dl-Piperidinium-2-carboxyl­ate bis­(hydrogen peroxide): unusual hydrogen-bonded peroxide chains

Navasardyan, M.A.; Grishanov, D.A.; Prikhodchenko, P.V.; Churakov, A.V.

doi:10.1107/S205698902000972X

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Volume 76| Part 8| August 2020| Pages 1331-1335

https://doi.org/10.1107/S205698902000972X

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DL-Piperidinium-2-carboxylate bis(hydrogen peroxide): unusual hydrogen-bonded peroxide chains

Mger A. Navasardyan,^a Dmitry A. Grishanov,^a Petr V. Prikhodchenko ^a and Andrei V. Churakov ^a ^*

^aInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation
^*Correspondence e-mail: churakov@igic.ras.ru

Edited by L. Fabian, University of East Anglia, England (Received 27 May 2020; accepted 16 July 2020; online 21 July 2020)

The title compound, C₆H₁₁NO₂·2H₂O₂, is the richest (by molar ratio) in hydrogen peroxide among the peroxosolvates of aliphatic α-amino acids. The asymmetric unit contains a zwitterionic pipecolinic acid molecule and two hydrogen peroxide molecules. The two crystallographically independent hydrogen peroxide molecules form a different number of hydrogen bonds: one forms two as donor and two as acceptor ([2,2] mode) and the other forms two as donor and one as acceptor ([2,1] mode). The latter hydrogen peroxide molecule forms infinite hydrogen-bonded hydroperoxo chains running along the c-axis direction, which is unusual for aliphatic α-amino acid peroxosolvates.

Keywords: peroxosolvates; aliphatic amino acids; charge assisted hydrogen bonds; peroxide H-bonded chains; carboxylate anions; crystal structure.

CCDC reference: 2016846

1. Chemical context

Peroxosolvates are crystalline adducts of hydrogen peroxide with various organic or inorganic compounds. Since they are convenient solid sources of active oxygen, some of them have become widely used commercial bleaching, disinfection and oxidation reagents (Jakob et al., 2012 ; Cronin et al., 2017 ). It is well known that their stability is strongly dependent on the hydrogen-bonded motifs formed by hydrogen peroxide (Chernyshov et al., 2017 ). On other hand, H₂O₂ is one of the most important signalling molecules in biological systems (Li et al., 2020 ; To et al., 2020 ). The structures of amino acid peroxosolvates have been studied intensively as simple models of hydrogen peroxide binding with proteins (Prikhodchenko et al., 2011 ; Kapustin et al., 2014 ). Peroxide and water–peroxide clusters are now of special interest since they may simulate cooperative hydrogen-bonded switching in the transportation of hydrogen peroxide species through cell membranes (Grishanov et al., 2017 ; Varadaraj & Kumari, 2020 ; Wang et al., 2020 ). Recently, several structures of organic peroxosolvates with peroxide hydrogen-bonded 1D-aggregates have been reported (Chernyshov et al., 2017; Navasardyan et al., 2017 , 2018 ).

2. Structural commentary

The asymmetric unit of the title compound (I) comprises a pipecolinic acid molecule and two crystallographically independent peroxide molecules (Fig. 1). As expected, the amino acid coformer exhibits the zwitterionic form with almost equal C—O distances [1.2429 (11) and 1.2639 (11) Å]. All bond lengths and angles in the organic coformer are close to those observed in the structures of pure pipecolinic acid [(II); Stapleton & Tiekink, 2001 ) and pipecolinic acid tetrahydrate [(III); Bhattacharjee & Chacko, 1979 ; Lyssenko et al., 2006 ]. As observed for (II) and (III), the pipecolinic acid molecule in (I) adopts a chair conformation with the carboxylate group occupying the equatorial position. It is of interest to note in all three structures (I), (II), and (III), the core amino acid fragments N—C—CO₂ are almost planar, with N—C—C—O torsion angles of less than 22°. This is obviously caused by electrostatic interactions between the oppositely charged amino and carboxylic groups.

Figure 1
The asymmetric unit of (I)

with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.

3. Supramolecular features

In the crystal, the organic molecule acts as a donor of two N⁺—H⋯OHOH, and as an acceptor of three COO⁻⋯HOOH hydrogen bonds (Table 1, Fig. 2). The O—O bond lengths [1.4600 (9) and 1.4646 (11) Å] are typical for amino acid peroxosolvates (mean value of 1.465 Å according to the latest, March 2020 version of the CSD; Groom et al., 2016 ). Both crystallographically independent peroxide molecules occupy general positions and adopt skew conformations with H—O—O—H torsion angles of 102.5 (15) and −105.1 (15)°. It is well known that peroxide molecules always form at least two donor hydrogen bonds in the structures of organic peroxosolvates (Chernyshov et al., 2017) and compound (I) is no exception. However, the symmetry-independent peroxide molecules in (I) form a different total number of hydrogen bonds: two donor HOOH⋯⁻O₂C and two acceptor N⁺—H⋯OHOH for H3—O3—O4—H4 ([2,2] mode; Table 1, Fig. 3) and two donor HOOH⋯⁻O₂C and HOOH⋯OHOH together with one acceptor for H5—O5—O6—H6 ([2,1] mode; Table 1, Fig. 4). The occurrence of interperoxide hydrogen-bonds results in the formation of simple infinite hydrogen-bonded `hydroperoxo'-linked chains (Grishanov et al., 2017), running along the c-axis direction (Fig. 5). It is significant that such chains and HOOH⋯OHOH hydrogen bonds were not observed previously in the structures of aliphatic α-amino acid peroxosolvates. The reason for this is that charge-assisted HOOH⋯⁻O₂C bonds are energetically preferable to HOOH⋯OHOH interactions (Jesus & Redinha, 2011 ; Zick & Geiger, 2018 ). For example, in (I) the only interperoxide hydrogen-bond O5—H5⋯O6 is noticeably longer [2.778 (1) Å] than the three HOOH⋯⁻O₂C bonds [2.641 (1)–2.749 (1) Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.872 (17)	1.819 (17)	2.6463 (10)	157.8 (15)
O4—H4⋯O2ⁱ	0.866 (18)	1.889 (18)	2.7490 (10)	172.2 (15)
O6—H6⋯O1	0.881 (16)	1.760 (16)	2.6412 (10)	177.4 (14)
O5—H5⋯O6ⁱⁱ	0.883 (17)	1.898 (18)	2.7777 (12)	174.4 (15)
N1—H1⋯O3ⁱⁱⁱ	0.912 (15)	1.961 (15)	2.8336 (11)	159.6 (13)
N1—H2⋯O4^iv	0.875 (15)	2.112 (15)	2.9459 (11)	159.1 (12)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) -x+1, -y+1, -z+1.

Figure 2
Pipecolinic acid with neighbouring hydrogen-bonded molecules. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (iii) −1 + x, y, z; (iv) 1 − x, 1 − y, 1 − z; (v) 1 − x, 1 − y, −z.]

Figure 3
Hydrogen bonds formed by the peroxide molecule H3—O3—O4—H4. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) 1 − x, 1 − y, −z; (vi) 1 + x, y, z; (vii) 1 − x, 1 − y, 1 − z.]

Figure 4
Hydrogen bonds formed by peroxide molecule H5—O5—O6—H6. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (ii) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z; (viii) x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z.]

Figure 5
Peroxide hydrogen-bonded chains parallel to the c axis. Hydrogen bonds are shown as dashed lines.

4. Database survey

Aliphatic α-amino acids contain side chains without heteroatoms suitable for hydrogen-bonding. Up to date, six structures of their peroxosolvates are known: monoperoxosolvates of N,N-dimethylglycine (C₄H₉NO₂; Kapustin et al., 2014), N-methylglycine (sarcosine) (C₃H₇NO₂; Navasardyan et al., 2017), isoleucine (C₆H₁₃NO₂; Prikhodchenko et al., 2011); sesquiperoxosolvates of glycine (C₂H₅NO₂), DL-2-aminobutyric acid (C₄H₉NO₂) and L-phenylalanine (C₉H₁₁NO₂; Prikhodchenko et al., 2011). In all of these structures, the organic molecules exist as zwitterions and all peroxide hydrogen atoms are involved in charge-assisted hydrogen-bonds with the carboxylate groups. All peroxide molecules adopt skew conformations with H—O—O—H torsion angles varying between 88.6 and 166.3°.

The carboxylate anions possess four sp²-hybridized lone electron pairs suitable for hydrogen-bond formation (Fig. 6) (Mills & Dean, 1996 ). It is well known that syn and anti lone pairs exhibit noticeably different basicity (Gandour, 1981 ; Pal et al., 2018 ) and hydrogen-bonding properties as a result of electronic and steric effects (Gorbitz & Etter, 1992 ; Pranata, 1993 ). Nine hydrogen-bonded linkage modes are theoretically possible in the structures of amino acid peroxosolvates, taking into account that bifurcated HOOH⋯O bonds are not known (Fig. 7). The two simplest modes [0;S] and [0;A] have not been observed in peroxosolvates of α-amino acids, since the peroxide/acid molar ratio is greater than or equal to 1 in each reported structure. The [S;S] linkage was observed in sarcosine monoperoxosolvate. The [S;A] mode was found for the N,N-dimethylglycine and isoleucine monosolvates. Examples of neither the [0;SA] nor the [A;A] case are currently known. As for three hydrogen bonds, both [S;SA] and [SA;A] linkages were found in the sesquiperoxosolvate structures of glycine, DL-2-aminobutyric acid and L-phenylalanine. Following the same logic, we expected to find [SA;SA] in the structure of the title diperoxosolvate (I). However, the triple hydrogen-bonded case [S;SA] occurred, with the fourth donor hydrogen bond HOOH⋯O engaged in forming hydrogen-bonded peroxide chains. It has been shown that the ability of carboxylic anti-orbitals to form hydrogen bonds is strongly affected by steric hindrance caused by β-substituents in the side chains of carboxylic acids (Gorbitz & Etter, 1992). It is clear that in (I) the unfeasibility of the fourth carboxylic hydrogen bond is the result of steric effects caused by the peroxide molecules hydrogen bonded with the ammonium group (Fig. 2). It should be noted that the spatial arrangement of the endocyclic amino group in (I) is predefined by the aforementioned planarity of the N—C—CO₂ amino acid fragment.

Figure 6
The mutual arrangement of syn and anti lone electron pairs of the carboxylate anion.

Figure 7
Possible hydrogen-bonded motifs in the structures of amino acid peroxosolvates.

5. Synthesis and crystallization

96% Hydrogen peroxide was prepared by an extraction method from serine peroxosolvate (Wolanov et al., 2010 ). Colourless prismatic crystals of the title compound were obtained by cooling a saturated solution (r.t.) of pipecolinic acid (Aldrich) in 96% hydrogen peroxide to 255 K. Handling procedures for concentrated hydrogen peroxide have been described in detail (danger of explosion!) by Schumb et al. (1955 ).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All hydrogen atoms were found in difference-Fourier maps and were refined with independent positional and isotropic displacement parameters.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₁NO₂·2H₂O₂
M_r	197.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	6.5739 (4), 22.9278 (15), 6.0647 (4)
β (°)	93.770 (1)
V (Å³)	912.12 (10)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.13
Crystal size (mm)	0.50 × 0.50 × 0.50

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.659, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	9809, 2418, 2170
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.084, 1.08
No. of reflections	2418
No. of parameters	178
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.19
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXL2018/3 (Sheldrick, 2015 ) and XP in SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2016846

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902000972X/fy2147sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902000972X/fy2147Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008).

DL-Piperidinium-2-carboxylate bis(hydrogen peroxide) top

Crystal data top

C₆H₁₁NO₂·2H₂O₂	F(000) = 424
M_r = 197.19	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.5739 (4) Å	Cell parameters from 5232 reflections
b = 22.9278 (15) Å	θ = 3.1–30.6°
c = 6.0647 (4) Å	µ = 0.13 mm⁻¹
β = 93.770 (1)°	T = 150 K
V = 912.12 (10) Å³	Nugget, colourless
Z = 4	0.50 × 0.50 × 0.50 mm

Data collection top

Bruker SMART APEXII diffractometer	2170 reflections with I > 2σ(I)
ω scans	R_int = 0.018
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 29.0°, θ_min = 3.1°
T_min = 0.659, T_max = 0.746	h = −8→8
9809 measured reflections	k = −30→31
2418 independent reflections	l = −8→8

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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.084	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0419P)² + 0.218P] where P = (F_o² + 2F_c²)/3
2418 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq
N1	−0.02450 (12)	0.57964 (3)	0.57611 (13)	0.01528 (16)
H1	−0.093 (2)	0.5604 (6)	0.463 (2)	0.029 (3)*
H2	0.039 (2)	0.5538 (6)	0.661 (2)	0.025 (3)*
O1	0.40875 (11)	0.60608 (3)	0.25095 (12)	0.02266 (17)
O2	0.21298 (11)	0.52860 (3)	0.30218 (11)	0.02005 (16)
C1	−0.17311 (14)	0.61336 (4)	0.70359 (15)	0.01777 (18)
H11	−0.2642 (19)	0.5851 (6)	0.759 (2)	0.021 (3)*
H12	−0.2449 (19)	0.6384 (6)	0.597 (2)	0.024 (3)*
C2	−0.05768 (15)	0.64708 (4)	0.88702 (15)	0.01993 (19)
H21	−0.157 (2)	0.6679 (6)	0.968 (2)	0.029 (3)*
H22	0.010 (2)	0.6192 (6)	0.988 (2)	0.029 (3)*
C3	0.10082 (16)	0.68727 (4)	0.79508 (17)	0.0218 (2)
H32	0.033 (2)	0.7172 (6)	0.703 (2)	0.027 (3)*
H31	0.179 (2)	0.7082 (6)	0.916 (2)	0.030 (3)*
C4	0.24769 (14)	0.65223 (4)	0.66075 (16)	0.01923 (19)
H41	0.343 (2)	0.6784 (6)	0.590 (2)	0.027 (3)*
H42	0.326 (2)	0.6256 (6)	0.759 (2)	0.027 (3)*
C5	0.13006 (13)	0.61800 (4)	0.47837 (14)	0.01483 (17)
H52	0.0520 (18)	0.6451 (5)	0.377 (2)	0.019 (3)*
C6	0.26188 (13)	0.58042 (4)	0.33422 (14)	0.01570 (18)
O3	0.74598 (11)	0.54761 (3)	0.18291 (11)	0.01986 (16)
O4	0.72361 (11)	0.48529 (3)	0.13828 (12)	0.02162 (16)
H4	0.737 (2)	0.4839 (7)	−0.003 (3)	0.040 (4)*
H3	0.620 (3)	0.5583 (7)	0.194 (3)	0.040 (4)*
O5	0.67290 (12)	0.72538 (4)	0.33260 (14)	0.02787 (18)
O6	0.49801 (12)	0.71623 (3)	0.17405 (13)	0.02507 (17)
H5	0.613 (2)	0.7454 (7)	0.434 (3)	0.041 (4)*
H6	0.472 (2)	0.6792 (7)	0.199 (2)	0.034 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0163 (3)	0.0143 (4)	0.0153 (3)	−0.0005 (3)	0.0025 (3)	−0.0015 (3)
O1	0.0229 (4)	0.0170 (3)	0.0293 (4)	−0.0015 (3)	0.0110 (3)	−0.0023 (3)
O2	0.0237 (3)	0.0149 (3)	0.0221 (3)	−0.0016 (2)	0.0060 (3)	−0.0044 (2)
C1	0.0169 (4)	0.0183 (4)	0.0185 (4)	0.0023 (3)	0.0044 (3)	−0.0002 (3)
C2	0.0237 (5)	0.0202 (4)	0.0163 (4)	0.0037 (4)	0.0042 (3)	−0.0023 (3)
C3	0.0251 (5)	0.0179 (4)	0.0225 (5)	−0.0009 (4)	0.0036 (4)	−0.0074 (4)
C4	0.0186 (4)	0.0182 (4)	0.0211 (4)	−0.0024 (3)	0.0023 (3)	−0.0057 (3)
C5	0.0165 (4)	0.0132 (4)	0.0150 (4)	−0.0002 (3)	0.0028 (3)	−0.0004 (3)
C6	0.0170 (4)	0.0162 (4)	0.0140 (4)	0.0019 (3)	0.0018 (3)	−0.0012 (3)
O3	0.0193 (3)	0.0172 (3)	0.0229 (3)	0.0006 (3)	0.0008 (3)	−0.0044 (2)
O4	0.0301 (4)	0.0158 (3)	0.0187 (3)	0.0029 (3)	0.0003 (3)	−0.0012 (2)
O5	0.0261 (4)	0.0308 (4)	0.0265 (4)	−0.0044 (3)	0.0001 (3)	−0.0053 (3)
O6	0.0308 (4)	0.0200 (4)	0.0237 (4)	−0.0027 (3)	−0.0029 (3)	0.0024 (3)

Geometric parameters (Å, º) top

N1—C5	1.4955 (11)	C3—H32	0.974 (14)
N1—C1	1.4996 (11)	C3—H31	0.991 (14)
N1—H1	0.912 (15)	C4—C5	1.5247 (12)
N1—H2	0.875 (15)	C4—H41	0.986 (14)
O1—C6	1.2639 (11)	C4—H42	0.975 (14)
O2—C6	1.2429 (11)	C5—C6	1.5353 (12)
C1—C2	1.5166 (13)	C5—H52	0.991 (12)
C1—H11	0.958 (13)	O3—O4	1.4600 (9)
C1—H12	0.966 (13)	O3—H3	0.872 (17)
C2—C3	1.5239 (14)	O4—H4	0.866 (18)
C2—H21	0.968 (14)	O5—O6	1.4646 (11)
C2—H22	0.972 (14)	O5—H5	0.883 (17)
C3—C4	1.5313 (13)	O6—H6	0.881 (16)

C5—N1—C1	112.57 (7)	C4—C3—H31	109.3 (8)
C5—N1—H1	107.6 (9)	H32—C3—H31	106.3 (11)
C1—N1—H1	109.2 (9)	C5—C4—C3	110.40 (8)
C5—N1—H2	108.7 (9)	C5—C4—H41	107.7 (8)
C1—N1—H2	110.4 (9)	C3—C4—H41	110.7 (8)
H1—N1—H2	108.2 (12)	C5—C4—H42	110.0 (8)
N1—C1—C2	109.24 (7)	C3—C4—H42	109.4 (8)
N1—C1—H11	106.0 (8)	H41—C4—H42	108.6 (11)
C2—C1—H11	112.4 (8)	N1—C5—C4	109.91 (7)
N1—C1—H12	105.4 (8)	N1—C5—C6	108.62 (7)
C2—C1—H12	112.9 (8)	C4—C5—C6	115.06 (7)
H11—C1—H12	110.4 (11)	N1—C5—H52	106.0 (7)
C1—C2—C3	111.17 (8)	C4—C5—H52	110.1 (7)
C1—C2—H21	107.6 (8)	C6—C5—H52	106.7 (7)
C3—C2—H21	112.8 (8)	O2—C6—O1	125.38 (8)
C1—C2—H22	108.3 (8)	O2—C6—C5	118.40 (8)
C3—C2—H22	109.6 (8)	O1—C6—C5	116.16 (8)
H21—C2—H22	107.3 (11)	O4—O3—H3	101.8 (11)
C2—C3—C4	110.34 (8)	O3—O4—H4	101.7 (10)
C2—C3—H32	109.7 (8)	O6—O5—H5	99.6 (11)
C4—C3—H32	110.2 (8)	O5—O6—H6	100.4 (10)
C2—C3—H31	111.0 (8)

C5—N1—C1—C2	−58.48 (10)	C3—C4—C5—C6	−179.22 (8)
N1—C1—C2—C3	56.95 (10)	N1—C5—C6—O2	6.85 (11)
C1—C2—C3—C4	−56.65 (11)	C4—C5—C6—O2	130.51 (9)
C2—C3—C4—C5	55.85 (11)	N1—C5—C6—O1	−175.64 (8)
C1—N1—C5—C4	58.51 (10)	C4—C5—C6—O1	−51.98 (11)
C1—N1—C5—C6	−174.80 (7)	H3—O3—O4—H4	102.5 (15)
C3—C4—C5—N1	−56.25 (10)	H5—O5—O6—H6	−105.1 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.872 (17)	1.819 (17)	2.6463 (10)	157.8 (15)
O4—H4···O2ⁱ	0.866 (18)	1.889 (18)	2.7490 (10)	172.2 (15)
O6—H6···O1	0.881 (16)	1.760 (16)	2.6412 (10)	177.4 (14)
O5—H5···O6ⁱⁱ	0.883 (17)	1.898 (18)	2.7777 (12)	174.4 (15)
N1—H1···O3ⁱⁱⁱ	0.912 (15)	1.961 (15)	2.8336 (11)	159.6 (13)
N1—H2···O4^iv	0.875 (15)	2.112 (15)	2.9459 (11)	159.1 (12)

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

Acknowledgements

X-ray diffraction studies were performed at the Centre of Shared Equipment of IGIC RAS.

Funding information

Funding for this research was provided by: Russian Foundation for Basic Research (award No. 20-03-00449).

References

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