Crystal structure and Hirshfeld surface analysis of 2,2′-(phenyl­aza­nedi­yl)bis­(1-phenyl­ethan-1-one)

Naghiyev, F.N.; Khrustalev, V.N.; Safronenko, M.G.; Akkurt, M.; Khalilov, A.N.; Bhattarai, A.; Mamedov, İ.G.

doi:10.1107/S2056989022005382

research communications

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ISSN: 2056-9890

Volume 78| Part 7| July 2022| Pages 691-694

https://doi.org/10.1107/S2056989022005382

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Crystal structure and Hirshfeld surface analysis of 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one)

Farid N. Naghiyev,^a Victor N. Khrustalev,^b,^c Marina G. Safronenko,^b Mehmet Akkurt,^d Ali N. Khalilov,^a,^e Ajaya Bhattarai ^f ^* and İbrahim G. Mamedov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, Azerbaijan, ^bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198, Russian Federation, ^cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^e"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, and ^fDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 16 May 2022; accepted 20 May 2022; online 7 June 2022)

The whole molecule of the title compound, C₂₂H₁₉NO₂, is generated by twofold rotational symmetry. The N atom exhibits a trigonal-planar geometry and is located on the twofold rotation axis. In the crystal, molecules are linked by C—H⋯O contacts with R²₂(12) ring motifs, and C—H⋯π interactions, resulting in ribbons along the c-axis direction. van der Waals interactions between these ribbons consolidate the molecular packing. Hirshfeld surface analysis indicates that the greatest contributions to the crystal packing are from H⋯H (45.5%), C⋯H/H⋯C (38.2%) and O⋯H/H⋯O (16.0%) interactions.

Keywords: crystal structure; C—H⋯O hydrogen bonds; C—H⋯··π interactions; van der Waals interactions; Hirshfeld surface.

CCDC reference: 2173928

1. Chemical context

Functionalized amine and carbonyl compounds are versatile intermediates in organic synthesis, material science and medicinal chemistry (Zubkov et al., 2018 ; Shikhaliyev et al., 2019 ; Viswanathan et al., 2019 ; Gurbanov et al., 2020 ). N,N-bis(phenacyl)anilines are of particular significance in the fine chemical industry due to their use as precursors of various heterocyclic systems such as piperidine, triazepine, 1,4-dihydropyrazine, 1,4-oxazine, pyrrole and indoles (Zeng & Chen, 2006 ; Ravindran et al., 2007 ; Paul & Muthusubramanian, 2013 ; Yan et al., 2014 ).

Thus, in the framework of our ongoing structural studies (Naghiyev et al., 2020 , 2021 , 2022 ; Khalilov et al., 2022 ), we report the crystal structure and Hirshfeld surface analysis of the title compound, 2,2′-(phenylazanediyl)bis(1-phenylethan-1-one).

2. Structural commentary

The asymmetric unit of the title compound contains half a molecule, the complete molecule being generated by the twofold rotational axis. Atoms N1, C1 and C4 are located on the twofold rotation axis (Fig. 1). The N1 atom has a trigonal-planar geometry, and it is bonded to two C atoms (C5 and C5A) from two symmetry-related 1-phenylethan-1-one groups and atom C1 of the phenyl ring, which is divided by the twofold rotation axis. The phenyl ring (C1–C4/C2A/C3A) attached to the N1 atom and the phenyl rings (C7–C12 and C7A–C12A) of the two symmetry-related 1-phenylethan-1-one groups are oriented at 89.65 (6)° to each other.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules are linked by intermolecular C—H⋯O [C5—H5A⋯O1(x, −y + 1, z + $[{1\over 2}]$ ); 2.51 Å, 158°] interactions with $[R_{2}^{2}]$ (12) ring motifs, resulting in ribbons along the c-axis direction (Bernstein et al., 1995 ; Table 1; Fig. 2). C—H⋯π interactions also contribute to the stronger cohesion of molecules in the ribbons (Table 1; Fig. 3). The molecular packing also features van der Waals interactions between these ribbons.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl ring attached to atom N1.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.99	2.51	3.4483 (16)	158
C8—H8⋯Cg1ⁱⁱ	0.95	2.85	3.6963 (14)	148
C8—H8⋯Cg1ⁱⁱⁱ	0.95	2.85	3.6963 (14)	148
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Figure 2
A general view of the intermolecular C—H⋯O hydrogen bonds, and C—H⋯π interactions of the title compound. The hydrogen atoms not involved in the hydrogen bonds have been omitted for clarity. Symmetry codes: (a) x, y, z + 1; (b) 1 − x, y, $[{1\over 2}]$ − z; (c) x + $[{3\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1; (d) 1 − x, 1 − y, −z; (e) 1 − x, 1 − y, 1 − z; (f) x, 1 − y, − $[{1\over 2}]$ + z; (g) x, 1 − y, $[{1\over 2}]$ + z.

Figure 3
View of the packing down the c axis showing C—H⋯O hydrogen bonds and and C—H⋯π interactions in the title compound. The hydrogen atoms not involved in the hydrogen bonds have been omitted for clarity.

Crystal Explorer17.5 (Turner et al., 2017 ) was used to perform a Hirshfeld surface analysis and generate the associated two-dimensional fingerprint plots, with a standard resolution of the three-dimensional d_norm surfaces plotted over a fixed colour scale of −0.1305 (red) to 1.2546 (blue) a.u (Fig. 4). In the Hirshfeld surface mapped over d_norm (Fig. 4), the bright-red spots near atoms O1 and H5A indicate the short C—H⋯O contacts (Table 1). Other contacts are equal to or longer than the sum of van der Waals radii.

Figure 4
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm, with a fixed colour scale of −0.1305 to 1.2546 a.u. The C—H⋯O hydrogen bonds are shown.

Fingerprint plots (Fig. 5b–d; Table1) reveal that H⋯H (45.5%), C⋯H/H⋯C (38.2%) and O⋯H/H⋯O (16.0%) interactions make the greatest contributions to the surface contacts. N⋯H/H⋯N (0.3%) contacts also contribute to the overall crystal packing of the title compound. The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H, C⋯H/H⋯C and O⋯H/H⋯O interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

Figure 5
Two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O interactions. [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ) for the N,N-dimethylaniline moiety revealed three structures closely related to the title compound, viz. 4-methyl-N-[(4-methylphenyl)sulfonyl]-N-phenylbenzenesulfonamide [CSD refcode GOBNIW (I); Eren et al., 2014 ], N,N′-[(phenylimino)diethane-2,1-diyl]bis(pyridine-2-carboxamide) [IDIZOM (II); Li et al., 2013 ] and (2E,2′E)-dimethyl 2,2′-[(phenylazanediyl)bis(methylene)]bis(3-phenylacrylate) [XEBWUY (III); Sabari et al., 2012 ]. Like the title compound, the molecule of (I) possesses twofold rotational symmetry. The N atom has a trigonal-planar geometry and is located on the twofold rotation axis. Weak C—H⋯O hydrogen bonds connect the molecules, forming a three-dimensional network. The asymmetric unit of (II) contains two independent molecules with similar conformations. In the crystal, N—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into a three-dimensional supramolecular structure. Weak intermolecular C—H⋯π interactions are also observed. In (III), the C=C double bonds adopt an E configuration. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules into inversion dimers.

5. Synthesis and crystallization

The title compound was synthesized using the reported procedure (He et al., 2014 ), and pale-yellow needle-like crystals were obtained upon slow evaporation from an ethanol/water (4:1) homogeneous solution at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms bound to C atoms were positioned geometrically (C—H = 0.95 and 0.99 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(C). Owing to poor agreement between observed and calculated intensities, eighteen outliers (8 1 3, 1 5 6, 25 0 2, 4 5 3, 2 7 3, 1 2 3, 1 1 6, 7 3 0, 14 3 9, 5 3 0, 4 5 8, 0 4 0, 21 0 2, 7 4 8, 9 10 3, 2 4 0, 23 2 2, 2 8 5) were omitted during the final refinement cycle.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₉NO₂
M_r	329.38
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	20.8269 (2), 9.09843 (10), 9.0158 (1)
V (Å³)	1708.42 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.65
Crystal size (mm)	0.09 × 0.06 × 0.05

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.906, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	21247, 1834, 1746
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.637

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.142, 1.09
No. of reflections	1834
No. of parameters	115
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2173928

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005382/tx2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005382/tx2050Isup2.hkl

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: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2,2'-(Phenylazanediyl)bis(1-phenylethan-1-one) top

Crystal data top

C₂₂H₁₉NO₂	D_x = 1.281 Mg m⁻³
M_r = 329.38	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbcn	Cell parameters from 14002 reflections
a = 20.8269 (2) Å	θ = 4.3–79.0°
b = 9.09843 (10) Å	µ = 0.65 mm⁻¹
c = 9.0158 (1) Å	T = 100 K
V = 1708.42 (3) Å³	Prism, pale yellow
Z = 4	0.09 × 0.06 × 0.05 mm
F(000) = 696

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	1746 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.034
φ and ω scans	θ_max = 79.4°, θ_min = 4.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −26→26
T_min = 0.906, T_max = 0.939	k = −11→10
21247 measured reflections	l = −10→11
1834 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.142	w = 1/[σ²(F_o²) + (0.0811P)² + 0.6375P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1834 reflections	Δρ_max = 0.28 e Å⁻³
115 parameters	Δρ_min = −0.23 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
O1	0.38204 (5)	0.42787 (12)	0.14622 (11)	0.0346 (3)
N1	0.500000	0.50356 (17)	0.250000	0.0275 (4)
C1	0.500000	0.65552 (19)	0.250000	0.0258 (4)
C2	0.54585 (7)	0.73540 (15)	0.16825 (14)	0.0312 (3)
H2	0.577660	0.684521	0.112882	0.037*
C3	0.54488 (9)	0.88824 (18)	0.16798 (17)	0.0432 (4)
H3	0.575533	0.940593	0.110555	0.052*
C4	0.500000	0.9651 (2)	0.250000	0.0537 (7)
H4	0.499999	1.069489	0.250000	0.064*
C5	0.45804 (6)	0.41853 (14)	0.34384 (14)	0.0256 (3)
H5A	0.447899	0.476190	0.433961	0.031*
H5B	0.480651	0.328071	0.375413	0.031*
C6	0.39556 (6)	0.37610 (14)	0.26663 (14)	0.0262 (3)
C7	0.35248 (6)	0.26878 (14)	0.34230 (13)	0.0256 (3)
C8	0.36541 (6)	0.21454 (15)	0.48403 (15)	0.0304 (3)
H8	0.402012	0.248116	0.537005	0.036*
C9	0.32461 (7)	0.11135 (17)	0.54737 (16)	0.0362 (4)
H9	0.333629	0.073789	0.643461	0.043*
C10	0.27080 (7)	0.06284 (17)	0.47116 (17)	0.0362 (4)
H10	0.243425	−0.008843	0.514406	0.043*
C11	0.25697 (7)	0.11905 (17)	0.33172 (16)	0.0353 (4)
H11	0.219476	0.087802	0.280639	0.042*
C12	0.29775 (7)	0.22064 (15)	0.26696 (16)	0.0316 (3)
H12	0.288486	0.257788	0.170838	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0336 (5)	0.0400 (6)	0.0302 (5)	−0.0032 (4)	−0.0024 (4)	0.0071 (4)
N1	0.0260 (7)	0.0226 (7)	0.0338 (8)	0.000	0.0068 (6)	0.000
C1	0.0285 (8)	0.0239 (8)	0.0250 (8)	0.000	−0.0043 (6)	0.000
C2	0.0378 (8)	0.0281 (7)	0.0277 (7)	−0.0037 (5)	−0.0006 (5)	0.0014 (5)
C3	0.0632 (11)	0.0286 (7)	0.0378 (8)	−0.0102 (7)	0.0028 (7)	0.0047 (6)
C4	0.091 (2)	0.0228 (10)	0.0475 (13)	0.000	0.0033 (12)	0.000
C5	0.0251 (6)	0.0241 (6)	0.0277 (6)	−0.0004 (4)	0.0020 (4)	0.0007 (4)
C6	0.0266 (6)	0.0247 (6)	0.0272 (6)	0.0028 (5)	0.0027 (5)	−0.0019 (5)
C7	0.0254 (6)	0.0236 (6)	0.0277 (6)	0.0014 (5)	0.0035 (4)	−0.0028 (4)
C8	0.0292 (6)	0.0326 (7)	0.0292 (6)	−0.0036 (5)	0.0009 (5)	−0.0009 (5)
C9	0.0377 (7)	0.0407 (8)	0.0303 (7)	−0.0064 (6)	0.0040 (6)	0.0041 (6)
C10	0.0352 (7)	0.0367 (7)	0.0366 (7)	−0.0092 (6)	0.0086 (6)	−0.0019 (6)
C11	0.0305 (7)	0.0382 (8)	0.0372 (8)	−0.0086 (6)	0.0014 (5)	−0.0063 (6)
C12	0.0316 (7)	0.0328 (7)	0.0304 (7)	−0.0024 (5)	−0.0009 (5)	−0.0019 (5)

Geometric parameters (Å, º) top

O1—C6	1.2165 (16)	C5—H5B	0.9900
N1—C1	1.383 (2)	C6—C7	1.4913 (18)
N1—C5	1.4415 (14)	C7—C8	1.3960 (19)
N1—C5ⁱ	1.4416 (14)	C7—C12	1.3973 (19)
C1—C2ⁱ	1.4082 (16)	C8—C9	1.3892 (19)
C1—C2	1.4082 (16)	C8—H8	0.9500
C2—C3	1.391 (2)	C9—C10	1.387 (2)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.382 (2)	C10—C11	1.388 (2)
C3—H3	0.9500	C10—H10	0.9500
C4—H4	0.9500	C11—C12	1.384 (2)
C5—C6	1.5254 (17)	C11—H11	0.9500
C5—H5A	0.9900	C12—H12	0.9500

C1—N1—C5	122.46 (7)	O1—C6—C7	121.50 (12)
C1—N1—C5ⁱ	122.46 (7)	O1—C6—C5	120.45 (11)
C5—N1—C5ⁱ	115.08 (14)	C7—C6—C5	118.05 (11)
N1—C1—C2ⁱ	121.07 (9)	C8—C7—C12	119.44 (12)
N1—C1—C2	121.07 (9)	C8—C7—C6	122.28 (12)
C2ⁱ—C1—C2	117.86 (17)	C12—C7—C6	118.27 (12)
C3—C2—C1	120.47 (14)	C9—C8—C7	119.81 (13)
C3—C2—H2	119.8	C9—C8—H8	120.1
C1—C2—H2	119.8	C7—C8—H8	120.1
C4—C3—C2	120.98 (15)	C10—C9—C8	120.38 (13)
C4—C3—H3	119.5	C10—C9—H9	119.8
C2—C3—H3	119.5	C8—C9—H9	119.8
C3ⁱ—C4—C3	119.2 (2)	C9—C10—C11	119.97 (13)
C3ⁱ—C4—H4	120.4	C9—C10—H10	120.0
C3—C4—H4	120.4	C11—C10—H10	120.0
N1—C5—C6	112.65 (9)	C12—C11—C10	120.05 (13)
N1—C5—H5A	109.1	C12—C11—H11	120.0
C6—C5—H5A	109.1	C10—C11—H11	120.0
N1—C5—H5B	109.1	C11—C12—C7	120.32 (13)
C6—C5—H5B	109.1	C11—C12—H12	119.8
H5A—C5—H5B	107.8	C7—C12—H12	119.8

C5—N1—C1—C2ⁱ	−6.40 (9)	O1—C6—C7—C8	−176.33 (12)
C5ⁱ—N1—C1—C2ⁱ	173.60 (9)	C5—C6—C7—C8	4.37 (18)
C5—N1—C1—C2	173.59 (9)	O1—C6—C7—C12	4.30 (19)
C5ⁱ—N1—C1—C2	−6.41 (9)	C5—C6—C7—C12	−175.00 (11)
N1—C1—C2—C3	179.32 (10)	C12—C7—C8—C9	1.3 (2)
C2ⁱ—C1—C2—C3	−0.68 (10)	C6—C7—C8—C9	−178.06 (12)
C1—C2—C3—C4	1.4 (2)	C7—C8—C9—C10	−0.6 (2)
C2—C3—C4—C3ⁱ	−0.69 (11)	C8—C9—C10—C11	−0.9 (2)
C1—N1—C5—C6	93.41 (9)	C9—C10—C11—C12	1.7 (2)
C5ⁱ—N1—C5—C6	−86.59 (9)	C10—C11—C12—C7	−1.0 (2)
N1—C5—C6—O1	−8.70 (17)	C8—C7—C12—C11	−0.6 (2)
N1—C5—C6—C7	170.61 (11)	C6—C7—C12—C11	178.84 (12)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the phenyl ring attached to atom N1.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱⁱ	0.99	2.51	3.4483 (16)	158
C8—H8···Cg1ⁱⁱⁱ	0.95	2.85	3.6963 (14)	148
C8—H8···Cg1^iv	0.95	2.85	3.6963 (14)	148

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

Acknowledgements

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

Funding information

This paper 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)].

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Eren, B., Demir, S., Dal, H. & Hökelek, T. (2014). Acta Cryst. E70, o238–o239. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Demukhamedova, S. D., Alieva, I. N., Godjaev, N. M., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2020). CrystEngComm, 22, 628–633. Web of Science CSD CrossRef CAS Google Scholar
Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ, 2, 563–574. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
He, J., Shi, L., Liu, S., Jia, P., Wang, J. & Hu, R. (2014). Monatsh. Chem. 145, 213–216. Web of Science CrossRef CAS PubMed Google Scholar
Khalilov, A. N., Khrustalev, V. N., Tereshina, T. A., Akkurt, M., Rzayev, R. M., Akobirshoeva, A. A. & Mamedov, İ. G. (2022). Acta Cryst. E78, 525–529. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, G.-N., Niu, Z.-G., Huang, M.-Q., Zou, Y. & Hu, L.-J. (2013). Acta Cryst. E69, o677. CSD CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Akkurt, M., Askerov, R. K., Mamedov, I. G., Rzayev, R. M., Chyrka, T. & Maharramov, A. M. (2020). Acta Cryst. E76, 720–723. Web of Science CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Khrustalev, V. N., Novikov, A. P., Akkurt, M., Rzayev, R. M., Akobirshoeva, A. A. & Mamedov, I. G. (2022). Acta Cryst. E78, 554–558. CSD CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Tereshina, T. A., Khrustalev, V. N., Akkurt, M., Rzayev, R. M., Akobirshoeva, A. A. & Mamedov, İ. G. (2021). Acta Cryst. E77, 516–521. Web of Science CSD CrossRef IUCr Journals Google Scholar
Paul, N. & Muthusubramanian, S. (2013). Synth. Commun. 43, 1200–1209. Web of Science CrossRef CAS Google Scholar
Ravindran, G., Muthusubramanian, S., Selvaraj, S. & Perumal, S. (2007). J. Heterocycl. Chem. 44, 133–136. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sabari, V., Selvakumar, R., Bakthadoss, M. & Aravindhan, S. (2012). Acta Cryst. E68, o2265. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shikhaliyev, N. Q., Kuznetsov, M. L., Maharramov, A. M., Gurbanov, A. V., Ahmadova, N. E., Nenajdenko, V. G., Mahmudov, K. T. & Pombeiro, A. J. L. (2019). CrystEngComm, 21, 5032–5038. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. https://Hirshfeldsurface.net. Google Scholar
Viswanathan, A., Kute, D., Musa, A., Konda Mani, S., Sipilä, V., Emmert-Streib, F., Zubkov, F. I., Gurbanov, A. V., Yli-Harja, O. & Kandhavelu, M. (2019). Eur. J. Med. Chem. 166, 291–303. Web of Science CrossRef CAS PubMed Google Scholar
Yan, H., Tan, H. & Xin, H. (2014). Heterocycles, 89, 359–373. Web of Science CSD CrossRef Google Scholar
Zeng, D. X. & Chen, Y. (2006). Synlett, pp. 0490–0492. Google Scholar
Zubkov, F. I., Mertsalov, D. F., Zaytsev, V. P., Varlamov, A. V., Gurbanov, A. V., Dorovatovskii, P. V., Timofeeva, T. V., Khrustalev, V. N. & Mahmudov, K. T. (2018). J. Mol. Liq. 249, 949–952. Web of Science CSD CrossRef CAS Google Scholar

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