Crystal structure and Hirshfeld surface analysis of 1-(tert-butyl­amino)-3-mesitylpropan-2-ol hemi­hydrate

Khalilov, A.N.; Khrustalev, V.N.; Tereshina, T.A.; Akkurt, M.; Rzayev, R.M.; Akobirshoeva, A.A.; Mamedov, İ.G.

doi:10.1107/S2056989022004297

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ISSN: 2056-9890

Volume 78| Part 5| May 2022| Pages 525-529

https://doi.org/10.1107/S2056989022004297

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Crystal structure and Hirshfeld surface analysis of 1-(tert-butylamino)-3-mesitylpropan-2-ol hemihydrate

Ali N. Khalilov,^a,^b Victor N. Khrustalev,^c,^d Tatiana A. Tereshina,^c Mehmet Akkurt,^e Rovnag M. Rzayev,^a Anzurat A. Akobirshoeva ^f ^* and İbrahim G. Mamedov ^b

^a"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, ^bDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az 1148, Baku, Azerbaijan, ^cPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, ^dN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, ^eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^fAcad. Sci. Republ. Tadzhikistan, Kh. Yu. Yusufbekov Pamir Biol Inst, 1 Kholdorova St, Khorog 736002, Gbao, Tajikistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by J. Reibenspies, Texas A & M University, USA (Received 21 March 2022; accepted 21 April 2022; online 28 April 2022)

The title compound, 2C₁₆H₂₇NO·H₂O, crystallizes in the monoclinic P2₁/c space group with two independent molecules (A and B) in the asymmetric unit. In the crystal, molecules A and B are linked through the water molecules by intermolecular O—H⋯O and O—H⋯N hydrogen bonds, producing chains along the b-axis direction. These chains are linked with neighboring chains parallel to the (103) plane via C—H⋯π interactions, generating ribbons along the b-axis direction. The stability of the molecular packaging is ensured by van der Waals interactions between the ribbons. According to the Hirshfeld surface study, H⋯H interactions are the most significant contributors to the crystal packing (80.3% for molecule A and 84.8% for molecule B).

Keywords: crystal structure; 1,2-amino alcohols; hydrogen bonds; C—H⋯π interactions; Hirshfeld surface analysis.

CCDC reference: 2168161

1. Chemical context

Amine group-containing compounds are of great interest in the fields of organic synthesis, catalysis, material science and medicinal chemistry (Zubkov et al., 2018 ; Shikhaliyev et al., 2019 ; Viswanathan et al., 2019 ; Gurbanov et al., 2020 ). In particular, the β-amino alcohol moiety is the predominant structural motif in a series of natural and synthetic biologically active molecules (Lee & Kang, 2004 ). Amino alcohol derivatives are currently being studied for their antimicrobial, antifungal, antioxidant, cytotoxic, enzyme inhibitory and other important biological activities, which have been well documented in recent works (Baker et al., 2021 ; Estolano-Cobián et al., 2020 ; Tafelska-Kaczmarek et al., 2020 ).

In this study, in the framework of ongoing structural studies (Safavora et al., 2019 ; Aliyeva et al., 2011 ; Mamedov et al., 2022 ), we report the crystal structure and Hirshfeld surface analysis of the title compound, 1-(tert-butylamino)-3-mesitylpropan-2-ol hemihydrate.

2. Structural commentary

The title compound (Fig. 1) contains the two independent molecules (molecule A containing atom N1 and molecule B containing N2) in the asymmetric unit. As shown in Fig. 2 (r.m.s. deviation = 0.006 Å), while the 1,2,3,5-tetramethylbenzene parts of molecules A and B are overlapped, their 2-(tert-butylamino)ethan-1-ol moieties do not overlap, but rather are oriented in opposite directions. Atoms C2 in molecule A and C18 in molecule B have opposite chiralities. The chirality about the C2 atom is R and that about C18, S. The values of the geometric parameters of molecules A and B are normal and compatible with those of the related compounds mentioned in the Database survey section.

Figure 1
View of the two independent molecules, A and B, in the asymmetric unit of the title compound, with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. For clarity, the minor components of disorder in molecule B are omitted.

Figure 2
Overlay image of the two independent molecules (A and B) in the asymmetric unit of the title compound. Both the major and minor components of disorder in molecule B are shown. Color code: carbon (gray), hydrogen (white), nitrogen (blue) and oxygen (red).

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules A and B are linked through the water molecules by intermolecular O—H⋯O and O—H⋯N hydrogen bonds (Table 1; Figs. 3 and 4), forming chains along the b-axis direction. These chains are linked by C—H⋯π interactions with neighboring chains parallel to the (103) plane, forming ribbons along the b-axis direction (Table 1; Figs. 5 and 6). The stability of the molecular packing is ensured by van der Waals interactions between the ribbons.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the benzene ring (C4–C9) of molecule A.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3	0.91 (2)	1.82 (2)	2.725 (5)	173 (2)
O1—H1O⋯O3′	0.91 (2)	1.82 (2)	2.697 (6)	161 (2)
O2—H2O⋯N1	0.91 (2)	1.83 (2)	2.7273 (13)	168.0 (19)
O3—H3C⋯O2ⁱ	0.95 (2)	1.83 (2)	2.753 (3)	162 (2)
O3′—H3C⋯O2ⁱ	0.92 (2)	1.83 (2)	2.685 (4)	153 (2)
O3—H3D⋯N2	0.98 (3)	1.87 (3)	2.827 (3)	164 (2)
O3′—H3D⋯N2	1.07 (3)	1.87 (3)	2.875 (5)	155 (2)
C11—H11B⋯Cg2ⁱⁱ	0.98	2.90	3.7613 (17)	147
Symmetry codes: (i) ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 3
A view of the intermolecular O—H⋯O and O—H⋯N interactions along the a axis in the crystal structure of the title compound. For clarity, H atoms not involved in hydrogen bonding and the minor disorder components in molecule B are omitted.

Figure 4
A view of the intermolecular O—H⋯O and O—H⋯N interactions along the b axis in the crystal structure of the title compound. For clarity, H atoms not involved in hydrogen bonding and the minor disorder components in molecule B are omitted.

Figure 5
A view of the intermolecular O—H⋯O and O—H⋯N interactions and C—H⋯π interactions along the a axis in the crystal structure of the title compound. For clarity, H atoms not involved in hydrogen bonding and the minor disorder components in molecule B are omitted.

Figure 6
A view of the intermolecular O—H⋯O and O—H⋯N interactions and C—H⋯π interactions along the b axis in the crystal structure of the title compound. For clarity, H atoms not involved in hydrogen bonding and the minor disorder components in molecule B are omitted.

Hirshfeld surfaces were generated for both independent molecules using Crystal Explorer 17 (Turner et al., 2017 ). The d_norm mappings for molecules A and B were performed in the ranges −0.6784 to 1.2952 a.u. and −0.6765 to 1.3828 a.u., respectively. The O—H⋯O and O—H⋯N interactions are indicated by red areas on the Hirshfeld surfaces (Fig. 7a,b for A and Fig. 7c,d for B).

Figure 7
Front (a) and back (b) views of the three-dimensional Hirshfeld surface for molecule A. Front (c) and back (d) views of the three-dimensional Hirshfeld surface for molecule B. Some intermolecular O—H⋯O and O—H⋯N interactions are shown.

Fingerprint plots (Fig. 8) reveal that while H⋯H interactions (80.3% for molecule A and 84.8% for molecule B) make the largest contributions to surface contacts (Tables 1 and 2), C⋯H/H⋯C contacts (13.0% for molecule A and 9.1% for molecule B) are also important. Other, less notable linkages are O⋯H/H⋯O (5.7% contribution for molecule A and 4.3% for molecule B) and N⋯H/H⋯N (1.0% for molecule A and 1.8% for molecule B). The surroundings of molecules A and B are very similar, as can be observed from the comparison of the supplied data.

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
O2⋯H3C	1.83	x, 1 + y, z
H2O⋯N1	1.83	x, y, z
N2⋯H3D	1.87	x, y, z
H26C⋯H15B	2.58	1 − x, 2 − y, 1 − z
*H31D⋯H17B	2.34	x, − 1 + y, z
H32B⋯H30E	2.50	1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H24⋯H3B	2.39	−1 + x, y, z
H26B⋯H15C	2.58	1 − x, 1 − y, 1 − z
*H30C⋯C10	3.00	x, −1 + y, z
*H31B⋯H6	2.44	1 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
*H32D⋯H11C	2.48	1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H1O⋯*O3′	1.82	x, y, z
H1O⋯H1B	2.46	x, −1 + y, z
C9⋯H11B	2.84	2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H16C⋯*O3′	2.89	x, 1 + y, z
The prefix * denotes atoms of the disordered parts of the molecules.

Figure 8
The two-dimensional fingerprint plots for molecules A and B of the title compound showing (a) all interactions, and delineated into (b) H⋯H and (c) C⋯H/H⋯C interactions. The d_ĩ and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

Two related compounds were found in a search of the Cambridge Structural Database (CSD, version 5.42, update of September 2021; Groom et al., 2016 ), viz. 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol (ULIMUY; Maharramov et al., 2011a ) and 3-[2-hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea (URAPOT; Maharramov et al., 2011b ).

In ULIMUY, the methylaminopropyl chain adopts an extended zigzag conformation and the N atom shows a trigonal coordination. The N atom acts as hydrogen-bond acceptor to the hydroxy group of an adjacent molecule to generate a helical chain running along the b-axis of the monoclinic unit cell.

In URAPOT, the four-atoms N—C(=S)—N unit is planar (r.m.s. deviation of 0.005 Å); the phenyl ring connected to one of the two flanking N atoms is twisted out of this plane by 28.6 (1)°. The propyl chain connected to the other N atom bears a hydroxy substituent; this serves as hydrogen-bond donor and acceptor to the double-bonded S atom of an inversion-related molecule, generating a hydrogen-bonded dimer.

5. Synthesis and crystallization

The title compound was synthesized using our previously reported procedure (Khalilov et al., 2021 ), and colorless crystals were obtained upon recrystallization from an ethanol solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. Carbon-bound H atoms were placed in calculated positions [C—H = 0.95 to 1.00 Å; U_iso(H) = 1.2 or 1.5U_eq(C)] and were included in the refinement in the riding-model approximation. The hydroxy and amino H atoms were located in a difference Fourier map, and were freely refined [O1—H1O = 0.91 (2) Å, O2—H2O = 0.91 (2) Å, N1—H1N = 0.922 (16) Å and N2—H2N = 0.922 (18) Å]. In molecule B, the methyl groups of the 2-methylpropane moiety are disordered over two sets of sites with an occupancy ratio of 0.65 (3):0.35 (3). The water molecule is disordered over two positions with an occupancy ratio of 0.59 (3):0.41 (3). The two H atoms of the water molecule were found in a difference-Fourier map and freely refined [O3—H3C = 0.95 (2) Å, O3—H3D = 0.98 (3) Å, O3′—H3C = 0.92 (2) Å and O3′—H3D = 1.07 (3) Å]. The anisotropic displacement parameters of the O3 and O3′ atoms of the disordered water molecule were restrained to be equal (SIMU). SADI and DFIX commands were used for the treatment of the disordered methyl groups of the 2-methylpropane moiety of molecule B.

Table 3
Experimental details

Crystal data
Chemical formula	2C₁₆H₂₇NO·H₂O
M_r	516.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.06508 (16), 5.81242 (6), 41.7384 (5)
β (°)	93.3315 (11)
V (Å³)	3164.25 (6)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.53
Crystal size (mm)	0.36 × 0.12 × 0.06

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ )
T_min, T_max	0.805, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	40427, 6866, 6251
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.09
No. of reflections	6866
No. of parameters	411
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2168161

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022004297/jy2019sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022004297/jy2019Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989022004297/jy2019Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

1-(tert-Butylamino)-3-(2,4,6-trimethylphenyl)propan-2-ol hemihydrate top

Crystal data top

2C₁₆H₂₇NO·H₂O	F(000) = 1144
M_r = 516.79	D_x = 1.085 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.06508 (16) Å	Cell parameters from 22446 reflections
b = 5.81242 (6) Å	θ = 2.2–79.1°
c = 41.7384 (5) Å	µ = 0.53 mm⁻¹
β = 93.3315 (11)°	T = 100 K
V = 3164.25 (6) Å³	Plate, colourless
Z = 4	0.36 × 0.12 × 0.06 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	6251 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.041
φ and ω scans	θ_max = 79.7°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −16→16
T_min = 0.805, T_max = 0.941	k = −6→7
40427 measured reflections	l = −53→52
6866 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: mixed
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0467P)² + 0.9632P] where P = (F_o² + 2F_c²)/3
6866 reflections	(Δ/σ)_max = 0.001
411 parameters	Δρ_max = 0.19 e Å⁻³
21 restraints	Δρ_min = −0.20 e Å⁻³

Special details top

Experimental. CrysAlisPro 1.171.41.117a (Rigaku OD, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	Occ. (<1)
O1	0.83664 (7)	0.63481 (14)	0.38179 (2)	0.02938 (18)
H1O	0.7755 (17)	0.562 (4)	0.3786 (5)	0.068 (6)*
N1	0.75396 (7)	0.93228 (16)	0.42788 (2)	0.02387 (19)
H1N	0.7600 (11)	0.774 (3)	0.4290 (3)	0.031 (4)*
C1	0.82855 (8)	1.01229 (19)	0.40524 (3)	0.0256 (2)
H1A	0.8989	0.9969	0.4152	0.031*
H1B	0.8163	1.1769	0.4003	0.031*
C2	0.81900 (8)	0.87226 (18)	0.37442 (3)	0.0252 (2)
H2	0.7481	0.8905	0.3644	0.030*
C3	0.89639 (9)	0.9587 (2)	0.35095 (3)	0.0293 (2)
H3A	0.8870	1.1266	0.3481	0.035*
H3B	0.9665	0.9334	0.3606	0.035*
C4	0.88794 (9)	0.8449 (2)	0.31835 (3)	0.0291 (2)
C5	0.81775 (9)	0.9285 (2)	0.29442 (3)	0.0325 (3)
C6	0.81180 (9)	0.8239 (2)	0.26423 (3)	0.0360 (3)
H6	0.7642	0.8817	0.2481	0.043*
C7	0.87307 (10)	0.6384 (2)	0.25699 (3)	0.0363 (3)
C8	0.94234 (10)	0.5581 (2)	0.28094 (3)	0.0359 (3)
H8	0.9851	0.4314	0.2764	0.043*
C9	0.95115 (9)	0.6570 (2)	0.31138 (3)	0.0322 (3)
C10	0.74982 (11)	1.1329 (2)	0.30008 (3)	0.0393 (3)
H10A	0.7097	1.1034	0.3188	0.059*
H10B	0.7033	1.1580	0.2811	0.059*
H10C	0.7924	1.2700	0.3040	0.059*
C11	0.86603 (12)	0.5272 (3)	0.22430 (3)	0.0462 (3)
H11A	0.8362	0.3732	0.2259	0.069*
H11B	0.9348	0.5150	0.2162	0.069*
H11C	0.8225	0.6210	0.2095	0.069*
C12	1.03108 (10)	0.5649 (3)	0.33569 (3)	0.0400 (3)
H12A	1.0620	0.4256	0.3272	0.060*
H12B	0.9987	0.5279	0.3557	0.060*
H12C	1.0843	0.6814	0.3400	0.060*
C13	0.76617 (8)	1.02608 (19)	0.46103 (3)	0.0247 (2)
C14	0.86787 (9)	0.9562 (2)	0.47850 (3)	0.0336 (3)
H14A	0.8726	0.7880	0.4794	0.050*
H14B	0.8710	1.0182	0.5004	0.050*
H14C	0.9250	1.0176	0.4669	0.050*
C15	0.67782 (9)	0.9273 (2)	0.47916 (3)	0.0288 (2)
H15A	0.6125	0.9847	0.4695	0.043*
H15B	0.6853	0.9748	0.5017	0.043*
H15C	0.6790	0.7589	0.4779	0.043*
C16	0.75688 (10)	1.2882 (2)	0.45967 (3)	0.0306 (2)
H16A	0.8151	1.3522	0.4488	0.046*
H16B	0.7568	1.3497	0.4815	0.046*
H16C	0.6928	1.3306	0.4478	0.046*
O2	0.57184 (6)	1.06462 (16)	0.39828 (2)	0.0352 (2)
H2O	0.6278 (15)	1.004 (3)	0.4093 (5)	0.062 (5)*
N2	0.50806 (8)	0.78162 (18)	0.34494 (2)	0.0306 (2)
H2N	0.5598 (13)	0.887 (3)	0.3424 (4)	0.047 (4)*
C17	0.43655 (8)	0.8875 (2)	0.36627 (3)	0.0283 (2)
H17A	0.3746	0.7901	0.3671	0.034*
H17B	0.4151	1.0399	0.3577	0.034*
C18	0.48579 (8)	0.91565 (19)	0.39983 (3)	0.0264 (2)
H18	0.5096	0.7620	0.4081	0.032*
C19	0.41002 (9)	1.01744 (19)	0.42282 (3)	0.0271 (2)
H19A	0.4465	1.0414	0.4440	0.032*
H19B	0.3876	1.1702	0.4146	0.032*
C20	0.31558 (8)	0.87209 (19)	0.42747 (2)	0.0244 (2)
C21	0.32295 (8)	0.67813 (19)	0.44783 (2)	0.0246 (2)
C22	0.23623 (9)	0.5454 (2)	0.45241 (3)	0.0269 (2)
H22	0.2424	0.4139	0.4659	0.032*
C23	0.14096 (9)	0.5996 (2)	0.43785 (3)	0.0286 (2)
C24	0.13486 (8)	0.7904 (2)	0.41774 (3)	0.0287 (2)
H24	0.0704	0.8298	0.4075	0.034*
C25	0.21998 (9)	0.92618 (19)	0.41200 (3)	0.0264 (2)
C26	0.42242 (9)	0.6101 (2)	0.46563 (3)	0.0288 (2)
H26A	0.4727	0.5667	0.4502	0.043*
H26B	0.4103	0.4793	0.4797	0.043*
H26C	0.4488	0.7403	0.4785	0.043*
C27	0.04768 (9)	0.4554 (2)	0.44353 (3)	0.0369 (3)
H27A	0.0240	0.4888	0.4649	0.055*
H27B	0.0654	0.2920	0.4422	0.055*
H27C	−0.0070	0.4917	0.4272	0.055*
C28	0.20503 (9)	1.1238 (2)	0.38851 (3)	0.0317 (2)
H28A	0.2394	1.2613	0.3974	0.047*
H28B	0.1316	1.1549	0.3847	0.047*
H28C	0.2344	1.0828	0.3682	0.047*
C29	0.46433 (9)	0.7090 (2)	0.31290 (3)	0.0363 (3)
C30	0.5508 (4)	0.5955 (11)	0.29559 (17)	0.074 (2)	0.65 (3)
H30A	0.6091	0.7013	0.2952	0.111*	0.65 (3)
H30B	0.5266	0.5583	0.2735	0.111*	0.65 (3)
H30C	0.5722	0.4540	0.3069	0.111*	0.65 (3)
C31	0.3778 (4)	0.5356 (8)	0.31656 (15)	0.0441 (12)	0.65 (3)
H31A	0.3992	0.4212	0.3329	0.066*	0.65 (3)
H31B	0.3621	0.4583	0.2960	0.066*	0.65 (3)
H31C	0.3166	0.6162	0.3232	0.066*	0.65 (3)
C32	0.4236 (5)	0.9172 (8)	0.29385 (14)	0.0441 (12)	0.65 (3)
H32A	0.3700	0.9927	0.3055	0.066*	0.65 (3)
H32B	0.3950	0.8668	0.2728	0.066*	0.65 (3)
H32C	0.4797	1.0258	0.2910	0.066*	0.65 (3)
C30'	0.5561 (7)	0.632 (3)	0.2945 (2)	0.071 (4)	0.35 (3)
H30D	0.5967	0.7664	0.2891	0.107*	0.35 (3)
H30E	0.5317	0.5529	0.2748	0.107*	0.35 (3)
H30F	0.5987	0.5265	0.3079	0.107*	0.35 (3)
C31'	0.3957 (13)	0.503 (2)	0.3189 (3)	0.088 (5)	0.35 (3)
H31D	0.4373	0.3773	0.3285	0.132*	0.35 (3)
H31E	0.3625	0.4508	0.2985	0.132*	0.35 (3)
H31F	0.3432	0.5472	0.3336	0.132*	0.35 (3)
C32'	0.4036 (12)	0.891 (2)	0.2936 (3)	0.044 (2)	0.35 (3)
H32D	0.3457	0.9426	0.3057	0.066*	0.35 (3)
H32E	0.3779	0.8259	0.2731	0.066*	0.35 (3)
H32F	0.4482	1.0228	0.2897	0.066*	0.35 (3)
O3	0.6489 (2)	0.4428 (10)	0.3681 (3)	0.0388 (14)	0.59 (3)
O3'	0.6420 (5)	0.4819 (13)	0.3828 (5)	0.044 (3)	0.41 (3)
H3C	0.6156 (16)	0.335 (4)	0.3812 (5)	0.072 (6)*
H3D	0.5940 (18)	0.556 (4)	0.3639 (6)	0.083 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0295 (4)	0.0246 (4)	0.0344 (4)	0.0009 (3)	0.0046 (3)	0.0014 (3)
N1	0.0240 (4)	0.0230 (4)	0.0249 (4)	−0.0032 (3)	0.0039 (3)	−0.0005 (3)
C1	0.0234 (5)	0.0268 (5)	0.0270 (5)	−0.0030 (4)	0.0039 (4)	0.0010 (4)
C2	0.0232 (5)	0.0250 (5)	0.0277 (5)	0.0005 (4)	0.0038 (4)	0.0019 (4)
C3	0.0270 (5)	0.0315 (6)	0.0300 (6)	−0.0026 (4)	0.0063 (4)	0.0010 (5)
C4	0.0259 (5)	0.0331 (6)	0.0290 (5)	−0.0024 (4)	0.0086 (4)	0.0021 (4)
C5	0.0287 (6)	0.0386 (6)	0.0312 (6)	0.0008 (5)	0.0095 (4)	0.0042 (5)
C6	0.0307 (6)	0.0487 (7)	0.0291 (6)	0.0007 (5)	0.0058 (5)	0.0030 (5)
C7	0.0313 (6)	0.0458 (7)	0.0327 (6)	−0.0048 (5)	0.0099 (5)	−0.0035 (5)
C8	0.0301 (6)	0.0398 (7)	0.0388 (6)	0.0019 (5)	0.0105 (5)	−0.0044 (5)
C9	0.0257 (5)	0.0375 (6)	0.0342 (6)	0.0003 (5)	0.0081 (4)	0.0004 (5)
C10	0.0409 (7)	0.0437 (7)	0.0341 (6)	0.0098 (6)	0.0088 (5)	0.0077 (5)
C11	0.0438 (7)	0.0593 (9)	0.0363 (7)	−0.0035 (7)	0.0082 (6)	−0.0105 (6)
C12	0.0322 (6)	0.0471 (7)	0.0408 (7)	0.0089 (5)	0.0036 (5)	−0.0019 (6)
C13	0.0251 (5)	0.0251 (5)	0.0240 (5)	−0.0023 (4)	0.0009 (4)	0.0000 (4)
C14	0.0292 (6)	0.0405 (6)	0.0305 (6)	−0.0014 (5)	−0.0024 (4)	0.0030 (5)
C15	0.0311 (6)	0.0297 (5)	0.0260 (5)	−0.0032 (4)	0.0046 (4)	0.0002 (4)
C16	0.0377 (6)	0.0258 (5)	0.0285 (5)	−0.0035 (5)	0.0028 (5)	−0.0026 (4)
O2	0.0249 (4)	0.0390 (5)	0.0412 (5)	−0.0096 (3)	−0.0023 (3)	0.0157 (4)
N2	0.0274 (5)	0.0342 (5)	0.0307 (5)	0.0032 (4)	0.0048 (4)	0.0018 (4)
C17	0.0247 (5)	0.0339 (6)	0.0266 (5)	0.0012 (4)	0.0028 (4)	0.0027 (4)
C18	0.0229 (5)	0.0273 (5)	0.0288 (5)	−0.0046 (4)	0.0006 (4)	0.0058 (4)
C19	0.0286 (5)	0.0265 (5)	0.0258 (5)	−0.0043 (4)	−0.0010 (4)	0.0008 (4)
C20	0.0252 (5)	0.0267 (5)	0.0215 (5)	−0.0001 (4)	0.0027 (4)	−0.0021 (4)
C21	0.0240 (5)	0.0284 (5)	0.0215 (5)	−0.0006 (4)	0.0025 (4)	−0.0016 (4)
C22	0.0275 (5)	0.0298 (5)	0.0236 (5)	−0.0016 (4)	0.0037 (4)	0.0012 (4)
C23	0.0240 (5)	0.0356 (6)	0.0266 (5)	−0.0022 (4)	0.0045 (4)	−0.0027 (4)
C24	0.0221 (5)	0.0373 (6)	0.0268 (5)	0.0034 (4)	0.0013 (4)	−0.0024 (5)
C25	0.0279 (5)	0.0288 (5)	0.0227 (5)	0.0029 (4)	0.0024 (4)	−0.0023 (4)
C26	0.0263 (5)	0.0319 (6)	0.0278 (5)	−0.0016 (4)	−0.0005 (4)	0.0050 (4)
C27	0.0267 (6)	0.0455 (7)	0.0389 (6)	−0.0052 (5)	0.0048 (5)	0.0025 (5)
C28	0.0305 (6)	0.0341 (6)	0.0303 (6)	0.0058 (5)	0.0007 (4)	0.0033 (5)
C29	0.0402 (7)	0.0371 (6)	0.0319 (6)	0.0003 (5)	0.0058 (5)	−0.0048 (5)
C30	0.049 (3)	0.105 (4)	0.071 (4)	0.004 (3)	0.024 (3)	−0.038 (3)
C31	0.055 (2)	0.0376 (16)	0.0394 (19)	−0.0078 (15)	0.0027 (13)	−0.0046 (13)
C32	0.055 (2)	0.052 (2)	0.0242 (16)	−0.0116 (16)	−0.0053 (14)	0.0028 (14)
C30'	0.087 (8)	0.087 (6)	0.038 (5)	0.049 (5)	−0.008 (4)	−0.029 (4)
C31'	0.147 (11)	0.053 (5)	0.060 (5)	−0.052 (6)	−0.023 (7)	−0.003 (4)
C32'	0.044 (4)	0.044 (3)	0.041 (4)	−0.004 (3)	−0.012 (3)	−0.005 (3)
O3	0.0282 (9)	0.0331 (13)	0.055 (3)	−0.0023 (7)	0.0027 (11)	0.0153 (17)
O3'	0.0310 (15)	0.0302 (17)	0.068 (7)	−0.0053 (12)	−0.011 (2)	0.016 (3)

Geometric parameters (Å, º) top

O1—C2	1.4298 (13)	C18—C19	1.5367 (16)
O1—H1O	0.91 (2)	C18—H18	1.0000
N1—C1	1.4718 (13)	C19—C20	1.5171 (15)
N1—C13	1.4872 (14)	C19—H19A	0.9900
N1—H1N	0.922 (16)	C19—H19B	0.9900
C1—C2	1.5211 (15)	C20—C25	1.4079 (15)
C1—H1A	0.9900	C20—C21	1.4118 (15)
C1—H1B	0.9900	C21—C22	1.3930 (15)
C2—C3	1.5330 (15)	C21—C26	1.5115 (15)
C2—H2	1.0000	C22—C23	1.3892 (16)
C3—C4	1.5117 (16)	C22—H22	0.9500
C3—H3A	0.9900	C23—C24	1.3899 (17)
C3—H3B	0.9900	C23—C27	1.5094 (16)
C4—C5	1.4030 (17)	C24—C25	1.3958 (16)
C4—C9	1.4096 (17)	C24—H24	0.9500
C5—C6	1.3972 (18)	C25—C28	1.5151 (16)
C5—C10	1.5097 (18)	C26—H26A	0.9800
C6—C7	1.3863 (19)	C26—H26B	0.9800
C6—H6	0.9500	C26—H26C	0.9800
C7—C8	1.3896 (19)	C27—H27A	0.9800
C7—C11	1.5081 (18)	C27—H27B	0.9800
C8—C9	1.3930 (18)	C27—H27C	0.9800
C8—H8	0.9500	C28—H28A	0.9800
C9—C12	1.5112 (18)	C28—H28B	0.9800
C10—H10A	0.9800	C28—H28C	0.9800
C10—H10B	0.9800	C29—C32'	1.525 (3)
C10—H10C	0.9800	C29—C30	1.526 (2)
C11—H11A	0.9800	C29—C31'	1.527 (3)
C11—H11B	0.9800	C29—C32	1.527 (2)
C11—H11C	0.9800	C29—C30'	1.528 (3)
C12—H12A	0.9800	C29—C31	1.529 (2)
C12—H12B	0.9800	C30—H30A	0.9800
C12—H12C	0.9800	C30—H30B	0.9800
C13—C15	1.5284 (15)	C30—H30C	0.9800
C13—C16	1.5289 (16)	C31—H31A	0.9800
C13—C14	1.5328 (15)	C31—H31B	0.9800
C14—H14A	0.9800	C31—H31C	0.9800
C14—H14B	0.9800	C32—H32A	0.9800
C14—H14C	0.9800	C32—H32B	0.9800
C15—H15A	0.9800	C32—H32C	0.9800
C15—H15B	0.9800	C30'—H30D	0.9800
C15—H15C	0.9800	C30'—H30E	0.9800
C16—H16A	0.9800	C30'—H30F	0.9800
C16—H16B	0.9800	C31'—H31D	0.9800
C16—H16C	0.9800	C31'—H31E	0.9800
O2—C18	1.4235 (13)	C31'—H31F	0.9800
O2—H2O	0.91 (2)	C32'—H32D	0.9800
N2—C17	1.4631 (15)	C32'—H32E	0.9800
N2—C29	1.4846 (16)	C32'—H32F	0.9800
N2—H2N	0.922 (18)	O3—H3C	0.95 (2)
C17—C18	1.5158 (16)	O3—H3D	0.98 (3)
C17—H17A	0.9900	O3'—H3C	0.92 (2)
C17—H17B	0.9900	O3'—H3D	1.07 (3)

C2—O1—H1O	106.9 (13)	O2—C18—H18	109.1
C1—N1—C13	116.25 (8)	C17—C18—H18	109.1
C1—N1—H1N	106.8 (9)	C19—C18—H18	109.1
C13—N1—H1N	108.2 (9)	C20—C19—C18	115.06 (9)
N1—C1—C2	110.42 (9)	C20—C19—H19A	108.5
N1—C1—H1A	109.6	C18—C19—H19A	108.5
C2—C1—H1A	109.6	C20—C19—H19B	108.5
N1—C1—H1B	109.6	C18—C19—H19B	108.5
C2—C1—H1B	109.6	H19A—C19—H19B	107.5
H1A—C1—H1B	108.1	C25—C20—C21	118.82 (10)
O1—C2—C1	109.29 (9)	C25—C20—C19	121.57 (10)
O1—C2—C3	110.48 (9)	C21—C20—C19	119.61 (10)
C1—C2—C3	109.88 (9)	C22—C21—C20	119.82 (10)
O1—C2—H2	109.1	C22—C21—C26	118.08 (10)
C1—C2—H2	109.1	C20—C21—C26	122.09 (10)
C3—C2—H2	109.1	C23—C22—C21	121.98 (11)
C4—C3—C2	114.54 (9)	C23—C22—H22	119.0
C4—C3—H3A	108.6	C21—C22—H22	119.0
C2—C3—H3A	108.6	C22—C23—C24	117.61 (10)
C4—C3—H3B	108.6	C22—C23—C27	121.08 (11)
C2—C3—H3B	108.6	C24—C23—C27	121.30 (11)
H3A—C3—H3B	107.6	C23—C24—C25	122.45 (10)
C5—C4—C9	119.21 (11)	C23—C24—H24	118.8
C5—C4—C3	119.98 (11)	C25—C24—H24	118.8
C9—C4—C3	120.79 (11)	C24—C25—C20	119.30 (10)
C6—C5—C4	119.40 (11)	C24—C25—C28	117.76 (10)
C6—C5—C10	118.77 (11)	C20—C25—C28	122.93 (10)
C4—C5—C10	121.81 (11)	C21—C26—H26A	109.5
C7—C6—C5	122.16 (12)	C21—C26—H26B	109.5
C7—C6—H6	118.9	H26A—C26—H26B	109.5
C5—C6—H6	118.9	C21—C26—H26C	109.5
C6—C7—C8	117.70 (12)	H26A—C26—H26C	109.5
C6—C7—C11	121.66 (12)	H26B—C26—H26C	109.5
C8—C7—C11	120.64 (12)	C23—C27—H27A	109.5
C7—C8—C9	122.21 (12)	C23—C27—H27B	109.5
C7—C8—H8	118.9	H27A—C27—H27B	109.5
C9—C8—H8	118.9	C23—C27—H27C	109.5
C8—C9—C4	119.31 (11)	H27A—C27—H27C	109.5
C8—C9—C12	118.91 (11)	H27B—C27—H27C	109.5
C4—C9—C12	121.74 (11)	C25—C28—H28A	109.5
C5—C10—H10A	109.5	C25—C28—H28B	109.5
C5—C10—H10B	109.5	H28A—C28—H28B	109.5
H10A—C10—H10B	109.5	C25—C28—H28C	109.5
C5—C10—H10C	109.5	H28A—C28—H28C	109.5
H10A—C10—H10C	109.5	H28B—C28—H28C	109.5
H10B—C10—H10C	109.5	N2—C29—C32'	116.0 (6)
C7—C11—H11A	109.5	N2—C29—C30	107.0 (3)
C7—C11—H11B	109.5	N2—C29—C31'	106.0 (6)
H11A—C11—H11B	109.5	C32'—C29—C31'	109.9 (3)
C7—C11—H11C	109.5	N2—C29—C32	110.3 (3)
H11A—C11—H11C	109.5	C30—C29—C32	109.9 (2)
H11B—C11—H11C	109.5	N2—C29—C30'	105.3 (5)
C9—C12—H12A	109.5	C32'—C29—C30'	109.8 (3)
C9—C12—H12B	109.5	C31'—C29—C30'	109.7 (3)
H12A—C12—H12B	109.5	N2—C29—C31	110.2 (3)
C9—C12—H12C	109.5	C30—C29—C31	109.6 (2)
H12A—C12—H12C	109.5	C32—C29—C31	109.7 (2)
H12B—C12—H12C	109.5	C29—C30—H30A	109.5
N1—C13—C15	106.23 (8)	C29—C30—H30B	109.5
N1—C13—C16	109.07 (9)	H30A—C30—H30B	109.5
C15—C13—C16	109.40 (9)	C29—C30—H30C	109.5
N1—C13—C14	112.86 (9)	H30A—C30—H30C	109.5
C15—C13—C14	108.89 (9)	H30B—C30—H30C	109.5
C16—C13—C14	110.27 (10)	C29—C31—H31A	109.5
C13—C14—H14A	109.5	C29—C31—H31B	109.5
C13—C14—H14B	109.5	H31A—C31—H31B	109.5
H14A—C14—H14B	109.5	C29—C31—H31C	109.5
C13—C14—H14C	109.5	H31A—C31—H31C	109.5
H14A—C14—H14C	109.5	H31B—C31—H31C	109.5
H14B—C14—H14C	109.5	C29—C32—H32A	109.5
C13—C15—H15A	109.5	C29—C32—H32B	109.5
C13—C15—H15B	109.5	H32A—C32—H32B	109.5
H15A—C15—H15B	109.5	C29—C32—H32C	109.5
C13—C15—H15C	109.5	H32A—C32—H32C	109.5
H15A—C15—H15C	109.5	H32B—C32—H32C	109.5
H15B—C15—H15C	109.5	C29—C30'—H30D	109.5
C13—C16—H16A	109.5	C29—C30'—H30E	109.5
C13—C16—H16B	109.5	H30D—C30'—H30E	109.5
H16A—C16—H16B	109.5	C29—C30'—H30F	109.5
C13—C16—H16C	109.5	H30D—C30'—H30F	109.5
H16A—C16—H16C	109.5	H30E—C30'—H30F	109.5
H16B—C16—H16C	109.5	C29—C31'—H31D	109.5
C18—O2—H2O	110.6 (13)	C29—C31'—H31E	109.5
C17—N2—C29	116.22 (9)	H31D—C31'—H31E	109.5
C17—N2—H2N	106.8 (11)	C29—C31'—H31F	109.5
C29—N2—H2N	109.4 (11)	H31D—C31'—H31F	109.5
N2—C17—C18	110.86 (9)	H31E—C31'—H31F	109.5
N2—C17—H17A	109.5	C29—C32'—H32D	109.5
C18—C17—H17A	109.5	C29—C32'—H32E	109.5
N2—C17—H17B	109.5	H32D—C32'—H32E	109.5
C18—C17—H17B	109.5	C29—C32'—H32F	109.5
H17A—C17—H17B	108.1	H32D—C32'—H32F	109.5
O2—C18—C17	108.52 (9)	H32E—C32'—H32F	109.5
O2—C18—C19	109.47 (9)	H3C—O3—H3D	100.9 (19)
C17—C18—C19	111.38 (9)	H3C—O3'—H3D	97 (2)

C13—N1—C1—C2	169.98 (9)	N2—C17—C18—C19	−177.64 (9)
N1—C1—C2—O1	−59.13 (11)	O2—C18—C19—C20	−178.38 (9)
N1—C1—C2—C3	179.49 (9)	C17—C18—C19—C20	61.61 (12)
O1—C2—C3—C4	64.12 (12)	C18—C19—C20—C25	−102.29 (12)
C1—C2—C3—C4	−175.21 (10)	C18—C19—C20—C21	77.93 (13)
C2—C3—C4—C5	85.11 (13)	C25—C20—C21—C22	−0.39 (16)
C2—C3—C4—C9	−95.98 (13)	C19—C20—C21—C22	179.39 (10)
C9—C4—C5—C6	0.10 (17)	C25—C20—C21—C26	−179.24 (10)
C3—C4—C5—C6	179.03 (11)	C19—C20—C21—C26	0.55 (16)
C9—C4—C5—C10	−178.41 (11)	C20—C21—C22—C23	−1.02 (17)
C3—C4—C5—C10	0.52 (17)	C26—C21—C22—C23	177.87 (10)
C4—C5—C6—C7	0.16 (19)	C21—C22—C23—C24	1.29 (17)
C10—C5—C6—C7	178.71 (12)	C21—C22—C23—C27	−179.10 (11)
C5—C6—C7—C8	−0.30 (19)	C22—C23—C24—C25	−0.17 (17)
C5—C6—C7—C11	−179.92 (12)	C27—C23—C24—C25	−179.78 (11)
C6—C7—C8—C9	0.20 (19)	C23—C24—C25—C20	−1.20 (17)
C11—C7—C8—C9	179.81 (12)	C23—C24—C25—C28	177.42 (11)
C7—C8—C9—C4	0.05 (19)	C21—C20—C25—C24	1.46 (16)
C7—C8—C9—C12	−177.80 (12)	C19—C20—C25—C24	−178.32 (10)
C5—C4—C9—C8	−0.20 (17)	C21—C20—C25—C28	−177.09 (10)
C3—C4—C9—C8	−179.12 (11)	C19—C20—C25—C28	3.13 (16)
C5—C4—C9—C12	177.59 (11)	C17—N2—C29—C32'	52.0 (7)
C3—C4—C9—C12	−1.33 (17)	C17—N2—C29—C30	−177.7 (3)
C1—N1—C13—C15	177.41 (9)	C17—N2—C29—C31'	−70.2 (8)
C1—N1—C13—C16	59.59 (12)	C17—N2—C29—C32	62.7 (3)
C1—N1—C13—C14	−63.33 (12)	C17—N2—C29—C30'	173.6 (6)
C29—N2—C17—C18	170.22 (10)	C17—N2—C29—C31	−58.6 (3)
N2—C17—C18—O2	61.79 (12)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the benzene ring (C4–C9) of molecule A.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3	0.91 (2)	1.82 (2)	2.725 (5)	173 (2)
O1—H1O···O3′	0.91 (2)	1.82 (2)	2.697 (6)	161 (2)
O2—H2O···N1	0.91 (2)	1.83 (2)	2.7273 (13)	168.0 (19)
O3—H3C···O2ⁱ	0.95 (2)	1.83 (2)	2.753 (3)	162 (2)
O3′—H3C···O2ⁱ	0.92 (2)	1.83 (2)	2.685 (4)	153 (2)
O3—H3D···N2	0.98 (3)	1.87 (3)	2.827 (3)	164 (2)
O3′—H3D···N2	1.07 (3)	1.87 (3)	2.875 (5)	155 (2)
C11—H11B···Cg2ⁱⁱ	0.98	2.90	3.7613 (17)	147

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

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
O2···H3C	1.83	x, 1 + y, z
H2O···N1	1.83	x, y, z
N2···H3D	1.87	x, y, z
H26C···H15B	2.58	1 - x, 2 - y, 1 - z
*H31D···H17B	2.34	x, - 1 + y, z
H32B···H30E	2.50	1 - x, 1/2 + y, 1/2 - z
H24···H3B	2.39	-1 + x, y, z
H26B···H15C	2.58	1 - x, 1 - y, 1 - z
*H30C···C10	3.00	x, -1 + y, z
*H31B···H6	2.44	1 - x, -1/2 + y, 1/2 - z
*H32D···H11C	2.48	1 - x, 1/2 + y, 1/2 - z
H1O···*O3'	1.82	x, y, z
H1O···H1B	2.46	x, -1 + y, z
C9···H11B	2.84	2 - x, 1/2 + y, 1/2 - z
H16C···*O3'	2.89	x, 1 + y, z

The prefix * denotes atoms of the disordered parts of the molecules.

Acknowledgements

Authors' contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK and IGM; investigation, ANK, MA and TAT; writing (original draft), MA and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, ANK and IGM; funding acquisition, VNK, RMR and ANK; resources, AAA, VNK and RMR; supervision, ANK and MA.

Funding information

This work was supported by Baku State University and the Ministry of Science and Higher Education of the Russian Federation [award No. 075–03–2020-223 (FSSF-2020–0017)].

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