2-Hy­droxy­ethyl­ammonium [2-(2,6-di­chloro­anilino)phen­yl]acetate monohydrate

Obidova, N.; Ashurov, J.; Izotova, L.; Ibragimov, B.

doi:10.1107/S2414314622004412

organic compounds

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ISSN: 2414-3146

Volume 7| Part 4| April 2022| x220441

https://doi.org/10.1107/S2414314622004412

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2-Hydroxyethylammonium [2-(2,6-dichloroanilino)phenyl]acetate monohydrate

Nodira Obidova,^a Jamshid Ashurov,^a Lidiya Izotova ^a ^* and Bakhtiyar Ibragimov ^a

^aInstitute of Bioorganic Chemistry, UzAS, M. Ulugbek Str., 83, 100125, Tashkent, Uzbekistan
^*Correspondence e-mail: li_izotova@mail.ru

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 24 March 2022; accepted 26 April 2022; online 28 April 2022)

In the solid-state structure of the title compound derived from diclofenac, C₂H₈NO⁺·C₁₄H₁₀Cl₂NO₂⁻·H₂O, the asymmetric unit contains one cation, one anion and a water molecule, all in general positions. A complex network of hydrogen bonds is present in the crystal structure.

Keywords: crystal structure; diclofenac; complex; hydrogen bonding..

CCDC reference: 2168795

Structure description

The pharmaceutical diclofenac (D) is widely used as a non-steroidal anti-inflammatory drug, to treat pain and inflammatory diseases (Skoutakis et al., 1988 ; Moser et al., 1990 ). The Cambridge Structural Database (CSD version 5.42, last update February 2021; Groom et al., 2016 ) includes crystallographic data for 50 entries with the term `diclofenac'. Among them, there are 21 entries where diclofenac is present in the form of a salt, and in three entries, diclofenac forms salts with aliphatic amines: with (R) and (S)-phenylethylammonium (Lemmerer et al., 2010 ), with diethyl ammonium (Castellari et al., 2001 ) and with tris(2-ammonioethyl)amine (Lynch et al., 2003 ). In this article, we present another complex in the form of a diclofenac salt with an amino-containing compound, namely monoethanolamine. Ethanolamine is always present in significant quantities in the human and animal body with a complete protein diet. Its formation occurs during the decarboxylation of serine, and in one of the metabolic variants, it turns into glycine (the simplest aliphatic amino acid; Wishart et al., 2007 ). In addition, monoethanolamine is used in some cosmetic products (Knaak et al., 1997 ). Therefore, the interaction of these compounds seems to be interesting for investigation.

The crystal structure of the title compound has one monoethanolamine (MEA) cation, one 2-(2,6-dichloroanilino)phenyl acetic acid or diclofenac (D) anion, and one water molecule in the asymmetric unit, and crystallizes in space group P2₁/c (Fig. 1). The diclofenac anion is stabilized by one intramolecular hydrogen bond between the amino group and atom O1 of the carboxylic group: N1—H1⋯O1 [2.884 (3) Å, 128.9°; see Table 1], which forms a seven-membered ring with graph-set notation S(7) (Etter, 1990 ). The dihedral angle between the two benzene rings in D is 60.2 (2)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.27	2.884 (3)	129
N2—H2A⋯O2ⁱ	0.89	1.96	2.811 (4)	160
N2—H2B⋯O1Wⁱⁱ	0.89	2.15	2.947 (4)	148
N2—H2C⋯O1ⁱⁱⁱ	0.89	1.92	2.802 (3)	169
O3—H3A⋯O1W	0.82	1.96	2.770 (4)	168
O1W—H1WB⋯O2	0.85	1.87	2.690 (3)	161
O1W—H1WA⋯O1^iv	0.85	2.00	2.809 (3)	158
Symmetry codes: (i) ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) ; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
Perspective view of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at 40% probability level. The dashed lines represent hydrogen bonds within the asymmetric unit.

The ionic form of the title compound serves as a building block for the supramolecular architecture. In the crystal, the building blocks form screw-like chains along the b-axis direction, due to the crystallographic twofold screw axis, via N2—H2B⋯O1Wⁱⁱ hydrogen bond [2.947 (4) Å, symmetry code: (ii) −x, y − $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; Fig. 2 and Table 1]. The chains are further consolidated into two-dimensional layers through N—H⋯O and O—H⋯O hydrogen bonds. These layers propagate parallel to the (100) plane, where the chains are related by the glide plane c [O1W⋯O1^iv, symmetry code: (iv) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; 2.809 (3) Å] and the inversion centre [N2... O2ⁱ, symmetry code: (i) −x, −y + 1, −z + 1, 2.811 (4) Å, Fig. 2]. The layers are linked by Y—X⋯Cg π–ring interactions, for C3—H3 and C7—Cl1 bonds, for which the X⋯Cg separations and γ angles range from 3.533 to 3.958 Å and from 25.03 to 28.79°.

Figure 2
Packing diagram of the title compound, viewed down b axis. The hydrogen bonds are shown as dashed lines.

In order to visualize the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface analysis was carried out using Crystal Explorer 17.5 (Turner et al., 2017 ). The Hirshfeld surface mapped over d_norm shows the expected bright-red spots near atoms O1 and O2, involved in the O—H⋯O and N—H⋯O hydrogen-bonding interactions (Fig. 3). Fingerprint plots (Fig. 4) reveal that H⋯H, H⋯C/C⋯H, H⋯Cl/Cl⋯H and H⋯O/O⋯H interactions make the greatest contributions to the surface contacts (Table 1), while H⋯N/N⋯H, C⋯C and O⋯O contacts are much less significant.

Figure 3
The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (31.0%), H⋯C/C⋯H (26.3%) and H⋯Cl/Cl⋯H (25%) interactions.

Figure 4
Full two-dimensional fingerprint plots for the title compound, showing all interactions (a), and delineated into (b) H⋯H, (c) H⋯C/C⋯H, (d) H⋯Cl/Cl⋯H, (e) H⋯O/O⋯H, (f) H⋯N/N⋯H, (g) C⋯C and (h) O⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from a given point on the Hirshfeld surface depicted in Fig. 3

Synthesis and crystallization

To a solution of 0.1 g (0.52 mmol) of D in 4 ml of ethanol, 32 µL of monoethanolamine was added. The mixture was kept in an ultrasonic bath (30 kHz) at 298 K for 5 min. The solution was then placed in a loosely closed bottle and kept at 298 K for 10 days. The precipitated prismatic crystals were selected for the single-crystal X-ray diffraction analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂H₈NO⁺·C₁₄H₁₀Cl₂NO₂⁻·H₂O
M_r	375.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	19.1257 (10), 9.3864 (5), 10.0502 (6)
β (°)	103.546 (6)
V (Å³)	1754.05 (17)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.53
Crystal size (mm)	0.31 × 0.28 × 0.1

Data collection
Diffractometer	Agilent Technologies Xcalibur, Ruby
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.356, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12416, 3621, 2431
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.134, 1.01
No. of reflections	3621
No. of parameters	222
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), XP (Siemens, 1994 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2168795

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622004412/bh4068sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622004412/bh4068Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622004412/bh4068Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP (Siemens, 1994), Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

2-Hydroxyethylammonium [2-(2,6-dichloroanilino)phenyl]acetate monohydrate top

Crystal data top

C₂H₈NO⁺·C₁₄H₁₀Cl₂NO₂⁻·H₂O	F(000) = 784
M_r = 375.24	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 19.1257 (10) Å	Cell parameters from 2166 reflections
b = 9.3864 (5) Å	θ = 4.7–73.9°
c = 10.0502 (6) Å	µ = 3.53 mm⁻¹
β = 103.546 (6)°	T = 293 K
V = 1754.05 (17) Å³	Prism, colourless
Z = 4	0.31 × 0.28 × 0.1 mm

Data collection top

Agilent Technologies Xcalibur, Ruby diffractometer	2431 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
/w scans	θ_max = 76.5°, θ_min = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −23→24
T_min = 0.356, T_max = 1.000	k = −11→6
12416 measured reflections	l = −12→12
3621 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: mixed
wR(F²) = 0.134	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0614P)²] where P = (F_o² + 2F_c²)/3
3621 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Refinement. All hydrogen atoms were placed in idealized positions and refined as riding to their carrier atoms.

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

	x	y	z	U_iso*/U_eq
Cl1	0.46202 (4)	0.95109 (8)	0.76764 (8)	0.0441 (2)
Cl2	0.24250 (4)	1.20690 (9)	0.40514 (9)	0.0500 (2)
O1	0.15000 (11)	0.9926 (2)	0.5897 (2)	0.0472 (6)
O1W	0.07192 (13)	0.6316 (3)	0.8457 (2)	0.0558 (6)
H1WA	0.103624	0.612215	0.917982	0.084*
H1WB	0.085392	0.710654	0.818732	0.084*
N1	0.30390 (13)	0.9959 (2)	0.6226 (3)	0.0379 (6)
H1	0.269351	1.041181	0.645204	0.045*
O2	0.08825 (11)	0.8748 (3)	0.7146 (2)	0.0592 (7)
N2	0.03573 (14)	0.1808 (3)	0.4921 (3)	0.0446 (6)
H2A	0.003371	0.148791	0.419647	0.054*
H2B	0.015651	0.187499	0.563284	0.054*
H2C	0.072670	0.120586	0.512028	0.054*
O3	0.07091 (17)	0.3857 (3)	0.6928 (3)	0.0762 (9)
H3A	0.073883	0.464400	0.729146	0.114*
C2	0.42880 (15)	1.0634 (3)	0.6305 (3)	0.0327 (6)
C14	0.14604 (15)	0.9162 (3)	0.6906 (3)	0.0371 (7)
C1	0.35476 (15)	1.0754 (3)	0.5751 (3)	0.0322 (6)
C12	0.26283 (14)	0.7823 (3)	0.7158 (3)	0.0342 (6)
C7	0.30532 (15)	0.8463 (3)	0.6360 (3)	0.0342 (6)
C8	0.34720 (15)	0.7613 (3)	0.5707 (3)	0.0382 (7)
H8	0.374195	0.803323	0.515422	0.046*
C6	0.33381 (16)	1.1786 (3)	0.4739 (3)	0.0359 (6)
C13	0.21653 (15)	0.8708 (3)	0.7865 (3)	0.0383 (7)
H13A	0.243062	0.955166	0.824815	0.046*
H13B	0.206067	0.816317	0.861507	0.046*
C9	0.34871 (16)	0.6146 (3)	0.5877 (3)	0.0447 (8)
H9	0.377768	0.559121	0.546037	0.054*
C5	0.38298 (18)	1.2604 (3)	0.4257 (3)	0.0430 (7)
H5	0.366991	1.328721	0.358405	0.052*
C4	0.45510 (18)	1.2404 (3)	0.4774 (3)	0.0459 (8)
H4	0.488229	1.292653	0.442936	0.055*
C3	0.47873 (16)	1.1423 (3)	0.5811 (3)	0.0408 (7)
H3	0.527698	1.129421	0.617432	0.049*
C11	0.26455 (17)	0.6344 (3)	0.7292 (3)	0.0436 (8)
H11	0.236429	0.590723	0.781473	0.052*
C10	0.30743 (18)	0.5508 (3)	0.6661 (3)	0.0488 (8)
H10	0.308209	0.452307	0.676839	0.059*
C16	0.06160 (19)	0.3234 (3)	0.4609 (4)	0.0515 (8)
H16A	0.020800	0.385304	0.426179	0.062*
H16B	0.088673	0.314490	0.390895	0.062*
C15	0.1082 (2)	0.3869 (4)	0.5871 (4)	0.0593 (10)
H15A	0.152356	0.332453	0.614785	0.071*
H15B	0.120699	0.483999	0.568925	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0413 (4)	0.0418 (4)	0.0442 (4)	0.0030 (3)	0.0002 (3)	0.0044 (3)
Cl2	0.0424 (4)	0.0481 (5)	0.0552 (5)	0.0075 (3)	0.0025 (4)	0.0094 (4)
O1	0.0363 (12)	0.0534 (14)	0.0497 (13)	0.0053 (10)	0.0057 (10)	0.0195 (11)
O1W	0.0600 (15)	0.0558 (16)	0.0496 (15)	−0.0060 (12)	0.0087 (12)	0.0047 (11)
N1	0.0349 (13)	0.0309 (13)	0.0525 (15)	0.0053 (10)	0.0196 (12)	0.0055 (11)
O2	0.0325 (12)	0.0799 (18)	0.0625 (16)	−0.0032 (11)	0.0054 (11)	0.0235 (13)
N2	0.0409 (14)	0.0497 (16)	0.0404 (15)	0.0072 (12)	0.0037 (12)	−0.0030 (12)
O3	0.106 (2)	0.0641 (18)	0.0689 (18)	−0.0190 (17)	0.0403 (17)	−0.0214 (14)
C2	0.0376 (15)	0.0276 (14)	0.0331 (15)	0.0030 (12)	0.0087 (12)	−0.0018 (12)
C14	0.0317 (15)	0.0414 (17)	0.0364 (17)	0.0012 (13)	0.0043 (13)	−0.0003 (13)
C1	0.0351 (15)	0.0267 (14)	0.0347 (15)	0.0014 (11)	0.0080 (12)	−0.0029 (11)
C12	0.0283 (14)	0.0355 (16)	0.0351 (16)	0.0000 (12)	−0.0003 (12)	0.0050 (12)
C7	0.0300 (14)	0.0310 (15)	0.0377 (16)	0.0010 (11)	0.0002 (12)	0.0027 (12)
C8	0.0328 (15)	0.0415 (17)	0.0389 (17)	0.0001 (13)	0.0056 (13)	−0.0017 (13)
C6	0.0373 (15)	0.0322 (15)	0.0374 (16)	0.0013 (12)	0.0071 (13)	−0.0013 (12)
C13	0.0352 (15)	0.0428 (17)	0.0351 (16)	−0.0017 (13)	0.0044 (13)	0.0068 (13)
C9	0.0415 (17)	0.0377 (17)	0.0498 (19)	0.0045 (14)	0.0004 (15)	−0.0099 (15)
C5	0.057 (2)	0.0333 (16)	0.0410 (18)	−0.0019 (14)	0.0157 (16)	0.0027 (13)
C4	0.0494 (19)	0.0401 (18)	0.053 (2)	−0.0111 (15)	0.0226 (17)	−0.0036 (15)
C3	0.0346 (16)	0.0380 (17)	0.0505 (19)	−0.0056 (13)	0.0115 (14)	−0.0067 (14)
C11	0.0441 (18)	0.0387 (17)	0.0447 (19)	−0.0035 (14)	0.0039 (15)	0.0110 (14)
C10	0.052 (2)	0.0313 (16)	0.058 (2)	−0.0001 (14)	0.0025 (17)	0.0041 (15)
C16	0.059 (2)	0.0442 (19)	0.049 (2)	0.0028 (16)	0.0073 (17)	0.0046 (15)
C15	0.055 (2)	0.064 (2)	0.058 (2)	−0.0107 (18)	0.0104 (18)	−0.0099 (19)

Geometric parameters (Å, º) top

Cl1—C2	1.734 (3)	C7—C8	1.398 (4)
Cl2—C6	1.741 (3)	C8—C9	1.387 (4)
O1—C14	1.259 (3)	C8—H8	0.9300
O1W—H1WA	0.8501	C6—C5	1.387 (4)
O1W—H1WB	0.8504	C13—H13A	0.9700
N1—C1	1.396 (3)	C13—H13B	0.9700
N1—C7	1.410 (3)	C9—C10	1.377 (4)
N1—H1	0.8600	C9—H9	0.9300
O2—C14	1.248 (3)	C5—C4	1.368 (5)
N2—C16	1.486 (4)	C5—H5	0.9300
N2—H2A	0.8900	C4—C3	1.384 (4)
N2—H2B	0.8900	C4—H4	0.9300
N2—H2C	0.8900	C3—H3	0.9300
O3—C15	1.412 (4)	C11—C10	1.391 (5)
O3—H3A	0.8200	C11—H11	0.9300
C2—C3	1.389 (4)	C10—H10	0.9300
C2—C1	1.400 (4)	C16—C15	1.494 (5)
C14—C13	1.523 (4)	C16—H16A	0.9700
C1—C6	1.394 (4)	C16—H16B	0.9700
C12—C11	1.395 (4)	C15—H15A	0.9700
C12—C7	1.403 (4)	C15—H15B	0.9700
C12—C13	1.508 (4)

H1WA—O1W—H1WB	104.5	C14—C13—H13A	109.0
C1—N1—C7	124.4 (2)	C12—C13—H13B	109.0
C1—N1—H1	117.8	C14—C13—H13B	109.0
C7—N1—H1	117.8	H13A—C13—H13B	107.8
C16—N2—H2A	109.5	C10—C9—C8	120.3 (3)
C16—N2—H2B	109.5	C10—C9—H9	119.8
H2A—N2—H2B	109.5	C8—C9—H9	119.8
C16—N2—H2C	109.5	C4—C5—C6	119.8 (3)
H2A—N2—H2C	109.5	C4—C5—H5	120.1
H2B—N2—H2C	109.5	C6—C5—H5	120.1
C15—O3—H3A	109.5	C5—C4—C3	120.0 (3)
C3—C2—C1	122.1 (3)	C5—C4—H4	120.0
C3—C2—Cl1	117.0 (2)	C3—C4—H4	120.0
C1—C2—Cl1	120.9 (2)	C4—C3—C2	119.5 (3)
O2—C14—O1	123.9 (3)	C4—C3—H3	120.2
O2—C14—C13	118.9 (3)	C2—C3—H3	120.2
O1—C14—C13	117.2 (3)	C10—C11—C12	121.4 (3)
C6—C1—N1	121.1 (3)	C10—C11—H11	119.3
C6—C1—C2	115.9 (3)	C12—C11—H11	119.3
N1—C1—C2	122.8 (3)	C9—C10—C11	119.6 (3)
C11—C12—C7	118.5 (3)	C9—C10—H10	120.2
C11—C12—C13	120.4 (3)	C11—C10—H10	120.2
C7—C12—C13	121.1 (3)	N2—C16—C15	110.0 (3)
C8—C7—C12	119.7 (3)	N2—C16—H16A	109.7
C8—C7—N1	121.6 (3)	C15—C16—H16A	109.7
C12—C7—N1	118.7 (3)	N2—C16—H16B	109.7
C9—C8—C7	120.4 (3)	C15—C16—H16B	109.7
C9—C8—H8	119.8	H16A—C16—H16B	108.2
C7—C8—H8	119.8	O3—C15—C16	109.2 (3)
C5—C6—C1	122.5 (3)	O3—C15—H15A	109.8
C5—C6—Cl2	118.4 (2)	C16—C15—H15A	109.8
C1—C6—Cl2	119.1 (2)	O3—C15—H15B	109.8
C12—C13—C14	112.7 (2)	C16—C15—H15B	109.8
C12—C13—H13A	109.0	H15A—C15—H15B	108.3

C7—N1—C1—C6	131.3 (3)	C2—C1—C6—Cl2	−176.9 (2)
C7—N1—C1—C2	−52.7 (4)	C11—C12—C13—C14	−100.2 (3)
C3—C2—C1—C6	−4.4 (4)	C7—C12—C13—C14	80.1 (3)
Cl1—C2—C1—C6	174.1 (2)	O2—C14—C13—C12	117.9 (3)
C3—C2—C1—N1	179.4 (3)	O1—C14—C13—C12	−61.2 (4)
Cl1—C2—C1—N1	−2.1 (4)	C7—C8—C9—C10	1.8 (4)
C11—C12—C7—C8	0.9 (4)	C1—C6—C5—C4	0.3 (5)
C13—C12—C7—C8	−179.4 (3)	Cl2—C6—C5—C4	−179.8 (2)
C11—C12—C7—N1	−179.8 (3)	C6—C5—C4—C3	−2.4 (5)
C13—C12—C7—N1	−0.1 (4)	C5—C4—C3—C2	0.9 (5)
C1—N1—C7—C8	−16.6 (4)	C1—C2—C3—C4	2.6 (4)
C1—N1—C7—C12	164.1 (3)	Cl1—C2—C3—C4	−176.0 (2)
C12—C7—C8—C9	−2.0 (4)	C7—C12—C11—C10	0.3 (4)
N1—C7—C8—C9	178.7 (3)	C13—C12—C11—C10	−179.3 (3)
N1—C1—C6—C5	179.3 (3)	C8—C9—C10—C11	−0.5 (5)
C2—C1—C6—C5	3.0 (4)	C12—C11—C10—C9	−0.5 (5)
N1—C1—C6—Cl2	−0.6 (4)	N2—C16—C15—O3	−53.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.27	2.884 (3)	129
N2—H2A···O2ⁱ	0.89	1.96	2.811 (4)	160
N2—H2B···O1Wⁱⁱ	0.89	2.15	2.947 (4)	148
N2—H2C···O1ⁱⁱⁱ	0.89	1.92	2.802 (3)	169
O3—H3A···O1W	0.82	1.96	2.770 (4)	168
O1W—H1WB···O2	0.85	1.87	2.690 (3)	161
O1W—H1WA···O1^iv	0.85	2.00	2.809 (3)	158

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

Funding information

Funding for this research was provided by: Uzbek Academy of Sciences.

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