.2288 (12)	C7—H7	0.9500
N1—C1	1.4850 (12)	C8—C9	1.3845 (14)
N1—C4	1.4884 (12)	C9—C10	1.3801 (13)
N1—H1NA	0.936 (17)	C9—H9	0.9500
N1—H1NB	0.942 (15)	C10—H10	0.9500
N2—C5	1.3980 (12)	O3—C11	1.2787 (13)
N2—C3	1.4668 (12)	O4—C11	1.2488 (13)
N2—C2	1.4694 (12)	N4—C15	1.3781 (13)
N3—C8	1.4517 (12)	N4—H4NA	0.879 (18)
C1—C2	1.5137 (12)	N4—H4NB	0.886 (18)
C1—H1C	0.9900	C11—C12	1.4968 (12)
C1—H1D	0.9900	C12—C13	1.3978 (13)
C2—H2A	0.9900	C12—C17	1.3999 (13)
C2—H2B	0.9900	C13—C14	1.3856 (13)
C3—C4	1.5197 (12)	C13—H13	0.9500
C3—H3A	0.9900	C14—C15	1.4028 (14)
C3—H3B	0.9900	C14—H14	0.9500
C4—H4A	0.9900	C15—C16	1.4034 (14)
C4—H4B	0.9900	C16—C17	1.3810 (14)
C5—C6	1.4076 (13)	C16—H16	0.9500
C5—C10	1.4102 (13)	C17—H17	0.9500
C6—C7	1.3838 (13)	O1W—H1W1	0.877 (18)
C6—H6	0.9500	O1W—H2W1	0.885 (18)

C1—N1—C4	108.92 (7)	C7—C6—H6	119.5
C1—N1—H1NA	111.3 (10)	C5—C6—H6	119.5
C4—N1—H1NA	111.3 (10)	C8—C7—C6	119.32 (9)
C1—N1—H1NB	111.3 (9)	C8—C7—H7	120.3
C4—N1—H1NB	107.5 (8)	C6—C7—H7	120.3
H1NA—N1—H1NB	106.4 (13)	C7—C8—C9	121.45 (9)
C5—N2—C3	116.22 (7)	C7—C8—N3	119.79 (9)
C5—N2—C2	115.77 (7)	C9—C8—N3	118.74 (9)
C3—N2—C2	112.92 (7)	C10—C9—C8	119.20 (9)
O1—N3—O2	122.35 (9)	C10—C9—H9	120.4
O1—N3—C8	119.31 (9)	C8—C9—H9	120.4
O2—N3—C8	118.34 (9)	C9—C10—C5	121.17 (9)
N1—C1—C2	110.02 (7)	C9—C10—H10	119.4
N1—C1—H1C	109.7	C5—C10—H10	119.4
C2—C1—H1C	109.7	C15—N4—H4NA	115.6 (11)
N1—C1—H1D	109.7	C15—N4—H4NB	116.4 (11)
C2—C1—H1D	109.7	H4NA—N4—H4NB	116.6 (15)
H1C—C1—H1D	108.2	O4—C11—O3	123.77 (9)
N2—C2—C1	112.23 (8)	O4—C11—C12	118.01 (9)
N2—C2—H2A	109.2	O3—C11—C12	118.21 (9)
C1—C2—H2A	109.2	C13—C12—C17	118.22 (9)
N2—C2—H2B	109.2	C13—C12—C11	121.69 (9)
C1—C2—H2B	109.2	C17—C12—C11	120.10 (9)
H2A—C2—H2B	107.9	C14—C13—C12	121.14 (9)
N2—C3—C4	112.56 (8)	C14—C13—H13	119.4
N2—C3—H3A	109.1	C12—C13—H13	119.4
C4—C3—H3A	109.1	C13—C14—C15	120.42 (9)
N2—C3—H3B	109.1	C13—C14—H14	119.8
C4—C3—H3B	109.1	C15—C14—H14	119.8
H3A—C3—H3B	107.8	N4—C15—C14	120.82 (9)
N1—C4—C3	110.60 (8)	N4—C15—C16	120.62 (9)
N1—C4—H4A	109.5	C14—C15—C16	118.51 (9)
C3—C4—H4A	109.5	C17—C16—C15	120.61 (9)
N1—C4—H4B	109.5	C17—C16—H16	119.7
C3—C4—H4B	109.5	C15—C16—H16	119.7
H4A—C4—H4B	108.1	C16—C17—C12	121.09 (9)
N2—C5—C6	121.76 (9)	C16—C17—H17	119.5
N2—C5—C10	120.38 (8)	C12—C17—H17	119.5
C6—C5—C10	117.85 (9)	H1W1—O1W—H2W1	104.7 (15)
C7—C6—C5	120.98 (9)

C4—N1—C1—C2	−60.5 (1)	O2—N3—C8—C9	−3.55 (14)
C5—N2—C2—C1	171.62 (8)	C7—C8—C9—C10	0.95 (16)
C3—N2—C2—C1	−50.91 (10)	N3—C8—C9—C10	−177.35 (9)
N1—C1—C2—N2	56.6 (1)	C8—C9—C10—C5	0.26 (15)
C5—N2—C3—C4	−173.16 (8)	N2—C5—C10—C9	179.86 (9)
C2—N2—C3—C4	49.57 (11)	C6—C5—C10—C9	−1.23 (15)
C1—N1—C4—C3	59.29 (10)	O4—C11—C12—C13	−169.47 (9)
N2—C3—C4—N1	−54.06 (10)	O3—C11—C12—C13	10.47 (13)
C3—N2—C5—C6	11.92 (13)	O4—C11—C12—C17	10.42 (14)
C2—N2—C5—C6	147.97 (9)	O3—C11—C12—C17	−169.64 (9)
C3—N2—C5—C10	−169.20 (8)	C17—C12—C13—C14	−0.09 (14)
C2—N2—C5—C10	−33.16 (12)	C11—C12—C13—C14	179.80 (8)
N2—C5—C6—C7	179.93 (9)	C12—C13—C14—C15	0.67 (14)
C10—C5—C6—C7	1.03 (15)	C13—C14—C15—N4	−177.78 (9)
C5—C6—C7—C8	0.12 (16)	C13—C14—C15—C16	−0.24 (14)
C6—C7—C8—C9	−1.14 (16)	N4—C15—C16—C17	176.78 (9)
C6—C7—C8—N3	177.14 (9)	C14—C15—C16—C17	−0.77 (14)
O1—N3—C8—C7	−2.18 (15)	C15—C16—C17—C12	1.38 (15)
O2—N3—C8—C7	178.12 (10)	C13—C12—C17—C16	−0.93 (14)
O1—N3—C8—C9	176.15 (10)	C11—C12—C17—C16	179.18 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3	0.936 (17)	1.804 (17)	2.737 (1)	174.7 (15)
N1—H1NB···O1Wⁱ	0.942 (15)	1.864 (15)	2.7934 (11)	168.4 (13)
N4—H4NA···O1ⁱⁱ	0.879 (18)	2.258 (18)	3.0861 (13)	156.9 (15)
N4—H4NB···O2ⁱⁱⁱ	0.886 (18)	2.248 (17)	3.0315 (13)	147.3 (14)
O1W—H1W1···O3^iv	0.877 (18)	1.890 (18)	2.7569 (11)	169.7 (16)
O1W—H2W1···O4	0.885 (18)	1.755 (18)	2.6388 (11)	177.2 (17)
C1—H1C···O1W	0.99	2.50	3.2511 (12)	132
C2—H2B···O4ⁱ	0.99	2.58	3.5572 (13)	170
C4—H4A···O3^v	0.99	2.51	3.4578 (12)	161
C4—H4B···O1W^vi	0.99	2.53	3.2921 (12)	134

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

4-(4-Nitrophenyl)piperazinium 2-(4-chlorophenyl)acetate (III) top

Crystal data top

C₁₀H₁₄N₃O₂⁺·C₈H₆ClO₂⁻	Z = 2
M_r = 377.82	F(000) = 396
Triclinic, P1	D_x = 1.451 Mg m⁻³
a = 6.8051 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3927 (5) Å	Cell parameters from 9810 reflections
c = 14.3869 (7) Å	θ = 2.6–27.5°
α = 83.849 (2)°	µ = 0.25 mm⁻¹
β = 81.283 (2)°	T = 90 K
γ = 72.492 (2)°	Rounded block, pale yellow
V = 865.01 (7) Å³	0.28 × 0.24 × 0.22 mm

Data collection top

Bruker D8 Venture dual source diffractometer	3954 independent reflections
Radiation source: microsource	3617 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.034
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→8
T_min = 0.931, T_max = 0.971	k = −12→12
28796 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: mixed
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0293P)² + 0.3972P] where P = (F_o² + 2F_c²)/3
3954 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

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

	x	y	z	U_iso*/U_eq
O1	−0.50792 (15)	0.72253 (11)	−0.02713 (7)	0.0316 (2)
O2	−0.25948 (17)	0.82570 (11)	−0.05317 (7)	0.0356 (2)
N1	0.26456 (14)	0.13828 (11)	0.41177 (7)	0.01585 (19)
H1NA	0.325 (2)	0.0464 (18)	0.4359 (10)	0.026 (4)*
H1NB	0.269 (2)	0.2061 (18)	0.4542 (11)	0.032 (4)*
N2	0.07010 (14)	0.32686 (10)	0.26302 (6)	0.01586 (19)
N3	−0.34059 (17)	0.73363 (11)	−0.01097 (7)	0.0227 (2)
C1	0.38614 (17)	0.16486 (12)	0.32016 (8)	0.0176 (2)
H1A	0.395730	0.086035	0.277758	0.021*
H1B	0.528798	0.159661	0.330426	0.021*
C2	0.28355 (16)	0.31715 (12)	0.27444 (8)	0.0172 (2)
H2A	0.283868	0.396692	0.314290	0.021*
H2B	0.362111	0.331786	0.212161	0.021*
C3	−0.05253 (16)	0.30313 (12)	0.35323 (7)	0.0156 (2)
H3A	−0.195330	0.309614	0.342459	0.019*
H3B	−0.061304	0.382276	0.395239	0.019*
C4	0.04638 (16)	0.15129 (12)	0.39986 (8)	0.0156 (2)
H4A	−0.033315	0.138579	0.462142	0.019*
H4B	0.044013	0.071645	0.360567	0.019*
C5	−0.02922 (16)	0.43171 (12)	0.19619 (7)	0.0151 (2)
C6	−0.21686 (17)	0.42157 (12)	0.17151 (8)	0.0176 (2)
H6	−0.273862	0.345143	0.201503	0.021*
C7	−0.31899 (17)	0.52046 (12)	0.10471 (8)	0.0183 (2)
H7	−0.446340	0.513477	0.089059	0.022*
C8	−0.23292 (18)	0.63078 (12)	0.06044 (7)	0.0177 (2)
C9	−0.04689 (18)	0.64229 (12)	0.08123 (8)	0.0185 (2)
H9	0.011220	0.716896	0.049151	0.022*
C10	0.05405 (17)	0.54344 (12)	0.14959 (8)	0.0168 (2)
H10	0.181000	0.551621	0.164951	0.020*
Cl1	1.20054 (4)	−0.01622 (3)	0.85294 (2)	0.02223 (8)
O3	0.31330 (12)	0.34221 (9)	0.51721 (6)	0.01836 (17)
O4	0.60380 (12)	0.15406 (8)	0.52384 (6)	0.01855 (17)
C11	0.48457 (16)	0.27847 (11)	0.54780 (7)	0.0141 (2)
C12	0.54892 (18)	0.36457 (12)	0.61677 (8)	0.0187 (2)
H12A	0.600482	0.444591	0.580440	0.022*
H12B	0.424032	0.413504	0.659594	0.022*
C13	0.71304 (17)	0.27174 (12)	0.67559 (8)	0.0160 (2)
C14	0.65746 (17)	0.19582 (12)	0.75951 (8)	0.0176 (2)
H14	0.514929	0.204580	0.779430	0.021*
C15	0.80586 (18)	0.10768 (12)	0.81460 (8)	0.0179 (2)
H15	0.765725	0.057433	0.871881	0.022*
C16	1.01349 (17)	0.09451 (12)	0.78437 (8)	0.0166 (2)
C17	1.07373 (17)	0.16949 (12)	0.70198 (8)	0.0176 (2)
H17	1.216498	0.160159	0.682282	0.021*
C18	0.92272 (17)	0.25871 (12)	0.64834 (8)	0.0171 (2)
H18	0.963297	0.311542	0.592260	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0330 (5)	0.0302 (5)	0.0312 (5)	−0.0051 (4)	−0.0172 (4)	0.0068 (4)
O2	0.0498 (6)	0.0257 (5)	0.0320 (5)	−0.0142 (4)	−0.0119 (4)	0.0144 (4)
N1	0.0159 (4)	0.0129 (4)	0.0185 (5)	−0.0027 (4)	−0.0054 (4)	0.0004 (4)
N2	0.0133 (4)	0.0189 (5)	0.0153 (4)	−0.0052 (3)	−0.0029 (3)	0.0026 (3)
N3	0.0318 (6)	0.0165 (5)	0.0170 (5)	−0.0019 (4)	−0.0061 (4)	0.0004 (4)
C1	0.0143 (5)	0.0182 (5)	0.0198 (5)	−0.0033 (4)	−0.0026 (4)	−0.0023 (4)
C2	0.0144 (5)	0.0203 (5)	0.0178 (5)	−0.0062 (4)	−0.0037 (4)	0.0007 (4)
C3	0.0148 (5)	0.0160 (5)	0.0147 (5)	−0.0033 (4)	−0.0019 (4)	0.0012 (4)
C4	0.0162 (5)	0.0141 (5)	0.0175 (5)	−0.0053 (4)	−0.0043 (4)	0.0004 (4)
C5	0.0168 (5)	0.0150 (5)	0.0127 (5)	−0.0033 (4)	−0.0017 (4)	−0.0017 (4)
C6	0.0188 (5)	0.0176 (5)	0.0173 (5)	−0.0073 (4)	−0.0033 (4)	0.0019 (4)
C7	0.0177 (5)	0.0195 (5)	0.0174 (5)	−0.0043 (4)	−0.0041 (4)	−0.0007 (4)
C8	0.0242 (6)	0.0138 (5)	0.0124 (5)	−0.0012 (4)	−0.0031 (4)	−0.0005 (4)
C9	0.0267 (6)	0.0138 (5)	0.0153 (5)	−0.0073 (4)	−0.0002 (4)	−0.0017 (4)
C10	0.0195 (5)	0.0168 (5)	0.0158 (5)	−0.0072 (4)	−0.0021 (4)	−0.0027 (4)
Cl1	0.02364 (15)	0.02014 (14)	0.02045 (14)	−0.00019 (11)	−0.00884 (10)	0.00015 (10)
O3	0.0165 (4)	0.0167 (4)	0.0219 (4)	−0.0031 (3)	−0.0066 (3)	−0.0009 (3)
O4	0.0207 (4)	0.0131 (4)	0.0216 (4)	−0.0023 (3)	−0.0063 (3)	−0.0023 (3)
C11	0.0171 (5)	0.0121 (5)	0.0138 (5)	−0.0064 (4)	−0.0022 (4)	0.0024 (4)
C12	0.0220 (5)	0.0131 (5)	0.0216 (6)	−0.0029 (4)	−0.0082 (4)	−0.0023 (4)
C13	0.0202 (5)	0.0116 (5)	0.0173 (5)	−0.0042 (4)	−0.0055 (4)	−0.0035 (4)
C14	0.0174 (5)	0.0155 (5)	0.0209 (5)	−0.0053 (4)	−0.0024 (4)	−0.0036 (4)
C15	0.0232 (5)	0.0144 (5)	0.0167 (5)	−0.0064 (4)	−0.0025 (4)	−0.0005 (4)
C16	0.0199 (5)	0.0127 (5)	0.0170 (5)	−0.0019 (4)	−0.0066 (4)	−0.0024 (4)
C17	0.0175 (5)	0.0186 (5)	0.0181 (5)	−0.0061 (4)	−0.0026 (4)	−0.0038 (4)
C18	0.0226 (5)	0.0156 (5)	0.0149 (5)	−0.0076 (4)	−0.0032 (4)	−0.0014 (4)

Geometric parameters (Å, º) top

O1—N3	1.2322 (14)	C7—C8	1.3904 (16)
O2—N3	1.2224 (14)	C7—H7	0.9500
N1—C1	1.4857 (14)	C8—C9	1.3812 (16)
N1—C4	1.4873 (13)	C9—C10	1.3880 (16)
N1—H1NA	0.894 (16)	C9—H9	0.9500
N1—H1NB	0.937 (16)	C10—H10	0.9500
N2—C5	1.3945 (14)	Cl1—C16	1.7434 (11)
N2—C2	1.4610 (13)	O3—C11	1.2609 (13)
N2—C3	1.4670 (13)	O4—C11	1.2545 (13)
N3—C8	1.4544 (14)	C11—C12	1.5319 (15)
C1—C2	1.5175 (15)	C12—C13	1.5055 (15)
C1—H1A	0.9900	C12—H12A	0.9900
C1—H1B	0.9900	C12—H12B	0.9900
C2—H2A	0.9900	C13—C18	1.3930 (16)
C2—H2B	0.9900	C13—C14	1.3959 (16)
C3—C4	1.5137 (14)	C14—C15	1.3901 (15)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—C16	1.3860 (16)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—C17	1.3844 (16)
C5—C10	1.4014 (15)	C17—C18	1.3920 (15)
C5—C6	1.4084 (15)	C17—H17	0.9500
C6—C7	1.3755 (15)	C18—H18	0.9500
C6—H6	0.9500

C1—N1—C4	111.22 (8)	C5—C6—H6	119.4
C1—N1—H1NA	108.7 (10)	C6—C7—C8	118.96 (10)
C4—N1—H1NA	109.3 (10)	C6—C7—H7	120.5
C1—N1—H1NB	109.4 (10)	C8—C7—H7	120.5
C4—N1—H1NB	110.8 (10)	C9—C8—C7	121.62 (10)
H1NA—N1—H1NB	107.3 (13)	C9—C8—N3	119.78 (10)
C5—N2—C2	118.82 (9)	C7—C8—N3	118.58 (10)
C5—N2—C3	117.88 (9)	C8—C9—C10	119.14 (10)
C2—N2—C3	112.05 (8)	C8—C9—H9	120.4
O2—N3—O1	123.01 (10)	C10—C9—H9	120.4
O2—N3—C8	118.49 (10)	C9—C10—C5	120.73 (10)
O1—N3—C8	118.5 (1)	C9—C10—H10	119.6
N1—C1—C2	110.44 (9)	C5—C10—H10	119.6
N1—C1—H1A	109.6	O4—C11—O3	124.59 (10)
C2—C1—H1A	109.6	O4—C11—C12	119.40 (9)
N1—C1—H1B	109.6	O3—C11—C12	115.99 (9)
C2—C1—H1B	109.6	C13—C12—C11	115.29 (9)
H1A—C1—H1B	108.1	C13—C12—H12A	108.5
N2—C2—C1	109.47 (9)	C11—C12—H12A	108.5
N2—C2—H2A	109.8	C13—C12—H12B	108.5
C1—C2—H2A	109.8	C11—C12—H12B	108.5
N2—C2—H2B	109.8	H12A—C12—H12B	107.5
C1—C2—H2B	109.8	C18—C13—C14	118.25 (10)
H2A—C2—H2B	108.2	C18—C13—C12	121.49 (10)
N2—C3—C4	110.37 (9)	C14—C13—C12	120.26 (10)
N2—C3—H3A	109.6	C15—C14—C13	121.52 (10)
C4—C3—H3A	109.6	C15—C14—H14	119.2
N2—C3—H3B	109.6	C13—C14—H14	119.2
C4—C3—H3B	109.6	C16—C15—C14	118.74 (10)
H3A—C3—H3B	108.1	C16—C15—H15	120.6
N1—C4—C3	109.74 (9)	C14—C15—H15	120.6
N1—C4—H4A	109.7	C17—C16—C15	121.2 (1)
C3—C4—H4A	109.7	C17—C16—Cl1	119.80 (9)
N1—C4—H4B	109.7	C15—C16—Cl1	119.00 (9)
C3—C4—H4B	109.7	C16—C17—C18	119.24 (10)
H4A—C4—H4B	108.2	C16—C17—H17	120.4
N2—C5—C10	122.74 (10)	C18—C17—H17	120.4
N2—C5—C6	118.81 (10)	C17—C18—C13	121.03 (10)
C10—C5—C6	118.39 (10)	C17—C18—H18	119.5
C7—C6—C5	121.12 (10)	C13—C18—H18	119.5
C7—C6—H6	119.4

C4—N1—C1—C2	56.92 (11)	O1—N3—C8—C7	2.59 (15)
C5—N2—C2—C1	−158.61 (9)	C7—C8—C9—C10	−1.54 (17)
C3—N2—C2—C1	58.37 (11)	N3—C8—C9—C10	179.95 (10)
N1—C1—C2—N2	−56.83 (11)	C8—C9—C10—C5	0.95 (16)
C5—N2—C3—C4	157.89 (9)	N2—C5—C10—C9	177.79 (10)
C2—N2—C3—C4	−58.71 (11)	C6—C5—C10—C9	0.44 (16)
C1—N1—C4—C3	−56.34 (11)	O4—C11—C12—C13	−20.24 (15)
N2—C3—C4—N1	56.40 (11)	O3—C11—C12—C13	161.46 (10)
C2—N2—C5—C10	−10.02 (15)	C11—C12—C13—C18	94.64 (12)
C3—N2—C5—C10	130.87 (11)	C11—C12—C13—C14	−85.23 (13)
C2—N2—C5—C6	167.32 (10)	C18—C13—C14—C15	−0.76 (16)
C3—N2—C5—C6	−51.78 (14)	C12—C13—C14—C15	179.12 (10)
N2—C5—C6—C7	−178.76 (10)	C13—C14—C15—C16	−0.64 (16)
C10—C5—C6—C7	−1.30 (16)	C14—C15—C16—C17	1.28 (16)
C5—C6—C7—C8	0.76 (17)	C14—C15—C16—Cl1	−179.84 (8)
C6—C7—C8—C9	0.69 (17)	C15—C16—C17—C18	−0.50 (16)
C6—C7—C8—N3	179.21 (10)	Cl1—C16—C17—C18	−179.38 (8)
O2—N3—C8—C9	2.19 (16)	C16—C17—C18—C13	−0.95 (16)
O1—N3—C8—C9	−178.86 (10)	C14—C13—C18—C17	1.56 (15)
O2—N3—C8—C7	−176.36 (11)	C12—C13—C18—C17	−178.32 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O4ⁱ	0.894 (16)	1.848 (16)	2.7252 (12)	166.3 (14)
N1—H1NB···O3	0.937 (16)	1.765 (17)	2.6903 (12)	169.0 (15)
C4—H4A···O4ⁱⁱ	0.99	2.46	3.2539 (14)	137
C7—H7···O1ⁱⁱⁱ	0.95	2.59	3.2256 (15)	124
C12—H12A···O3^iv	0.99	2.49	3.4710 (14)	173
C15—H15···O2^v	0.95	2.37	3.1944 (15)	146
C18—H18···O3^vi	0.95	2.55	3.2644 (15)	132

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

4-(4-Nitrophenyl)piperazinium 2,3,4,5,6-pentafluorobenzoate (IV) top

Crystal data top

C₁₀H₁₄N₃O₂⁺·C₇F₅O₂⁻	Z = 2
M_r = 419.31	F(000) = 428
Triclinic, P1	D_x = 1.649 Mg m⁻³
a = 5.9779 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3934 (8) Å	Cell parameters from 9830 reflections
c = 12.9312 (9) Å	θ = 2.8–27.5°
α = 75.754 (2)°	µ = 0.15 mm⁻¹
β = 81.670 (2)°	T = 90 K
γ = 87.717 (2)°	Tablet, pale yellow
V = 844.63 (9) Å³	0.21 × 0.17 × 0.05 mm

Data collection top

Bruker D8 Venture dual source diffractometer	3882 independent reflections
Radiation source: microsource	3456 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.034
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −7→7
T_min = 0.914, T_max = 0.959	k = −14→14
38650 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0359P)² + 0.419P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3882 reflections	Δρ_max = 0.36 e Å⁻³
269 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Extinction correction: SHELXL-2019/2 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Special details top

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

Refinement. Refinement progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

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

	x	y	z	U_iso*/U_eq
O1	0.43180 (17)	0.17458 (10)	−0.07590 (8)	0.0322 (2)
O2	0.41598 (17)	0.36577 (10)	−0.07776 (8)	0.0315 (2)
N1	1.18846 (17)	0.19065 (9)	0.40887 (8)	0.0156 (2)
H1NA	1.080 (3)	0.1911 (13)	0.4679 (12)	0.019*
H1NB	1.331 (3)	0.1841 (13)	0.4282 (12)	0.019*
N2	1.23887 (16)	0.20731 (9)	0.18180 (8)	0.0164 (2)
N3	0.49963 (18)	0.26345 (11)	−0.05166 (8)	0.0241 (2)
C1	1.16518 (19)	0.30898 (10)	0.32993 (9)	0.0170 (2)
H1C	1.215721	0.375464	0.357861	0.020*
H1D	1.004664	0.323501	0.319507	0.020*
C2	1.30775 (19)	0.30694 (11)	0.22310 (9)	0.0178 (2)
H2A	1.290093	0.384788	0.170238	0.021*
H2B	1.469162	0.297174	0.233008	0.021*
C3	1.2830 (2)	0.09221 (11)	0.25697 (9)	0.0178 (2)
H3A	1.445777	0.085880	0.264569	0.021*
H3B	1.244024	0.023963	0.228146	0.021*
C4	1.1436 (2)	0.08444 (10)	0.36671 (9)	0.0175 (2)
H4A	0.980836	0.082092	0.360358	0.021*
H4B	1.181938	0.008818	0.417856	0.021*
C5	1.04949 (19)	0.22037 (11)	0.12889 (9)	0.0153 (2)
C6	0.9588 (2)	0.12034 (11)	0.10325 (9)	0.0182 (2)
H6	1.021849	0.042104	0.126884	0.022*
C7	0.7802 (2)	0.13394 (12)	0.04448 (10)	0.0198 (2)
H7	0.721386	0.065866	0.027385	0.024*
C8	0.68749 (19)	0.24811 (12)	0.01068 (9)	0.0189 (2)
C9	0.7691 (2)	0.34801 (11)	0.03565 (9)	0.0188 (2)
H9	0.702687	0.425476	0.012554	0.023*
C10	0.9478 (2)	0.33452 (11)	0.09439 (9)	0.0174 (2)
H10	1.003224	0.403213	0.111854	0.021*
O3	0.86075 (13)	0.21817 (8)	0.56526 (7)	0.01998 (19)
O4	0.61190 (14)	0.17431 (8)	0.46723 (7)	0.01912 (19)
C11	0.66662 (18)	0.21484 (10)	0.54141 (9)	0.0144 (2)
C12	0.48004 (18)	0.26637 (10)	0.61162 (9)	0.0142 (2)
C13	0.29057 (19)	0.2006 (1)	0.66651 (9)	0.0144 (2)
C14	0.12144 (19)	0.2486 (1)	0.72922 (9)	0.0152 (2)
C15	0.13793 (19)	0.36674 (11)	0.73547 (9)	0.0164 (2)
C16	0.3259 (2)	0.43432 (10)	0.68299 (10)	0.0171 (2)
C17	0.49472 (19)	0.38314 (10)	0.62342 (9)	0.0161 (2)
F1	0.26874 (12)	0.08537 (6)	0.66068 (6)	0.01959 (16)
F2	−0.05531 (12)	0.18192 (6)	0.78430 (6)	0.02050 (16)
F3	−0.02700 (12)	0.41607 (7)	0.79314 (6)	0.02259 (17)
F4	0.34328 (13)	0.54896 (7)	0.69035 (6)	0.02478 (18)
F5	0.67401 (12)	0.45273 (6)	0.57274 (6)	0.02176 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0272 (5)	0.0461 (6)	0.0283 (5)	−0.0045 (4)	−0.0106 (4)	−0.0137 (4)
O2	0.0268 (5)	0.0417 (6)	0.0257 (5)	0.0087 (4)	−0.0111 (4)	−0.0048 (4)
N1	0.0123 (4)	0.0197 (5)	0.0159 (5)	0.0007 (4)	−0.0026 (4)	−0.0061 (4)
N2	0.0159 (5)	0.0176 (5)	0.0165 (5)	−0.0003 (4)	−0.0035 (4)	−0.0052 (4)
N3	0.0183 (5)	0.0382 (7)	0.0158 (5)	0.0003 (4)	−0.0032 (4)	−0.0061 (5)
C1	0.0166 (5)	0.0159 (5)	0.0201 (6)	−0.0007 (4)	−0.0034 (4)	−0.0066 (4)
C2	0.0161 (5)	0.0190 (6)	0.0187 (6)	−0.0038 (4)	−0.0026 (4)	−0.0049 (4)
C3	0.0182 (5)	0.0184 (6)	0.0186 (6)	0.0051 (4)	−0.0053 (4)	−0.0070 (4)
C4	0.0182 (5)	0.0156 (5)	0.0189 (6)	0.0005 (4)	−0.0041 (4)	−0.0040 (4)
C5	0.0140 (5)	0.0193 (6)	0.0121 (5)	−0.0005 (4)	0.0003 (4)	−0.0041 (4)
C6	0.0188 (6)	0.0178 (6)	0.0181 (5)	0.0002 (4)	−0.0020 (4)	−0.0050 (4)
C7	0.0193 (6)	0.0242 (6)	0.0172 (5)	−0.0033 (5)	−0.0012 (4)	−0.0078 (5)
C8	0.0144 (5)	0.0292 (6)	0.0130 (5)	−0.0004 (5)	−0.0024 (4)	−0.0044 (5)
C9	0.0175 (5)	0.0213 (6)	0.0152 (5)	0.0020 (4)	−0.0003 (4)	−0.0015 (4)
C10	0.0177 (5)	0.0179 (6)	0.0164 (5)	−0.0012 (4)	−0.0009 (4)	−0.0045 (4)
O3	0.0124 (4)	0.0296 (5)	0.0211 (4)	0.0009 (3)	−0.0036 (3)	−0.0115 (4)
O4	0.0153 (4)	0.0250 (4)	0.0208 (4)	0.0024 (3)	−0.0047 (3)	−0.0118 (3)
C11	0.0136 (5)	0.0136 (5)	0.0159 (5)	0.0003 (4)	−0.0021 (4)	−0.0032 (4)
C12	0.0131 (5)	0.0164 (5)	0.0141 (5)	0.0010 (4)	−0.0041 (4)	−0.0043 (4)
C13	0.0154 (5)	0.0130 (5)	0.0160 (5)	0.0000 (4)	−0.0051 (4)	−0.0040 (4)
C14	0.0134 (5)	0.0180 (6)	0.0133 (5)	−0.0025 (4)	−0.0017 (4)	−0.0019 (4)
C15	0.0152 (5)	0.0201 (6)	0.0149 (5)	0.0035 (4)	−0.0017 (4)	−0.0069 (4)
C16	0.0192 (6)	0.0138 (5)	0.0205 (6)	0.0002 (4)	−0.0043 (4)	−0.0073 (4)
C17	0.0134 (5)	0.0172 (5)	0.0176 (5)	−0.0032 (4)	−0.0017 (4)	−0.0037 (4)
F1	0.0192 (3)	0.0132 (3)	0.0269 (4)	−0.0020 (3)	−0.0013 (3)	−0.0067 (3)
F2	0.0171 (3)	0.0219 (4)	0.0199 (4)	−0.0052 (3)	0.0037 (3)	−0.0033 (3)
F3	0.0201 (4)	0.0244 (4)	0.0240 (4)	0.0027 (3)	0.0036 (3)	−0.0115 (3)
F4	0.0244 (4)	0.0158 (4)	0.0366 (4)	−0.0012 (3)	−0.0006 (3)	−0.0131 (3)
F5	0.0171 (3)	0.0186 (4)	0.0291 (4)	−0.0062 (3)	0.0024 (3)	−0.0071 (3)

Geometric parameters (Å, º) top

O1—N3	1.2304 (15)	C6—C7	1.3806 (17)
O2—N3	1.2376 (15)	C6—H6	0.9500
N1—C4	1.4922 (15)	C7—C8	1.3866 (18)
N1—C1	1.4926 (15)	C7—H7	0.9500
N1—H1NA	0.929 (15)	C8—C9	1.3814 (18)
N1—H1NB	0.915 (16)	C9—C10	1.3810 (17)
N2—C5	1.3902 (14)	C9—H9	0.9500
N2—C2	1.4638 (14)	C10—H10	0.9500
N2—C3	1.4675 (15)	O3—C11	1.2475 (14)
N3—C8	1.4556 (15)	O4—C11	1.2496 (14)
C1—C2	1.5193 (16)	C11—C12	1.5263 (15)
C1—H1C	0.9900	C12—C17	1.3836 (16)
C1—H1D	0.9900	C12—C13	1.3860 (16)
C2—H2A	0.9900	C13—F1	1.3459 (13)
C2—H2B	0.9900	C13—C14	1.3841 (16)
C3—C4	1.5225 (16)	C14—F2	1.3343 (13)
C3—H3A	0.9900	C14—C15	1.3764 (16)
C3—H3B	0.9900	C15—F3	1.3391 (13)
C4—H4A	0.9900	C15—C16	1.3807 (17)
C4—H4B	0.9900	C16—F4	1.3418 (13)
C5—C10	1.4106 (16)	C16—C17	1.3788 (16)
C5—C6	1.4107 (16)	C17—F5	1.3473 (13)

C4—N1—C1	113.04 (9)	C10—C5—C6	117.61 (10)
C4—N1—H1NA	107.8 (9)	C7—C6—C5	121.27 (11)
C1—N1—H1NA	106.1 (9)	C7—C6—H6	119.4
C4—N1—H1NB	109.5 (9)	C5—C6—H6	119.4
C1—N1—H1NB	109.6 (9)	C6—C7—C8	119.25 (11)
H1NA—N1—H1NB	110.9 (13)	C6—C7—H7	120.4
C5—N2—C2	119.8 (1)	C8—C7—H7	120.4
C5—N2—C3	120.24 (10)	C9—C8—C7	121.24 (11)
C2—N2—C3	108.81 (9)	C9—C8—N3	119.10 (11)
O1—N3—O2	123.20 (11)	C7—C8—N3	119.66 (11)
O1—N3—C8	118.67 (11)	C10—C9—C8	119.56 (11)
O2—N3—C8	118.13 (11)	C10—C9—H9	120.2
N1—C1—C2	109.46 (9)	C8—C9—H9	120.2
N1—C1—H1C	109.8	C9—C10—C5	121.06 (11)
C2—C1—H1C	109.8	C9—C10—H10	119.5
N1—C1—H1D	109.8	C5—C10—H10	119.5
C2—C1—H1D	109.8	O3—C11—O4	126.84 (11)
H1C—C1—H1D	108.2	O3—C11—C12	115.21 (10)
N2—C2—C1	110.54 (9)	O4—C11—C12	117.95 (10)
N2—C2—H2A	109.5	C17—C12—C13	116.73 (10)
C1—C2—H2A	109.5	C17—C12—C11	120.47 (10)
N2—C2—H2B	109.5	C13—C12—C11	122.8 (1)
C1—C2—H2B	109.5	F1—C13—C14	117.97 (10)
H2A—C2—H2B	108.1	F1—C13—C12	119.72 (10)
N2—C3—C4	110.32 (9)	C14—C13—C12	122.31 (10)
N2—C3—H3A	109.6	F2—C14—C15	119.71 (10)
C4—C3—H3A	109.6	F2—C14—C13	121.1 (1)
N2—C3—H3B	109.6	C15—C14—C13	119.19 (10)
C4—C3—H3B	109.6	F3—C15—C14	120.17 (10)
H3A—C3—H3B	108.1	F3—C15—C16	119.85 (10)
N1—C4—C3	110.66 (9)	C14—C15—C16	119.98 (10)
N1—C4—H4A	109.5	F4—C16—C17	120.49 (10)
C3—C4—H4A	109.5	F4—C16—C15	119.94 (10)
N1—C4—H4B	109.5	C17—C16—C15	119.57 (11)
C3—C4—H4B	109.5	F5—C17—C16	117.56 (10)
H4A—C4—H4B	108.1	F5—C17—C12	120.25 (10)
N2—C5—C10	121.43 (10)	C16—C17—C12	122.14 (11)
N2—C5—C6	120.9 (1)

C4—N1—C1—C2	−52.11 (12)	O4—C11—C12—C17	−124.65 (12)
C5—N2—C2—C1	80.27 (13)	O3—C11—C12—C13	−124.39 (12)
C3—N2—C2—C1	−63.65 (12)	O4—C11—C12—C13	55.62 (15)
N1—C1—C2—N2	58.10 (12)	C17—C12—C13—F1	−178.3 (1)
C5—N2—C3—C4	−81.76 (12)	C11—C12—C13—F1	1.44 (16)
C2—N2—C3—C4	61.97 (12)	C17—C12—C13—C14	0.83 (16)
C1—N1—C4—C3	51.34 (12)	C11—C12—C13—C14	−179.43 (10)
N2—C3—C4—N1	−55.67 (12)	F1—C13—C14—F2	1.56 (16)
C2—N2—C5—C10	13.05 (16)	C12—C13—C14—F2	−177.59 (10)
C3—N2—C5—C10	152.87 (10)	F1—C13—C14—C15	−179.14 (10)
C2—N2—C5—C6	−170.03 (10)	C12—C13—C14—C15	1.72 (17)
C3—N2—C5—C6	−30.21 (15)	F2—C14—C15—F3	−2.64 (16)
N2—C5—C6—C7	−175.64 (11)	C13—C14—C15—F3	178.05 (10)
C10—C5—C6—C7	1.39 (17)	F2—C14—C15—C16	176.77 (10)
C5—C6—C7—C8	−0.41 (18)	C13—C14—C15—C16	−2.54 (17)
C6—C7—C8—C9	−0.66 (18)	F3—C15—C16—F4	0.33 (17)
C6—C7—C8—N3	179.78 (10)	C14—C15—C16—F4	−179.08 (10)
O1—N3—C8—C9	178.16 (11)	F3—C15—C16—C17	−179.76 (10)
O2—N3—C8—C9	−1.79 (16)	C14—C15—C16—C17	0.83 (17)
O1—N3—C8—C7	−2.27 (17)	F4—C16—C17—F5	−0.70 (17)
O2—N3—C8—C7	177.78 (11)	C15—C16—C17—F5	179.4 (1)
C7—C8—C9—C10	0.68 (17)	F4—C16—C17—C12	−178.25 (10)
N3—C8—C9—C10	−179.75 (10)	C15—C16—C17—C12	1.85 (18)
C8—C9—C10—C5	0.35 (17)	C13—C12—C17—F5	179.89 (10)
N2—C5—C10—C9	175.65 (10)	C11—C12—C17—F5	0.15 (16)
C6—C5—C10—C9	−1.36 (17)	C13—C12—C17—C16	−2.62 (17)
O3—C11—C12—C17	55.33 (15)	C11—C12—C17—C16	177.63 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O3	0.929 (15)	1.754 (16)	2.6723 (13)	169.4 (14)
N1—H1NB···O4ⁱ	0.915 (16)	1.816 (16)	2.7310 (13)	178.8 (14)
C1—H1C···F5ⁱⁱ	0.99	2.49	3.4813 (14)	177
C1—H1D···F4ⁱⁱⁱ	0.99	2.49	3.3996 (14)	153
C4—H4B···O3^iv	0.99	2.56	3.3421 (15)	136
C6—H6···F2^v	0.95	2.54	3.4536 (15)	161

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

Acknowledgements

One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.

Funding information

Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer).

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Volume 79| Part 3| March 2023| Pages 151-156

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

Syntheses and crystal structures of four 4-(4-nitro­phen­yl)piperazinium salts with hydrogen succinate, 4-amino­benzoate, 2-(4-chloro­phen­yl)acetate and 2,3,4,5,6-penta­fluoro­benzoate anions

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis, crystallization and spectroscopic details

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Syntheses and crystal structures of four 4-(4-nitrophenyl)piperazinium salts with hydrogen succinate, 4-aminobenzoate, 2-(4-chlorophenyl)acetate and 2,3,4,5,6-pentafluorobenzoate anions

3. Supramolecular features