Crystal structure and Hirshfeld surface analyses, inter­action energy calculations and energy frameworks of methyl 2-[(4-cyano­phen­yl)meth­oxy]quinoline-4-carboxyl­ate

El-Mrabet, A.; Haoudi, A.; Capet, F.; Hökelek, T.; Ahmed, M.

doi:10.1107/S2056989025005547

research communications

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ISSN: 2056-9890

Volume 81| Part 7| July 2025| Pages 650-656

https://doi.org/10.1107/S2056989025005547

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Crystal structure and Hirshfeld surface analyses, interaction energy calculations and energy frameworks of methyl 2-[(4-cyanophenyl)methoxy]quinoline-4-carboxylate

Ayoub El-Mrabet,^a ^* Amal Haoudi,^a Frederic Capet,^b Tuncer Hökelek ^c and Mazzah Ahmed ^d

^aLaboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty Of Science And Technology, Road Immouzer, BP 2202 Fez, Morocco, ^bUniversity of Lille, CNRS, UMR 8181, UCCS, Unité de Catalyse et Chimie du Solide, F-59000 Lille, France, ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye, and ^dUniversité de Lille, CNRS, UAR 3290, MSAP, Miniaturization for Synthesis, Analysis and Proteomics, F-59000 Lille, France
^*Correspondence e-mail: [email protected]

Edited by K. V. Domasevitch, National Taras Shevchenko University of Kyiv, Ukraine (Received 21 March 2025; accepted 19 June 2025; online 27 June 2025)

The title compound, C₁₉H₁₄N₂O₃, features competition and interplay of a range of weak interactions, which actualize under the absence of conventional hydrogen-bond donors. Two kinds of stacking interactions, namely slipped antiparallel interactions of cyanophenyl groups as well as quinoline and carboxy groups, are primarily important. In combination with relatively short tetrel OCH₃⋯N≡C bonds [C⋯N = 3.146 (3) Å] they are responsible for the generation of the layers, while the interlayer bonding occurs via C—H⋯O and C—H⋯N weak hydrogen bonds. These findings are consistent with the results of Hirshfeld surface analysis and calculated interaction energies. Contributions of the C⋯C, C⋯N/N⋯C and C⋯O/O⋯C contacts originating in the stacking interactions account for 17.0% to the surface area. The largest interactions energies are associated with the two kinds of stacks (−45.8 and −24.3 kJ mol⁻¹) and they are superior to the energies of weak hydrogen bond and tetrel interactions (−12.4 to −22.4 kJ mol⁻¹). Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated via the dispersion energy contributions.

Keywords: quinoline; π-stacking; weak hydrogen bond; tetrel bond; crystal structure.

CCDC reference: 2465703

1. Chemical context

Heterocyclic compounds, especially nitrogen-containing systems such as quinoline derivatives, play a pivotal role in medicinal chemistry due to their broad spectrum of biological activities (Filali Baba et al., 2019 , 2020 ; Hayani et al., 2021a ; El-Mrabet et al., 2023 , 2025 ; Bouzian et al., 2018 , 2021 ). These compounds exhibit antimicrobial (Salam et al., 2023 ), antifungal (Chen et al., 2021 ), anti-Alzheimer's (Chen et al., 2023 ), anti-infective (Muruganantham et al., 2004 ), antileishmanial (Chanquia et al., 2019 ), anti-HIV (Strekowski et al., 1991 ), anti-inflammatory (Ghanim et al., 2022 ), antiviral (Kaur & Kumar, 2021 ), and corrosion inhibitive activities (Mahamoud et al., 2006 ; Filali Baba et al., 2016a ,b ). Their structural flexibility and ability to interact with diverse biological targets make quinolines attractive frameworks for drug development, especially in addressing significant therapeutic challenges. In this context, we report herein the synthesis and comprehensive structural characterization of a novel quinoline-based compound, methyl 2-(4-cyanobenzyloxy)quinoline-4-carboxylate (I). The target molecule was obtained via an O-alkylation reaction of methyl 2-oxo-1,2-dihydroquinoline-4-carboxylate with 4-(bromomethyl)benzonitrile under phase-transfer catalysis (PTC). The synthesized compound was analyzed using ¹H and ¹³C NMR, FT-IR spectroscopy, single-crystal X-ray diffraction, and Hirshfeld surface analysis to elucidate its molecular and crystal structure.

2. Structural commentary

The title compound, (I), contains the almost planar quinoline and cyanophenyl moieties (Fig. 1), where the planar A (C1–C6), B (N1/C1/C6–C9) and C (C13–C18) rings are oriented at dihedral angles of A/B = 0.56 (5)°, A/C = 14.47 (6)° and B/C = 15.02 (6)°. The exocyclic atoms O1, O2, O3, C10, C11 and C12 are also nearly coplanar with the quinoline framework and lie 0.005 (2), −0.030 (2), 0.016 (1), −0.015 (2), −0.067 (3) and −0.037 (2) Å, respectively, away from its mean plane.

Figure 1
The molecular structure of the title compound, with the atom and ring labelling schemes and displacement ellipsoids drawn at the 50% probability level. The dotted line indicates a possible weak hydrogen bond.

In the ester group, the O1—C10 and O2—C10 bond lengths are 1.177 (2) Å and 1.308 (2) Å, respectively. This strict differentiation of the C—O bonds indicates mainly the localized single and double bounds rather than delocalized bonding arrangement. The O1—C10—O2 bond angle of 121.6 (2)° agrees well with the parameters for comparable methyl 2-phenyl quinoline-4-carboxylate [122.42 (14)°; Mague et al., 2016 ], and methyl 2-oxo-1-(propyn-2-yl)-1,2-di hydroquinoline-4-carboxylate [122.55 (12)°; El-Mrabet et al., 2023]. The planes of the carbomethoxy group [defined by the atoms C7, C10, O1 and O2] and ring B are related by 0.96 (17)° indicating a coplanar arrangement. The latter is partly caused by the weak intramolecular C5—H5⋯O1 hydrogen bond (Table 1), similarly to in methyl 6-chloro-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxylate with a corresponding dihedral angle of 4.08 (8)° (Filali Baba et al., 2022 ). As evidenced by the C11—O2—C10—C7 [178.98 (18)°] torsion angle, the ester group attached to the quinoline moiety is in a syn peripheral conformation. The corresponding torsion angles for the related derivatives of benzyl [176.06 (11)°; Bouzian et al., 2018] and ethyl [−176.71 (15)°; Sunitha et al., 2015 ] quinoline-4-carboxylates represent syn- and anti-peripheral conformations, respectively.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.93	2.75	3.651 (2)	163
C5—H5⋯O1	0.93	2.25	2.883 (2)	125
C15—H15⋯O1ⁱⁱ	0.93	2.48	3.337 (2)	154
C18—H18⋯N2ⁱⁱⁱ	0.93	2.68	3.558 (3)	158
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

3. Supramolecular features

In the crystal, intermolecular C15—H15⋯O1ⁱⁱ hydrogen bonds [symmetry code (ii): x + 1, y + $[{1\over 2}]$ , z + $[{3\over 2}]$ ; Table 1] link the molecules into the infinite chains along the b-axis direction (Fig. 2). However, the entire non-covalent framework in the structure may be best described as consisting of corrugated layers, which propagate parallel to the ac plane and are linked in the third dimension by a set of very weak hydrogen bonds. The layers themselves are sustained by two kinds of stacking interactions. First, two inversion-related cyanophenyl moieties [symmetry code: (v) −x + 1, −y + 1, −z + 1] afford antiparallel stacks with interplanar distances of 3.660 (2) Å, in which the centroids of C19–N2 groups [Cg2] are situated almost exactly above the centroids of the corresponding aromatic rings (Cg1) at 3.735 (2) Å (Figs. 2, 3). The second kind of stacking interaction is identified between nearly parallel ester groups and heterocyclic rings B [symmetry code: (vi) x + $[{1\over 2}]$ , y, −z + $[{3\over 2}]$ ; interplanar angle is 3.98 (11)°], with separation Cg3⋯C10^vi = 3.817 (2) Å (Cg3 is the ring B centroid). These layers are further consolidated by relatively short tetrel bonding (Varadwaj et al., 2023 ) of the type OCH₃⋯N≡C [C11⋯N2^iv = 3.146 (3) Å, symmetry code (iv): −x + $[{1\over 2}]$ , −y + 1, x + $[{1\over 2}]$ ], which is well compatible to both stacking patterns (Fig. 3).

Figure 2
Fragment of the crystal structure showing hydrogen-bonded chains along the b-axis direction and stacking interactions between the adjacent chains. [Symmetry code (ii): x + 1, y + $[{1\over 2}]$ , z + $[{3\over 2}]$ .]

Figure 3
(a) Projection of the structure nearly on the ac-plane showing assembly of the layers by means of stacking interactions (indicated in blue) and tetrel bonds of the type OCH₃⋯N≡C (indicated with dotted red lines). (b) Packing of successive corrugated layers viewed in a projection on the bc-plane, with dotted lines representing interlayer weak hydrogen bonding. The individual layers are identified with blue and red colors. Cg1, Cg2 and Cg3 are centroids of the groups C13–C18, N2/C19 and N1/C1/C6–C9, respectively. [Symmetry codes: (iii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z; (v) −x + 1, −y + 1, −z + 1; (vi) x + $[{1\over 2}]$ , y, −z + $[{3\over 2}]$ .]

The resulting corrugated layers are separated by 7.849 Å, which is a half of the unit cell parameter b (Fig. 3). In addition to the above most prominent C15—H15⋯O1ⁱⁱ hydrogen bonds, the suite of interlayer interactions also comprises weaker C3—H3⋯O3ⁱ and C18—H18⋯N2ⁱⁱⁱ bonds [symmetry codes (i): x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , z; (iii) x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z; Table 1]. These interactions are also directional, with corresponding angles at the H atoms of 163 and 158°, respectively. No C—H⋯(ring) or π(ring)–(ring) interactions are observed. The title compound highlights rather the interplay of different kinds of stacking interactions, weak hydrogen and tetrel bonding for consolidating the 3D architecture. The combination of Hirshfeld surface analysis and energy framework calculations reveals dispersion energy as the dominant contributor, offering new insights into the packing features of quinoline-based systems and their potential in crystal engineering.

4. Hirshfeld surface analysis

For visualizing the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ). In the HS plotted over d_norm (Fig. 4), the contact distances equal, shorter and longer than the sum of van der Waals radii are shown in white, red and blue, respectively (Venkatesan et al., 2016 ). The brightest red spots correspond to the donor and acceptor sites of the C15—H15⋯O1ⁱⁱ bonds, whereas the positions of the tetrel OCH₃⋯N≡C bonds are also clearly visible as a pair of more diffuse red spots.

Figure 4
The Hirshfeld surface of the title compound mapped over d_norm.

The overall two-dimensional fingerprint plots and those delineated into the contributions of the individual types of the contacts (McKinnon et al., 2007 ) are shown in Fig. 5. Beyond the expected far dominant significance of H⋯H contacts (43.8%), the main contributors to the Hirshfeld surface are also associated with the H atoms: C⋯H/H⋯C = 14.3%, N⋯H/H⋯N = 14.1% and O⋯H/H⋯O = 9.9%. However, only the latter ones appear in the plots in the form of two relatively sharp spikes pointing to the lower left, thus indicating the hydrogen-bond interactions (shortest H⋯O = 2.35 Å). In the case of N⋯H/H⋯N contacts, these spikes are much shorter and diffuse, since most points originate rather in the tetrel interactions of methyl and cyano groups. In addition, the light-blue area centered at ca 3.80 Å in the plot for C⋯C contacts indicates the above stacking interactions. In total, the corresponding contacts, i.e. C⋯C, C⋯N/N⋯C and C⋯O/O⋯C, deliver as much as 17.0% to the surface area.

Figure 5
Two-dimensional fingerprint plots for the title compound: (a) all interactions and delineated into the principal contributions of (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) N⋯H/H⋯N, (f) C⋯C, (g) C⋯N/N⋯C and (h) C⋯O/O⋯C contacts. Other minor contributors are O⋯O (0.5%) and N⋯O/O⋯N (0.4%) contacts.

The nearest coordination environment of a molecule can be determined from the color patches on the HS based on how close to other molecules they are. The Hirshfeld surface representations of contact patches plotted onto the surface are shown for the H⋯H, H⋯C/C⋯H, H⋯ N/N⋯H, C⋯C and H⋯O/O⋯H interactions in Fig. S2a–e, respectively, in the supporting information. The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H, H⋯C/C⋯H, H⋯N/N⋯H, C⋯C and H⋯O/O⋯H interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

5. Interaction energy calculations and energy frameworks

The intermolecular interaction energies were calculated using the CE–B3LYP/6–31G(d,p) energy model available in Crystal Explorer 17.5 (Spackman et al., 2021), where a cluster of molecules is generated by applying crystallographic symmetry operations with respect to a selected central molecule within the radius of 3.8 Å by default (Turner et al., 2014 ). The total intermolecular energy (E_tot) is the sum of electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange-repulsion (E_rep) energies (Turner et al., 2015 ).

With a cut-off of |E_tot| > 12.0 kJ mol⁻¹, seven symmetry-independent paths were identified for the closest environment of the title molecules (Table 2). The highest energy E_tot = −45.8 kJ mol⁻¹ corresponds to the pairing pattern involving stacking of quinoline and carboxy groups (path A⋯B, Fig. 6). The primary contributor here is London dispersion (E_dis = −66.2 kJ mol⁻¹), due to the very large interaction area. Stacking of cyanophenyl moieties is perceptibly weaker with E_tot = −24.3 kJ mol⁻¹. This value approaches the parameter calculated for the slipped antiparallel dimer of nitrobenzene molecules (−28.2 kJ mol⁻¹; Tsuzuki et al., 2006 ). This stacking is also clearly distinguishable in the present energy landscape and it is even superior to the energies of the intermolecular interactions, which correspond to weak hydrogen bonding (−15.8 and −17.8 kJ mol⁻¹; Table 2). In the case of the A⋯D pair (Fig. 6), slightly higher total energy of −22.4 kJ mol⁻¹ is due to a combination of weak hydrogen bond C15—H15⋯O1ⁱⁱ and dispersion forces, with the corresponding principal contributors E_ele = −10.3 and E_dis = −25.3 kJ mol⁻¹. This is in line with larger interaction area and generation of additional vdW contacts, e.g. O2⋯C3ⁱⁱ = 3.534 (2) Å. Finally, the tetrel bonds OCH₃⋯N≡C (pair B⋯C, Fig. 6) are very similar in energy to the weak hydrogen bonds (E_tot = −12.4 kJ mol⁻¹) and therefore their significance to the crystal packing may be regarded as comparable.

Table 2
Calculated interaction energies (kJ mol⁻¹)

Interaction energies were calculated employing the CE-B3LYP/6–31G(d,p) functional/basis set combination. The scale factors used to determine E_tot are k_ele = 1.057, k_pol = 0.740, k_dis = 0.871, and k_rep = 0.618 (Mackenzie et al., 2017 ). R is the distance between the centroids of the interacting molecules.

Path	Symmetry code	Type^a	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
A⋯B	x + $[{1\over 2}]$ , y, −z + $[{3\over 2}]$	stacking	5.77	−5.3	−2.1	−66.2	30.8	−45.8
A⋯C	−x + 1, −y + 1, −z + 1	stacking	12.05	−6.1	−2.4	−25.1	9.3	−24.3
B⋯C	−x + $[{1\over 2}]$ , −y + 1, z + $[{1\over 2}]$	tetrel	15.89	−10.5	−2.7	−5.0	8.2	−12.4
A⋯D	x + 1, y + $[{1\over 2}]$ , z + $[{3\over 2}]$	C—H⋯O, dispersion	8.93	−10.3	−2.0	−25.3	19.5	−22.4
A⋯E	−x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , z	C—H⋯N	8.73	−10.1	−2.7	−11.7	8.2	−17.8
A⋯F	x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , z	C—H⋯O	8.79	−4.2	−0.5	−20.4	10.8	−15.8
A⋯G	x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1	dispersion	9.56	−4.3	−1.6	−16.0	7.4	−15.1
Note: (a) For details of the interaction modes see Fig. 6. Weak dispersion interaction A⋯G is not shown in the Figure.

Figure 6
The principal pathways of intermolecular interactions, identified with a cut-off limit of 12 kJ mol⁻¹, which involve (a) stacking and tetrel interactions and (a) weak hydrogen bonding. The interaction energies are given in kJ mol⁻¹.

The evaluation of the electrostatic, dispersion and total energy frameworks indicate that the consolidation is dominated via the dispersion energy contributions (Fig. S2 in the supporting information).

6. Database survey

A search of the Cambridge Structural Database (CSD; updated 16 May 2025; Groom et al., 2016 ) reveals 18 relevant hits, which include the 2-oxo-1,2-dihydroquinoline-4-carboxylate core. Two of these entries, namely PEDKAO (Filali Baba et al., 2022) and ROKCIG (Filali Baba et al., 2019), involve additional Cl-atoms installed on the aromatic rings. Oxygen-derivatization of the selected core is a particularly rare feature. Among 13 alkyl-substituted structures retrieved, including AROPAB (Bouzian et al., 2020 ) and SECCAH (Hayani et al., 2021b ), most were identified as N-alkylated derivatives. The only structural precedent for the O-alkylation of the above core is provided by 2-ethoxy-2-oxoethyl 2-(2-ethoxy-2-oxoethoxy)quinoline-4-carboxylate (refcode LIRKIJ; Bouzian et al., 2018). This highlights the need for detailed structural validation when classifying substitution patterns on such frameworks. From a supramolecular perspective, the crystal packing of ROKCIG reveals no π–π stacking interactions or C—H⋯Cl hydrogen bonds, but it differs markedly from that of the title compound. It forms an inversion dimer through C—H⋯O hydrogen bonds, lacking the chain-like hydrogen-bonded pattern seen in the title structure. In contrast, its halogen-free analog (ROKCOM; Filali Baba et al., 2019) forms molecular bands via C—H⋯O hydrogen bonding, further stabilized by weak π–π contacts.

7. Synthesis and crystallization

The procedure for synthesizing the methyl 2-[(4-cyanobenzyl)oxy]quinoline-4-carboxylate derivative is as follows. To a solution of methyl 2-oxo-1,2-dihydroquinoline-4-carboxylate (0.60 g, 2.20 mmol) in 15 ml of dimethylformamide (DMF), 4-(bromomethyl)benzonitrile (0.21 ml, 2.41 mmol), K₂CO₃ (0.85 g, 6.10 mmol) and tetra-n-butylammonium bromide (TBAB; 0.05 g, 0.18 mmol) were added and the reaction mixture was agitated at ambient temperature for a period of 12 h. Following completion of the reaction, the precipitated inorganic salts were removed through filtration and the solvent was evaporated under reduced pressure. The resultant residue was dissolved in dichloromethane. This solution was subsequently dried using anhydrous sodium sulfate and then concentrated under reduced pressure. The compound was purified through column chromatography, employing a hexane/ethyl acetate eluent (4:1 v/v). The target product was obtained in a yield of 45%. It was further recrystallized from a mixture of dichloromethane and hexane (1:4 v/v) giving transparent colorless crystals, m.p. = 394 K. ¹H NMR (300 MHz, CDCl₃), δ, ppm: 8.61 (dd, J = 8.6, 1.4 Hz, 1H, CH_Ar), 7.90–7.86 (m, 1H, CH_Ar), 7.70–7.60 (m, 5H, CH_Ar), 7.53–7.47 (m, 2H, CH_Ar), 5.63 (s, 2H, CH₂), 4.03 (s, 3H, CH₃). ¹³C NMR (75 MHz, CDCl₃), δ, ppm: 166.21, 160.57, 147.34, 142.64, 138.51, 132.40, 130.25, 128.35, 127.85, 125.77, 125.74, 122.1, 118.87, 115.18, 111.74, 66.82, 52.87. FT–IR (cm⁻¹): 2858 (C—H_sp³), 1727 (C=O), 2226 (C≡N), 1575–1607 (C=C, aromatic stretching); 1238 (C—O—C, ether bond).

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. H atoms were positioned geometrically and refined as riding, with C—H = 0.95 Å (aromatic CH), 0.97 Å (CH₂) and 0.98 Å (CH₃) and with U_iso(H) = 1.2U_eq or 1.5U_eq of the carrier C-atom for CH and CH₂ or CH₃ groups, respectively. Four outliers (108, 204, 222 and 232) were omitted in the last cycles of refinement.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₉H₁₄N₂O₃
M_r	318.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	299
a, b, c (Å)	7.7810 (6), 15.6978 (11), 25.966 (2)
V (Å³)	3171.6 (4)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 3 CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.719, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	78015, 3234, 2897
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.136, 1.05
No. of reflections	3234
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.21
Computer programs: APEX4 (Bruker, 2019 ), SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ), DIAMOND (Brandenburg, 1999 ) and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 2465703

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025005547/nu2008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025005547/nu2008Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025005547/nu2008Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2056989025005547/nu2008Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989025005547/nu2008sup5.pdf

checkCIF report

Computing details top

Methyl 2-[(4-cyanophenyl)methoxy]quinoline-4-carboxylate top

Crystal data top

C₁₉H₁₄N₂O₃	D_x = 1.333 Mg m⁻³
M_r = 318.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9947 reflections
a = 7.7810 (6) Å	θ = 3.0–26.1°
b = 15.6978 (11) Å	µ = 0.09 mm⁻¹
c = 25.966 (2) Å	T = 299 K
V = 3171.6 (4) Å³	Prism, colourless
Z = 8	0.26 × 0.22 × 0.19 mm
F(000) = 1328

Data collection top

Bruker D8 VENTURE PHOTON 3 CPAD diffractometer	2897 reflections with I > 2σ(I)
Radiation source: microfocus sealed X-ray tube	R_int = 0.041
φ and ω scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.719, T_max = 0.745	k = −19→17
78015 measured reflections	l = −32→32
3234 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0634P)² + 1.2076P] where P = (F_o² + 2F_c²)/3
3234 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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	0.6069 (3)	0.13417 (10)	0.85140 (5)	0.1081 (8)
O2	0.4881 (2)	0.25179 (9)	0.82571 (5)	0.0777 (5)
O3	0.46253 (17)	0.26146 (7)	0.64306 (4)	0.0539 (3)
N1	0.58631 (19)	0.12898 (8)	0.65387 (5)	0.0472 (3)
N2	0.1671 (3)	0.61040 (12)	0.47079 (7)	0.0908 (7)
C1	0.6466 (2)	0.06874 (9)	0.68811 (6)	0.0434 (4)
C2	0.7132 (3)	−0.00718 (11)	0.66761 (7)	0.0587 (5)
H2	0.7149	−0.0151	0.6321	0.070*
C3	0.7751 (3)	−0.06941 (11)	0.69907 (8)	0.0626 (5)
H3	0.8188	−0.1193	0.6849	0.075*
C4	0.7735 (3)	−0.05892 (11)	0.75228 (8)	0.0573 (4)
H4	0.8159	−0.1018	0.7734	0.069*
C5	0.7101 (2)	0.01379 (10)	0.77346 (6)	0.0490 (4)
H5	0.7105	0.0202	0.8091	0.059*
C6	0.64375 (19)	0.07983 (9)	0.74226 (6)	0.0394 (3)
C7	0.57211 (19)	0.15814 (9)	0.76106 (5)	0.0379 (3)
C8	0.5129 (2)	0.21656 (9)	0.72667 (5)	0.0407 (3)
H8	0.4662	0.2678	0.7380	0.049*
C9	0.5236 (2)	0.19824 (9)	0.67342 (6)	0.0420 (4)
C10	0.5590 (2)	0.17753 (10)	0.81731 (6)	0.0459 (4)
C11	0.4652 (3)	0.27757 (17)	0.87850 (7)	0.0821 (7)
H11A	0.4454	0.3379	0.8799	0.123*
H11B	0.5666	0.2638	0.8979	0.123*
H11C	0.3683	0.2482	0.8929	0.123*
C12	0.4609 (3)	0.24802 (11)	0.58871 (6)	0.0529 (4)
H12A	0.3873	0.2002	0.5802	0.063*
H12B	0.5761	0.2357	0.5765	0.063*
C13	0.3942 (2)	0.32785 (10)	0.56377 (6)	0.0455 (4)
C14	0.3756 (3)	0.40331 (11)	0.59018 (6)	0.0630 (5)
H14	0.4035	0.4054	0.6250	0.076*
C15	0.3163 (3)	0.47576 (11)	0.56604 (7)	0.0668 (6)
H15	0.3036	0.5261	0.5845	0.080*
C16	0.2760 (3)	0.47327 (10)	0.51442 (6)	0.0531 (4)
C17	0.2941 (3)	0.39821 (11)	0.48727 (7)	0.0680 (6)
H17	0.2664	0.3962	0.4525	0.082*
C18	0.3534 (3)	0.32634 (11)	0.51194 (6)	0.0630 (5)
H18	0.3663	0.2760	0.4935	0.076*
C19	0.2146 (3)	0.54952 (12)	0.48955 (7)	0.0663 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.207 (2)	0.0747 (10)	0.0423 (7)	0.0505 (12)	−0.0176 (10)	0.0059 (7)
O2	0.1235 (13)	0.0744 (9)	0.0352 (6)	0.0408 (9)	0.0013 (7)	−0.0046 (6)
O3	0.0886 (9)	0.0396 (6)	0.0336 (6)	0.0134 (6)	−0.0052 (6)	0.0023 (4)
N1	0.0644 (8)	0.0390 (7)	0.0384 (7)	0.0040 (6)	−0.0002 (6)	0.0014 (5)
N2	0.148 (2)	0.0554 (10)	0.0691 (11)	0.0207 (11)	−0.0237 (12)	0.0127 (9)
C1	0.0493 (8)	0.0364 (7)	0.0445 (8)	0.0001 (6)	0.0009 (7)	0.0025 (6)
C2	0.0774 (12)	0.0459 (9)	0.0529 (10)	0.0109 (9)	0.0050 (9)	−0.0033 (7)
C3	0.0752 (13)	0.0415 (9)	0.0710 (12)	0.0152 (9)	0.0028 (10)	−0.0019 (8)
C4	0.0602 (10)	0.0420 (9)	0.0697 (11)	0.0072 (8)	−0.0049 (9)	0.0116 (8)
C5	0.0531 (9)	0.0437 (8)	0.0501 (9)	−0.0003 (7)	−0.0043 (7)	0.0093 (7)
C6	0.0395 (8)	0.0354 (7)	0.0433 (8)	−0.0045 (6)	−0.0002 (6)	0.0042 (6)
C7	0.0398 (7)	0.0367 (7)	0.0373 (7)	−0.0051 (6)	−0.0001 (6)	0.0037 (6)
C8	0.0505 (9)	0.0338 (7)	0.0376 (8)	0.0005 (6)	0.0011 (6)	0.0007 (6)
C9	0.0530 (9)	0.0353 (7)	0.0376 (8)	0.0009 (6)	−0.0015 (6)	0.0042 (6)
C10	0.0553 (9)	0.0444 (8)	0.0380 (8)	−0.0031 (7)	−0.0015 (7)	0.0048 (6)
C11	0.1124 (18)	0.0963 (16)	0.0377 (10)	0.0283 (14)	0.0028 (11)	−0.0135 (10)
C12	0.0792 (12)	0.0454 (8)	0.0341 (8)	0.0106 (8)	−0.0042 (8)	−0.0011 (6)
C13	0.0622 (10)	0.0387 (8)	0.0357 (7)	0.0012 (7)	−0.0037 (7)	0.0008 (6)
C14	0.1068 (16)	0.0476 (9)	0.0347 (8)	0.0127 (10)	−0.0189 (9)	−0.0046 (7)
C15	0.1149 (17)	0.0423 (9)	0.0432 (9)	0.0134 (10)	−0.0172 (10)	−0.0075 (7)
C16	0.0788 (12)	0.0389 (8)	0.0416 (8)	0.0011 (8)	−0.0119 (8)	0.0033 (6)
C17	0.1211 (18)	0.0473 (9)	0.0356 (8)	0.0025 (10)	−0.0210 (10)	0.0000 (7)
C18	0.1131 (16)	0.0393 (8)	0.0366 (8)	0.0046 (9)	−0.0112 (9)	−0.0049 (7)
C19	0.1043 (16)	0.0469 (10)	0.0476 (9)	0.0043 (10)	−0.0163 (10)	0.0023 (8)

Geometric parameters (Å, º) top

O1—C10	1.177 (2)	C7—C10	1.496 (2)
O2—C10	1.308 (2)	C8—C9	1.415 (2)
O2—C11	1.440 (2)	C8—H8	0.9300
O3—C9	1.3535 (18)	C11—H11A	0.9600
O3—C12	1.4269 (18)	C11—H11B	0.9600
N1—C9	1.296 (2)	C11—H11C	0.9600
N1—C1	1.380 (2)	C12—C13	1.503 (2)
N2—C19	1.135 (2)	C12—H12A	0.9700
C1—C2	1.404 (2)	C12—H12B	0.9700
C1—C6	1.417 (2)	C13—C14	1.376 (2)
C2—C3	1.362 (2)	C13—C18	1.383 (2)
C2—H2	0.9300	C14—C15	1.378 (2)
C3—C4	1.391 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.377 (2)
C4—C5	1.360 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.380 (2)
C5—C6	1.413 (2)	C16—C19	1.442 (2)
C5—H5	0.9300	C17—C18	1.377 (2)
C6—C7	1.435 (2)	C17—H17	0.9300
C7—C8	1.360 (2)	C18—H18	0.9300

C10—O2—C11	117.47 (15)	O2—C10—C7	111.91 (13)
C9—O3—C12	118.09 (12)	O2—C11—H11A	109.5
C9—N1—C1	116.79 (13)	O2—C11—H11B	109.5
N1—C1—C2	117.56 (14)	H11A—C11—H11B	109.5
N1—C1—C6	123.34 (14)	O2—C11—H11C	109.5
C2—C1—C6	119.09 (14)	H11A—C11—H11C	109.5
C3—C2—C1	120.79 (16)	H11B—C11—H11C	109.5
C3—C2—H2	119.6	O3—C12—C13	107.82 (13)
C1—C2—H2	119.6	O3—C12—H12A	110.1
C2—C3—C4	120.51 (16)	C13—C12—H12A	110.1
C2—C3—H3	119.7	O3—C12—H12B	110.1
C4—C3—H3	119.7	C13—C12—H12B	110.1
C5—C4—C3	120.29 (16)	H12A—C12—H12B	108.5
C5—C4—H4	119.9	C14—C13—C18	118.39 (15)
C3—C4—H4	119.9	C14—C13—C12	122.62 (14)
C4—C5—C6	121.09 (16)	C18—C13—C12	118.97 (14)
C4—C5—H5	119.5	C13—C14—C15	121.25 (15)
C6—C5—H5	119.5	C13—C14—H14	119.4
C5—C6—C1	118.22 (14)	C15—C14—H14	119.4
C5—C6—C7	125.11 (14)	C16—C15—C14	119.71 (16)
C1—C6—C7	116.66 (13)	C16—C15—H15	120.1
C8—C7—C6	119.06 (13)	C14—C15—H15	120.1
C8—C7—C10	118.73 (13)	C15—C16—C17	119.87 (15)
C6—C7—C10	122.21 (13)	C15—C16—C19	119.21 (15)
C7—C8—C9	118.99 (14)	C17—C16—C19	120.92 (14)
C7—C8—H8	120.5	C18—C17—C16	119.73 (15)
C9—C8—H8	120.5	C18—C17—H17	120.1
N1—C9—O3	121.28 (14)	C16—C17—H17	120.1
N1—C9—C8	125.15 (14)	C17—C18—C13	121.04 (15)
O3—C9—C8	113.57 (13)	C17—C18—H18	119.5
O1—C10—O2	121.57 (16)	C13—C18—H18	119.5
O1—C10—C7	126.52 (16)	N2—C19—C16	178.7 (2)

C9—N1—C1—C2	179.24 (16)	C12—O3—C9—C8	−177.52 (15)
C9—N1—C1—C6	−0.5 (2)	C7—C8—C9—N1	0.0 (3)
N1—C1—C2—C3	179.93 (18)	C7—C8—C9—O3	−179.29 (14)
C6—C1—C2—C3	−0.3 (3)	C11—O2—C10—O1	−2.1 (3)
C1—C2—C3—C4	0.1 (3)	C11—O2—C10—C7	178.98 (18)
C2—C3—C4—C5	−0.1 (3)	C8—C7—C10—O1	−178.7 (2)
C3—C4—C5—C6	0.4 (3)	C6—C7—C10—O1	1.8 (3)
C4—C5—C6—C1	−0.7 (2)	C8—C7—C10—O2	0.2 (2)
C4—C5—C6—C7	179.06 (16)	C6—C7—C10—O2	−179.31 (15)
N1—C1—C6—C5	−179.64 (15)	C9—O3—C12—C13	−177.94 (14)
C2—C1—C6—C5	0.6 (2)	O3—C12—C13—C14	12.1 (3)
N1—C1—C6—C7	0.6 (2)	O3—C12—C13—C18	−169.42 (18)
C2—C1—C6—C7	−179.15 (15)	C18—C13—C14—C15	0.6 (3)
C5—C6—C7—C8	179.86 (15)	C12—C13—C14—C15	179.1 (2)
C1—C6—C7—C8	−0.4 (2)	C13—C14—C15—C16	−0.5 (4)
C5—C6—C7—C10	−0.6 (2)	C14—C15—C16—C17	0.4 (4)
C1—C6—C7—C10	179.15 (14)	C14—C15—C16—C19	−179.9 (2)
C6—C7—C8—C9	0.1 (2)	C15—C16—C17—C18	−0.4 (4)
C10—C7—C8—C9	−179.43 (14)	C19—C16—C17—C18	179.9 (2)
C1—N1—C9—O3	179.42 (14)	C16—C17—C18—C13	0.5 (4)
C1—N1—C9—C8	0.2 (2)	C14—C13—C18—C17	−0.6 (3)
C12—O3—C9—N1	3.2 (2)	C12—C13—C18—C17	−179.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.75	3.651 (2)	163
C5—H5···O1	0.93	2.25	2.883 (2)	125
C15—H15···O1ⁱⁱ	0.93	2.48	3.337 (2)	154
C18—H18···N2ⁱⁱⁱ	0.93	2.68	3.558 (3)	158

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

Calculated interaction energies (kJ mol^-1) top

Interaction energies were calculated employing the CE-B3LYP/6-31G(d,p) functional/basis set combination. The scale factors used to determine E_tot are k_ele = 1.057, k_pol = 0.740, k_dis = 0.871, and k_rep = 0.618 (Mackenzie et al., 2017). R is the distance between the centroids of the interacting molecules.

Path	Symmetry code	Type^a	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
A···B	x + 1/2, y, -z + 3/2	stacking	5.77	-5.3	-2.1	-66.2	30.8	-45.8
A···C	-x + 1, -y + 1, -z + 1	stacking	12.05	-6.1	-2.4	-25.1	9.3	-24.3
B···C	-x + 1/2, -y + 1, z + 1/2	tetrel	15.89	-10.5	-2.7	-5.0	8.2	-12.4
A···D	x + 1, y + 1/2, z + 3/2	C—H···O, dispersion	8.93	-10.3	-2.0	-25.3	19.5	-22.4
A···E	-x + 1/2, y + 1/2, z	C—H···N	8.73	-10.1	-2.7	-11.7	8.2	-17.8
A···F	x + 3/2, yy - 1/2, z	C—H···O	8.79	-4.2	-0.5	-20.4	10.8	-15.8
A···G	x + 1/2, -y + 1/2, -z + 1	dispersion	9.56	-4.3	-1.6	-16.0	7.4	-15.1

Note: (a) For details of the interaction modes see Fig. 7. Weak dispersion interaction A···G is not shown in the Figure.

Acknowledgements

TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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