The whole molecule of the title compound is generated by twofold rotational symmetry. In the crystal, molecules are linked by intermolecular C—H⋯O interactions with
(12) ring motifs, and C—H⋯π interactions, resulting in ribbons along the c-axis direction. The molecular packing is consolidated by van der Waals interactions between these ribbons.
Keywords: crystal structure, C—H⋯O hydrogen bonds, C—H⋯··π interactions, van der Waals interactions, Hirshfeld surface
Abstract
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 R 2 2(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.
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 +
); 2.51 Å, 158°] interactions with
(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)
; (ii)
; (iii)
.
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,
− z; (c) x +
, −y +
, −z + 1; (d) 1 − x, 1 − y, −z; (e) 1 − x, 1 − y, 1 − z; (f) x, 1 − y, −
+ z; (g) x, 1 − y,
+ 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. 5 ▸ b–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, P b c n |
| 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 ▸) |
| 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[F 2 > 2σ(F 2)], wR(F 2), S | 0.051, 0.142, 1.09 |
| No. of reflections | 1834 |
| No. of parameters | 115 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.29, −0.23 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989022005382/tx2050sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022005382/tx2050Isup2.hkl
CCDC reference: 2173928
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
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.
supplementary crystallographic information
Crystal data
| C22H19NO2 | Dx = 1.281 Mg m−3 |
| Mr = 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
| XtaLAB Synergy, Dualflex, HyPix diffractometer | 1746 reflections with I > 2σ(I) |
| Radiation source: micro-focus sealed X-ray tube | Rint = 0.034 |
| φ and ω scans | θmax = 79.4°, θmin = 4.3° |
| Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021) | h = −26→26 |
| Tmin = 0.906, Tmax = 0.939 | k = −11→10 |
| 21247 measured reflections | l = −10→11 |
| 1834 independent reflections |
Refinement
| 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(Fo2) + (0.0811P)2 + 0.6375P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max < 0.001 |
| 1834 reflections | Δρmax = 0.28 e Å−3 |
| 115 parameters | Δρmin = −0.23 e Å−3 |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| 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)
| 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)
| 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)
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···Cg1iv | 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.
Funding Statement
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)].
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989022005382/tx2050sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022005382/tx2050Isup2.hkl
CCDC reference: 2173928
Additional supporting information: crystallographic information; 3D view; checkCIF report