research communications
and Hirshfeld surface analysis of 3-(hydroxymethyl)-3-methyl-2,6-diphenylpiperidin-4-one
aScience-Technology Research and Application Center, Artvin Coruh University, Artvin, Turkey, bDepartment of Chemistry and Chemical Technologies, Faculty of Natural and Agricultural Sciences, Atyrau State University named after Kh. Dosmukhamedov, 060011, Atyrau, Kazakhstan, cSamsun University, Faculty of Engineering, Department of Fundamental Sciences, 55420, Samsun, Turkey, dOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, eDepartment of Computer and Electronic Engineering Technology, Sanaa Community College, Sanaa, Yemen, and fDepartment of Electrical and Electronic Engineering, Faculty of Engineering, Ondokuz Mayıs University, 55139, Samsun, Turkey
*Correspondence e-mail: sevgi.kansiz@samsun.edu.tr, eiad.saif@scc.edu.ye
A new synthesis of the title compound, C19H21NO2, was developed with good yield and purity using the reaction of 4-hydroxy-3-methyl-2-butanone, benzaldehyde and ammonium acetate in glacial acetic acid as a solvent. The central piperidine ring adopts a chair conformation, and its least-squares basal plane forms dihedral angles of 85.71 (11) and 77.27 (11)° with the terminal aromatic rings. In the crystal, the molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into double ribbons. The Hirshfeld surface analysis shows that the most important contributions are from H⋯H (68%), C⋯H/H⋯C (19%) and O⋯H/H⋯O (12%) interactions.
Keywords: crystal structure; piperidone; benzaldehyde; 4-hydroxy-3-methyl-2-butanone; ammonium acetate; Hirshfeld surface; hydrogen bonding.
CCDC reference: 2124980
1. Chemical context
Many piperidine derivatives are found to possess pharmacological activity and are constituents of important drugs. Numerous biological effects including antiviral, antitumor, bactericidal, fungicidal and anti-inflammatory activities have been reported for these compounds (Kappe, 2000; Rameshkumar et al., 2003; Sasitha & John, 2021). In this work, a new protocol for the synthesis of diphenylpiperidin-4-one from 4-hydroxy-3-methyl-2-butanone, benzaldehyde and ammonium acetate under mild reaction conditions was developed. In addition, 3-(hydroxymethyl)-3-methyl-2,6-diphenylpiperidin-4-one was characterized by single crystal X-ray diffraction and studied by Hirshfeld surface analysis.
2. Structural commentary
The title compound, C19H21NO2, crystallizes in the Pna21 with one molecule in the of the cell. As shown in Fig. 1, it involves two terminal aromatic rings (C1–C6 and C14–C19) and a central piperidinone fragment (N1/C7–C10/Cl3/O1). The piperidine ring adopts a chair conformation, with the carbonyl O1 and the N-bound H1 atoms being in the equatorial positions. The least-squares basal plane of the piperidine ring (C7, C8, C10, C13) makes dihedral angles of 85.71 (11) and 77.27 (11)°, respectively, with the planes of the C1–C6 and C14–C19 aromatic rings.
3. Supramolecular features
In the crystal, molecules of the title compound are linked by strong O—H⋯O and weak C—H⋯O hydrogen bonds (Table 1) into double ribbons stretched along the c-axis direction (Fig. 2). Neighbouring molecules in the ribbon are related by the 21 screw axis. Besides this, the molecules are connected by N1—H1⋯C3 contacts into chains along the b-axis direction, thus layers perpendicular to the a axis are formed. No π–π or C—H⋯π interactions are present in this structure.
4. Database survey
A search of the Cambridge Structural Database (CSD Version 5.42, update of May 2021; Groom et al., 2016) revealed several related structures, viz. dimethyl-3-(2-hydroxyethyl)-9-oxo-7-phenylethyl-6,8-diphenyl-3,7-diazabicyclo(3.3.1)nonane-1,5-dicarboxylate (BACLUM; Caujolle et al., 1981), dimethyl-3-methyl-2,4-bis(4-nitrophenyl)-9-oxo-7-(1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylate (DEZTEK; Rossetti et al., 2018) and dimethyl-2,4-bis(2-methoxyphenyl)-3,7-dimethyl-3,7-diazabicyclo(3.3.1)nonan-9-one-1,5-dicarboxylate (REXNUD; Comba et al., 1997). In these three structures, the piperidine rings adopt a chair conformation, as in the title compound.
5. Hirshfeld surface analysis
The Hirshfeld surface analysis of the title compound was performed using Crystal Explorer 17 (Turner et al., 2017; Spackman & Jayatilaka, 2009). Fig. 3 shows the 3D surface mapped over dnorm over the range −0.5456 (red) to 1.6913 (blue) a.u. The large and small red spots indicate the O—H⋯O and C—H⋯O interactions. The two-dimensional fingerprint plots, shown in Fig. 4, present all interactions and those delineated into H⋯H (68%), C⋯H/H⋯C (19%) and O⋯H/H⋯O (12%) components.
6. Synthesis and crystallization
The title compound was prepared (Fig. 5) according to the procedure reported in the literature for preparation of diphenylpiperidin-4-one (Kim & Tulemisova, 1997). To a mixture of 3.03 g (0.03 mol) of 4-hydroxy-3-methyl-2-butanone and 6.04 g (0.06 mol) of benzaldehyde in glacial acetic acid as a solvent, kept at 293–298 K until the initial keto alcohol disappears as indicated by TLC (1.5 h), 2.3 g (0.03 mol) of ammonium acetate was added. Then the mixture was stirred at the same temperature for 6–7 h. The formed white precipitate was separated and after acidification of the solution with 5% hydrochloric acid to pH 4, the hydrochlorides were converted to bases by neutralization with K2CO3 in a strongly basic reaction. After the extraction with diethyl ether of the by-product base (control of the completeness of extraction by TLC), the title compound was extracted with chloroform. After drying the chloroform extracts and distilling off the solvent, a white crystalline compound was obtained (5.95 g, 70%), readily soluble in chloroform, acetone, and hot ethanol (Fig. 5).
7. Refinement
Crystal data, data collection and structure . The N-bound H atom was refined freely. The O-bound H atom was located in a difference-Fourier map and refined with O—H = 0.82 Å, and with Uiso(H) = 1.5Ueq(O). The C-bound H atoms were positioned geometrically (C—H = 0.93, 0.96, 0.97 and 0.98 Å for sp2-hybridized, methyl, methylene and methine C atoms, respectively) and refined using a riding model, with Uiso(H) = 1.5Ueq(C) and 1.2Ueq(C) for methyl and other H atoms, respectively.
details are summarized in Table 2Supporting information
CCDC reference: 2124980
https://doi.org/10.1107/S2056989021012640/yk2159sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021012640/yk2159Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021012640/yk2159Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).C19H21NO2 | Dx = 1.212 Mg m−3 |
Mr = 295.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 17006 reflections |
a = 17.3298 (8) Å | θ = 1.9–31.5° |
b = 14.1856 (7) Å | µ = 0.08 mm−1 |
c = 6.5857 (3) Å | T = 296 K |
V = 1618.99 (13) Å3 | Prism, colorless |
Z = 4 | 0.72 × 0.57 × 0.33 mm |
F(000) = 632 |
Stoe IPDS 2 diffractometer | 4763 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3441 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.042 |
rotation method scans | θmax = 31.2°, θmin = 1.9° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −24→25 |
Tmin = 0.958, Tmax = 0.973 | k = −20→20 |
17314 measured reflections | l = −7→9 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0515P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4763 reflections | Δρmax = 0.16 e Å−3 |
204 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.8 (5) |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.52068 (8) | −0.46901 (9) | −0.4103 (2) | 0.0600 (4) | |
O2 | −0.60074 (9) | −0.40945 (10) | −0.0228 (2) | 0.0610 (4) | |
H2 | −0.565229 | −0.447609 | −0.026638 | 0.091* | |
N1 | −0.58527 (9) | −0.20075 (10) | −0.4826 (2) | 0.0446 (3) | |
C14 | −0.69489 (10) | −0.21260 (11) | −0.2492 (3) | 0.0421 (4) | |
C9 | −0.54765 (10) | −0.39351 (11) | −0.4587 (3) | 0.0417 (4) | |
C13 | −0.61836 (10) | −0.25456 (10) | −0.3131 (3) | 0.0396 (3) | |
H13 | −0.582802 | −0.250220 | −0.197803 | 0.048* | |
C6 | −0.47125 (11) | −0.16339 (12) | −0.6872 (3) | 0.0483 (4) | |
C10 | −0.62508 (9) | −0.36075 (11) | −0.3756 (3) | 0.0388 (3) | |
C11 | −0.64790 (12) | −0.42148 (12) | −0.1929 (3) | 0.0482 (4) | |
H11A | −0.700646 | −0.406616 | −0.155468 | 0.058* | |
H11B | −0.646451 | −0.487258 | −0.233009 | 0.058* | |
C7 | −0.50597 (10) | −0.22790 (12) | −0.5292 (3) | 0.0453 (4) | |
H7 | −0.474939 | −0.224784 | −0.404983 | 0.054* | |
C19 | −0.74209 (11) | −0.16475 (13) | −0.3861 (3) | 0.0515 (4) | |
H19 | −0.725854 | −0.156467 | −0.519485 | 0.062* | |
C8 | −0.50769 (11) | −0.32968 (13) | −0.6060 (3) | 0.0484 (4) | |
H8A | −0.534221 | −0.331932 | −0.735585 | 0.058* | |
H8B | −0.455272 | −0.351604 | −0.626845 | 0.058* | |
C12 | −0.68510 (11) | −0.37561 (13) | −0.5433 (3) | 0.0508 (4) | |
H12A | −0.674874 | −0.333097 | −0.653506 | 0.076* | |
H12B | −0.735741 | −0.363652 | −0.490172 | 0.076* | |
H12C | −0.682287 | −0.439401 | −0.591446 | 0.076* | |
C15 | −0.72036 (12) | −0.22177 (14) | −0.0520 (3) | 0.0555 (5) | |
H15 | −0.688985 | −0.251458 | 0.043011 | 0.067* | |
C18 | −0.81260 (13) | −0.12956 (14) | −0.3257 (4) | 0.0638 (6) | |
H18 | −0.843205 | −0.097262 | −0.418500 | 0.077* | |
C1 | −0.51207 (14) | −0.13749 (15) | −0.8595 (4) | 0.0630 (5) | |
H1A | −0.562927 | −0.157131 | −0.875089 | 0.076* | |
C17 | −0.83831 (13) | −0.14174 (16) | −0.1288 (4) | 0.0692 (6) | |
H17 | −0.886403 | −0.119157 | −0.089324 | 0.083* | |
C3 | −0.40316 (15) | −0.05295 (15) | −0.9865 (4) | 0.0730 (7) | |
H3 | −0.379964 | −0.017017 | −1.087645 | 0.088* | |
C16 | −0.79174 (14) | −0.18768 (16) | 0.0075 (4) | 0.0687 (6) | |
H16 | −0.808210 | −0.195995 | 0.140665 | 0.082* | |
C2 | −0.47809 (16) | −0.08286 (16) | −1.0084 (4) | 0.0717 (6) | |
H2A | −0.505992 | −0.066302 | −1.123614 | 0.086* | |
C5 | −0.39677 (12) | −0.13063 (17) | −0.6673 (5) | 0.0715 (7) | |
H5 | −0.368693 | −0.145511 | −0.551306 | 0.086* | |
C4 | −0.36317 (14) | −0.07616 (19) | −0.8164 (5) | 0.0847 (9) | |
H4 | −0.312707 | −0.055149 | −0.800405 | 0.102* | |
H1 | −0.5902 (17) | −0.140 (2) | −0.450 (5) | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0654 (9) | 0.0459 (7) | 0.0686 (9) | 0.0199 (6) | 0.0128 (8) | 0.0080 (6) |
O2 | 0.0811 (10) | 0.0618 (7) | 0.0400 (7) | 0.0271 (7) | −0.0050 (7) | 0.0015 (6) |
N1 | 0.0489 (8) | 0.0368 (6) | 0.0480 (9) | 0.0024 (6) | 0.0031 (7) | 0.0004 (6) |
C14 | 0.0454 (9) | 0.0369 (7) | 0.0439 (9) | 0.0037 (7) | −0.0020 (8) | −0.0021 (6) |
C9 | 0.0468 (9) | 0.0383 (7) | 0.0399 (8) | 0.0044 (7) | −0.0039 (7) | −0.0052 (6) |
C13 | 0.0428 (9) | 0.0376 (7) | 0.0383 (8) | 0.0038 (6) | −0.0031 (7) | 0.0005 (7) |
C6 | 0.0484 (10) | 0.0428 (8) | 0.0537 (11) | −0.0033 (7) | 0.0038 (9) | −0.0028 (8) |
C10 | 0.0424 (8) | 0.0370 (7) | 0.0372 (8) | 0.0030 (6) | −0.0040 (7) | 0.0002 (6) |
C11 | 0.0524 (10) | 0.0425 (8) | 0.0495 (10) | 0.0046 (7) | 0.0047 (9) | 0.0050 (7) |
C7 | 0.0448 (9) | 0.0468 (8) | 0.0441 (9) | −0.0011 (7) | −0.0013 (8) | −0.0006 (8) |
C19 | 0.0549 (11) | 0.0475 (9) | 0.0521 (10) | 0.0092 (8) | −0.0043 (9) | 0.0034 (8) |
C8 | 0.0478 (10) | 0.0465 (9) | 0.0509 (10) | 0.0044 (8) | 0.0061 (8) | −0.0008 (8) |
C12 | 0.0536 (11) | 0.0482 (9) | 0.0507 (10) | 0.0017 (8) | −0.0117 (9) | −0.0064 (8) |
C15 | 0.0594 (11) | 0.0600 (10) | 0.0471 (11) | 0.0121 (9) | 0.0023 (9) | 0.0022 (9) |
C18 | 0.0584 (12) | 0.0527 (10) | 0.0803 (16) | 0.0175 (9) | −0.0110 (11) | 0.0034 (11) |
C1 | 0.0735 (14) | 0.0611 (11) | 0.0544 (12) | −0.0208 (10) | −0.0075 (11) | 0.0033 (10) |
C17 | 0.0518 (12) | 0.0604 (11) | 0.0954 (19) | 0.0141 (10) | 0.0101 (13) | −0.0121 (12) |
C3 | 0.0806 (16) | 0.0533 (10) | 0.0851 (18) | 0.0009 (10) | 0.0272 (14) | 0.0154 (12) |
C16 | 0.0682 (13) | 0.0748 (13) | 0.0632 (14) | 0.0105 (11) | 0.0176 (12) | −0.0050 (11) |
C2 | 0.0980 (17) | 0.0631 (12) | 0.0540 (13) | −0.0150 (12) | −0.0030 (12) | 0.0060 (11) |
C5 | 0.0459 (12) | 0.0746 (14) | 0.0940 (19) | −0.0035 (10) | −0.0049 (12) | 0.0283 (14) |
C4 | 0.0533 (13) | 0.0824 (16) | 0.119 (3) | −0.0099 (11) | 0.0055 (15) | 0.0365 (17) |
O1—C9 | 1.211 (2) | C19—H19 | 0.9300 |
O2—C11 | 1.397 (2) | C8—H8A | 0.9700 |
O2—H2 | 0.8200 | C8—H8B | 0.9700 |
N1—C7 | 1.460 (2) | C12—H12A | 0.9600 |
N1—C13 | 1.469 (2) | C12—H12B | 0.9600 |
N1—H1 | 0.90 (3) | C12—H12C | 0.9600 |
C14—C15 | 1.378 (3) | C15—C16 | 1.385 (3) |
C14—C19 | 1.394 (3) | C15—H15 | 0.9300 |
C14—C13 | 1.513 (2) | C18—C17 | 1.382 (4) |
C9—C8 | 1.497 (3) | C18—H18 | 0.9300 |
C9—C10 | 1.522 (2) | C1—C2 | 1.381 (3) |
C13—C10 | 1.566 (2) | C1—H1A | 0.9300 |
C13—H13 | 0.9800 | C17—C16 | 1.372 (4) |
C6—C5 | 1.378 (3) | C17—H17 | 0.9300 |
C6—C1 | 1.387 (3) | C3—C4 | 1.358 (4) |
C6—C7 | 1.511 (3) | C3—C2 | 1.374 (4) |
C10—C12 | 1.532 (3) | C3—H3 | 0.9300 |
C10—C11 | 1.531 (2) | C16—H16 | 0.9300 |
C11—H11A | 0.9700 | C2—H2A | 0.9300 |
C11—H11B | 0.9700 | C5—C4 | 1.379 (4) |
C7—C8 | 1.530 (3) | C5—H5 | 0.9300 |
C7—H7 | 0.9800 | C4—H4 | 0.9300 |
C19—C18 | 1.379 (3) | ||
C11—O2—H2 | 109.5 | C9—C8—C7 | 111.45 (15) |
C7—N1—C13 | 112.98 (14) | C9—C8—H8A | 109.3 |
C7—N1—H1 | 113.2 (19) | C7—C8—H8A | 109.3 |
C13—N1—H1 | 107 (2) | C9—C8—H8B | 109.3 |
C15—C14—C19 | 117.87 (17) | C7—C8—H8B | 109.3 |
C15—C14—C13 | 120.38 (16) | H8A—C8—H8B | 108.0 |
C19—C14—C13 | 121.74 (17) | C10—C12—H12A | 109.5 |
O1—C9—C8 | 121.79 (16) | C10—C12—H12B | 109.5 |
O1—C9—C10 | 121.04 (16) | H12A—C12—H12B | 109.5 |
C8—C9—C10 | 117.15 (14) | C10—C12—H12C | 109.5 |
N1—C13—C14 | 110.43 (13) | H12A—C12—H12C | 109.5 |
N1—C13—C10 | 109.24 (13) | H12B—C12—H12C | 109.5 |
C14—C13—C10 | 112.72 (13) | C14—C15—C16 | 121.3 (2) |
N1—C13—H13 | 108.1 | C14—C15—H15 | 119.3 |
C14—C13—H13 | 108.1 | C16—C15—H15 | 119.3 |
C10—C13—H13 | 108.1 | C19—C18—C17 | 120.7 (2) |
C5—C6—C1 | 117.8 (2) | C19—C18—H18 | 119.6 |
C5—C6—C7 | 120.78 (19) | C17—C18—H18 | 119.6 |
C1—C6—C7 | 121.40 (17) | C2—C1—C6 | 120.8 (2) |
C9—C10—C12 | 107.29 (14) | C2—C1—H1A | 119.6 |
C9—C10—C11 | 109.78 (14) | C6—C1—H1A | 119.6 |
C12—C10—C11 | 108.28 (15) | C16—C17—C18 | 118.9 (2) |
C9—C10—C13 | 108.82 (13) | C16—C17—H17 | 120.5 |
C12—C10—C13 | 111.86 (13) | C18—C17—H17 | 120.5 |
C11—C10—C13 | 110.75 (14) | C4—C3—C2 | 119.6 (2) |
O2—C11—C10 | 114.21 (15) | C4—C3—H3 | 120.2 |
O2—C11—H11A | 108.7 | C2—C3—H3 | 120.2 |
C10—C11—H11A | 108.7 | C17—C16—C15 | 120.4 (2) |
O2—C11—H11B | 108.7 | C17—C16—H16 | 119.8 |
C10—C11—H11B | 108.7 | C15—C16—H16 | 119.8 |
H11A—C11—H11B | 107.6 | C3—C2—C1 | 120.1 (3) |
N1—C7—C6 | 111.10 (15) | C3—C2—H2A | 119.9 |
N1—C7—C8 | 107.46 (14) | C1—C2—H2A | 119.9 |
C6—C7—C8 | 110.59 (16) | C4—C5—C6 | 121.1 (2) |
N1—C7—H7 | 109.2 | C4—C5—H5 | 119.4 |
C6—C7—H7 | 109.2 | C6—C5—H5 | 119.4 |
C8—C7—H7 | 109.2 | C3—C4—C5 | 120.5 (2) |
C18—C19—C14 | 120.7 (2) | C3—C4—H4 | 119.7 |
C18—C19—H19 | 119.7 | C5—C4—H4 | 119.7 |
C14—C19—H19 | 119.7 | ||
C7—N1—C13—C14 | 170.51 (14) | C1—C6—C7—N1 | −44.8 (2) |
C7—N1—C13—C10 | −64.98 (17) | C5—C6—C7—C8 | −103.5 (2) |
C15—C14—C13—N1 | −152.01 (17) | C1—C6—C7—C8 | 74.5 (2) |
C19—C14—C13—N1 | 28.7 (2) | C15—C14—C19—C18 | −1.2 (3) |
C15—C14—C13—C10 | 85.5 (2) | C13—C14—C19—C18 | 178.07 (17) |
C19—C14—C13—C10 | −93.80 (19) | O1—C9—C8—C7 | −133.78 (19) |
O1—C9—C10—C12 | −102.5 (2) | C10—C9—C8—C7 | 47.8 (2) |
C8—C9—C10—C12 | 75.99 (19) | N1—C7—C8—C9 | −54.0 (2) |
O1—C9—C10—C11 | 15.0 (2) | C6—C7—C8—C9 | −175.41 (15) |
C8—C9—C10—C11 | −166.55 (15) | C19—C14—C15—C16 | 2.3 (3) |
O1—C9—C10—C13 | 136.33 (17) | C13—C14—C15—C16 | −177.03 (19) |
C8—C9—C10—C13 | −45.2 (2) | C14—C19—C18—C17 | −0.6 (3) |
N1—C13—C10—C9 | 50.76 (17) | C5—C6—C1—C2 | 1.8 (3) |
C14—C13—C10—C9 | 173.93 (15) | C7—C6—C1—C2 | −176.3 (2) |
N1—C13—C10—C12 | −67.59 (18) | C19—C18—C17—C16 | 1.4 (4) |
C14—C13—C10—C12 | 55.57 (19) | C18—C17—C16—C15 | −0.4 (4) |
N1—C13—C10—C11 | 171.52 (14) | C14—C15—C16—C17 | −1.5 (3) |
C14—C13—C10—C11 | −65.32 (18) | C4—C3—C2—C1 | −1.0 (4) |
C9—C10—C11—O2 | 67.49 (18) | C6—C1—C2—C3 | −0.4 (4) |
C12—C10—C11—O2 | −175.68 (14) | C1—C6—C5—C4 | −1.8 (4) |
C13—C10—C11—O2 | −52.70 (19) | C7—C6—C5—C4 | 176.2 (2) |
C13—N1—C7—C6 | −173.39 (15) | C2—C3—C4—C5 | 1.0 (4) |
C13—N1—C7—C8 | 65.51 (18) | C6—C5—C4—C3 | 0.5 (4) |
C5—C6—C7—N1 | 137.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.05 | 2.8194 (18) | 156 |
C8—H8A···O2ii | 0.97 | 2.47 | 3.379 (3) | 155 |
N1—H1···C3iii | 0.90 (3) | 2.75 (3) | 3.605 (2) | 161 (3) |
Symmetry codes: (i) −x−1, −y−1, z+1/2; (ii) x, y, z−1; (iii) −x−1, −y, z+1/2. |
Acknowledgements
Author contributions are as follows. Conceptualization, MKG, SK, and ES; synthesis, MKG and GBT; writing (review and editing of the manuscript) MKG and SK; formal analysis, MKG, SK and ND; crystal-structure determination, MKG, SK and ND; validation, MKG, GBT and ES; project administration, MKG and SK. MKG thanks the Ministry of Education and Science of the Republic of Kazakhstan for financial support as a visiting professor at Atyrau State University.
References
Caujolle, R., Lattes, A., Jaud, J. & Galy, J. (1981). Acta Cryst. B37, 1699–1703. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Comba, P., Nuber, B. & Ramlow, A. (1997). J. Chem. Soc. Dalton Trans. pp. 347–352. CSD CrossRef Web of Science 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
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043–1052. Web of Science CrossRef PubMed CAS Google Scholar
Kim, D. G. & Tulemisova, G. B. (1997). Russ. J. Org. Chem. 33, 1337–1340. CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rameshkumar, N., Veena, A., Ilavarasan, R., Adiraj, M., Shanmugapandiyan, P. & Sridhar, S. K. (2003). Biol. Pharm. Bull. 26, 188–193. Web of Science CrossRef PubMed CAS Google Scholar
Rossetti, A., Landoni, S., Meneghetti, F., Castellano, C., Mori, M., Colombo Dugoni, G. & Sacchetti, A. (2018). New J. Chem. 42, 12072–12081. Web of Science CSD CrossRef CAS Google Scholar
Sasitha, T. & John, W. J. (2021). Heliyon, 7, e06127. Web of Science CrossRef PubMed 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
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). Crystal Explorer 17.5. University of Western Australia. https://hirshfeldsurface.net. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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