The crystal structures of two 2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide derivatives are described and the intermolecular contacts in the crystals analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.
Keywords: crystal structure, chromen, piperazine, acetamide, pyran, hydrogen bonding, C—H⋯π interactions, offset π–π interactions, Hirshfeld surface analysis
Abstract
The title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide, C17H19N3O5, (I), and N-(2,4-dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide, C20H19NO6, (II), are new coumarin derivatives. In compound (I), the six-membered piperazine adopts a chair conformation. The dihedral angles between the mean planes of the chromene ring and amide plane is 82.65 (7)° in (I) and 26.2 (4)° in (II). The dihedral angles between the mean planes of the chromene ring and the four planar C atoms of the piperazine ring in (I) and the benzene ring in (II) are 87.66 (6) and 65.0 (4)°, respectively. There are short intramolecular contacts in both molecules forming S(5) ring motifs, viz. N—H⋯N and C—H⋯O in (I), and N—H⋯O and C—H⋯N in (II). In the crystals of both compounds, molecules are linked by N—H⋯O hydrogen bonds, forming chains along [1
0] in (I) and [010] in (II). The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane in the crystals of both compounds. In the crystal of (I), there are also C—H⋯π and offset π–π interactions [intercentroid distance = 3.691 (1) Å] present within the layers. In the crystal of (II), there are only weak offset π–π interactions [intercentroid distance = 3.981 (6) Å] present within the layers. The intermolecular contacts in the crystals of both compounds have been analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.
Chemical context
Coumarin and its derivatives represent one of the most active classes of compounds possessing a wide spectrum of biological activity. The synthesis, and pharmacological and other properties of coumarin derivatives have been studied and reviewed (Kumar et al., 2015 ▸; Kubrak et al., 2017 ▸; Srikrishna et al., 2018 ▸; Venugopala et al., 2013 ▸). Many of these compounds have proven to be active as antibacterial, antifungal, anti-inflammatory, anticoagulant, anti-HIV and antitumor agents. One of the title compounds, 2-(4-{2-[(2-oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I), has been shown to exhibit antimicrobial as well as antioxidant activity (Govindhan, Subramanian, Chennakesava Rao et al., 2015 ▸; Govindhan, Subramanian, Sridharan et al., 2015 ▸). In view of the importance of their natural occurrence, biological activities, pharmacological and medicinal activities, and utility as synthetic intermediates, we have synthesized the title 2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide derivatives, and report herein their crystal structures and Hirshfeld surface analysis.
Structural commentary
The molecular structures of compounds (I) and (II) are illustrated in Figs. 1 ▸ and 2 ▸, respectively. In (I), the piperazine ring (N1/N2/C12–C15) is attached to the 2-[(2-oxochroman-4-yl)oxy]acetaldehyde moiety on atom N1 and to an acetamide moiety on atom N2. It has a chair conformation [puckering parameters: total amplitude Q = 0.561 (2) Å, θ = 0.67 (2)° and φ = 149 (2)°], and is positioned anti with respect to the C—N rotamer of the amide. Nevertheless, because the asymmetry of the chromene residue, the anti conformation can assume a cis or trans geometry with respect to the relative position of the carbonyl O atom of the carboxamide and the C10—C11 and C16—C17 bonds. Both compounds exhibit a cis relation between these bonds, as can be seen in Figs. 1 ▸ and 2 ▸. This molecular conformation permits the formation of intramolecular hydrogen bonds (Tables 1 ▸ and 2 ▸), which enhance the relative planarity of each compound. Specifically for each compound, as a result of the presence of the imidic nitrogen atom, the molecules display intramolecular N—H⋯N and N—H⋯O hydrogen bonds, between the amide nitrogen and the nitrogen atom N2 of the piperazine ring for compound (I), and oxygen atom O3 for (II), forming S(5) ring motifs. In addition, the carbonyl oxygen atom O4 acts as the acceptor for a weak interaction with a hydrogen bond of the exocyclic piperazine ring, forming a second S(5) ring motif in (I), and the amide nitrogen atom N1 acts as the acceptor for a weak interaction with a hydrogen bond of the exocyclic benzene ring, forming a second S(5) ring motif in (II).
Figure 1.
The molecular structure of compound (I), with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular contacts (Table 1 ▸) are shown as dashed lines.
Figure 2.
The molecular structure of compound (II), with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Intramolecular contacts (Table 2 ▸) are shown as dashed lines.
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
Cg1 is the centroid of the C1–C6 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N3—H3B⋯N2 | 0.86 | 2.41 | 2.7716 (15) | 106 |
| C12—H12A⋯O4 | 0.97 | 2.35 | 2.7473 (15) | 104 |
| N3—H3A⋯O4i | 0.86 | 2.05 | 2.8886 (15) | 166 |
| C8—H8⋯O2ii | 0.93 | 2.56 | 3.3953 (16) | 150 |
| C10—H10A⋯O5iii | 0.97 | 2.49 | 3.4506 (18) | 173 |
| C10—H10B⋯O2ii | 0.97 | 2.42 | 3.3346 (16) | 157 |
| C14—H14A⋯O2ii | 0.97 | 2.54 | 3.4012 (17) | 148 |
| C14—H14B⋯Cg1i | 0.97 | 2.80 | 3.614 (2) | 142 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N1—H1⋯O3 | 0.86 | 2.31 | 2.669 (2) | 105 |
| C14—H14⋯N1 | 0.93 | 2.59 | 2.923 (2) | 101 |
| N1—H1⋯O4i | 0.86 | 2.09 | 2.900 (2) | 156 |
| C3—H3⋯O5ii | 0.93 | 2.49 | 3.419 (2) | 175 |
| C5—H5⋯O4i | 0.93 | 2.43 | 3.307 (2) | 157 |
| C15—H15⋯O4iii | 0.93 | 2.51 | 3.399 (2) | 160 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
The values of the dihedral angles between the mean planes of the planar chromene ring system (O1/C1–C9; r.m.s. deviations = 0.008 Å for both compounds) and the amide plane (C10/C11/O4/N1) are 82.65 (7) and 26.2 (4)° in compounds (I) and (II), respectively. In (I), the dihedral angle between the mean planes of the chromene ring and the four C atoms (C12–C15) of the piperazine ring is 87.66 (6)°, while in (II) the benzene ring (C13–C18) is inclined to the mean plane of the chromene ring by 65.0 (4)°. Atom O2 deviates from the coumarin ring mean plane by 0.051 (1) Å in (I) and −0.043 (9) Å in (II).
It is interesting to compare the intramolecular hydrogen bonding present in the title compounds with that of the analogous 4-oxo-N-(substituted phenyl)-4H-chromene-2-carboxamides (Reis et al., 2013 ▸; Gomes et al., 2013 ▸). It can be seen that the effect of the 2/3 positional isomerism is to ‘reflect’ their relative positions while the effect of the cis/trans conformations is a ‘twofold rotation’ of the rings around the Camide—Cchromene bond. These particular differences in conformation may condition the ability for docking when pharmacological activities are considered.
Supramolecular features
In the crystal of (I), molecules are linked by N3—H3A⋯O4i hydrogen bonds, forming chains along the [10] direction, see Fig. 3 ▸ and Table 1 ▸. The chains are linked by C—H⋯O hydrogen bonds, forming layers lying parallel to the ab plane (Fig. 3 ▸ and Table 1 ▸). The C14—H14A⋯O2ii hydrogen bond generates an inversion dimer with an 
(22) ring motif; within the ring C8—H8⋯O2ii and C10—H10B⋯O2ii hydrogen bonds link the molecules into (8) and (14) rings, respectively. These rings are linked by C(10) and C(7) chains formed via the C10—H10A⋯O5iii and N3—H3A⋯O4i hydrogen bonds, respectively. A C—H⋯π interaction is also present within the layer (Table 1 ▸). An offset π–π contact between inversion-related chromene rings further stabilizes the crystal structure [Cg2⋯Cg2iv = 3.691 (1) Å, interplanar distance = 3.490 (1) Å, offset = 1.20 Å; Cg2 is the centroid of the O1/C1–C9 ring; symmetry code: (iv) −x + 1, −y + 1, −z + 1].
Figure 3.
A view along the c axis of the crystal packing of compound (I). The hydrogen bonds (Table 1 ▸) are shown as dashed lines, and H atoms not involved in hydrogen bonding have been omitted.
In the crystal of (II), molecules are linked by N1—H1⋯O4i hydrogen bonds, forming chains along the [010] direction, see Fig. 4 ▸ and Table 2 ▸. The chains are linked by C3—H3⋯O5ii, C5—H5⋯O4i and C15—H15⋯O4iii hydrogen bonds, forming layers parallel to the ab plane (Fig. 4 ▸ and Table 2 ▸). Within the layer there are no C—H⋯π interactions present, only weak offset π–π interactions involving the benzene ring of the chromene ring system and the dimethoxybenzene ring [Cg2⋯Cg3iv = 3.981 (6) Å, interplanar distances = 3.638 (4) and 3.508 (4) Å, offset 0 1.88 Å; Cg2 and Cg3 are the centroids of rings C1–C6 and C13–C18, respectively; symmetry code: (iv) −x + 1, y + 
, −z + 1].
Figure 4.
A view along the a axis of the crystal packing of compound (II). The hydrogen bonds (Table 2 ▸) are shown as dashed lines, and H atoms not involved in hydrogen bonding have been omitted.
Hirshfeld surface analysis
A recent article by Tiekink and collaborators (Tan et al., 2019 ▸) reviews and describes the uses and utility of Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸), and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸), to analyse intermolecular contacts in crystals. The various calculations were performed with CrystalExplorer17 (Turner et al., 2017 ▸).
The Hirshfeld surfaces of compounds (I) and (II) mapped over d norm are given in Fig. 5 ▸, and the intermolecular contacts are illustrated in Fig. 6 ▸ for (I) and Fig. 7 ▸ for (II). They are colour-mapped with the normalized contact distance, d norm, from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The d norm surface was mapped over a fixed colour scale of −0.544 (red) to 1.418 (blue) for compound (I) and −0.501 (red) to 1.672 (blue) for compound (II), where the red spots indicate the intermolecular contacts involved in the hydrogen bonding.
Figure 5.
The Hirshfeld surfaces of compounds (a) (I) and (b) (II), mapped over d norm
Figure 6.
A view of the Hirshfeld surface mapped over d norm of compound (I), showing the various intermolecular contacts in the crystal.
Figure 7.
A view of the Hirshfeld surface mapped over d norm of compound (II), showing the various intermolecular contacts in the crystal.
The fingerprint plots are given in Figs. 8 ▸ and 9 ▸. For compound (I), they reveal that the principal intermolecular contacts are H⋯H at 41.3% (Fig. 8 ▸ b) and O⋯H/H⋯O at 35.3% (Fig. 8 ▸ c), followed by the C⋯H/H⋯C contacts at 11.8% (Fig. 8 ▸ d). For compound (II), they reveal a similar trend, with the principal intermolecular contacts being H⋯H at 41.8% (Fig. 9 ▸ b) and O⋯H/H⋯O at 32.4% (Fig. 9 ▸ c), followed by the C⋯H/H⋯C contacts at 16.7% (Fig. 9 ▸ d). In both compounds, the H⋯H intermolecular contacts predominate, followed by the O⋯H/H⋯O contacts. However the C⋯H/H⋯C contacts are significantly different 11.8% cf. 16.7% for (I) and (II), respectively.
Figure 8.
The full two-dimensional fingerprint plot for compound (I), and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C, (e) C⋯C and (f) N⋯H/H⋯N contacts.
Figure 9.
The full two-dimensional fingerprint plot for compound (II), and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯·H/H⋯C, (e) C⋯C and (f) N⋯H/H⋯N contacts.
Database survey
A search of the Cambridge Structural Database (CSD, V5.40, update February 2019; Groom et al., 2016 ▸) for 2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide derivatives gave two hits. They include 2-[(2-oxo-2H-chromen-4-yl)oxy]-N-(1-phenylethyl)acetamide (CSD refcode PUWMEB; Govindhan, Subramanian, Chennakesava Rao et al., 2015 ▸) and N-(3,5-dimethyladamantan-1-yl)-2-[(2-oxo-2H-chromen-4-yl)oxy]propanamide (SEFRAY; Rambabu et al., 2012 ▸).
A search for linear and angular pyranocoumarin (psoralene class) structures gave 35 hits. They include four reports, CSD refcodes AMYROL [Kato, 1970 ▸: seselin (smyrolin)]; AMYROL01 [Bauri et al., 2006 ▸; seselin (redetermination)]; FUGVOS [Thailambal & Pattabhi, 1987 ▸: 2,3-dihydroxy-9-hydroxy-2(1-hydroxy-1-methylethyl)-7H-furo-[3,2-g]-[1]-benzopyran-7-one; bromohydroxyseselin (Bauri et al., 2017a ▸); dibromomomethoxyseselin (DMS) (Bauri et al., 2017b ▸)], and a number of structures with various substituents at C3 and C4, many of which are natural products.
A CSD search found five coumarin ester structures with substituents at the 7 position (Ramasubbu et al., 1982 ▸; Gnanaguru et al., 1985 ▸; Parveen et al., 2011 ▸; Zhuo et al., 2014 ▸; Ji et al., 2017 ▸). In these structures and those of meta-substituted coumarin esters (Abou et al., 2012 ▸, 2013 ▸; Bibila Mayaya Bisseyou et al., 2013 ▸; Zhang et al., 2014 ▸; Gomes et al., 2016 ▸; Ziki et al., 2016 ▸, 2017 ▸), the pyrone rings all show three long (in the range 1.37–1.46 Å) and one short (1.32–1.34 Å) C—C distances, suggesting that the electronic density is preferentially located in the short C—C bond at the pyrone ring. This pattern is clearly repeated here with C1—C6 = 1.3883 (18) and 1.394 (11) Å, C6—C7 = 1.4538 (15) and 1.398 (12) Å, C7—C8 = 1.3444 (17) and 1.352 (12) Å and C8—C9 = 1.4338 (18) and 1.433 (12) Å.
Intramolecular C—H⋯O short contacts similar to that observed in the title compounds were found in five compounds in the CSD: LISLAB, 1-(1-pyrrolidinylcarbonyl)cyclopropyl sulfamate (Morin et al., 2007 ▸), PEQHAU, 2-[30-(400-chlorophenyl)-40,60-dimethoxyindol-70-yl]glyoxyl-1-pyrrolidine (Black et al., 1997 ▸), QIBBEJ, [2-hydroxy-5-(2-hydroxybenzoyl)phenyl](pyrrolidin-1-yl)-methanone (Holtz et al., 2007 ▸), SINHAZ, 2-methoxy-1-(1-pyrrolidinylcarbonyl)naphthalene (Sakamoto et al., 2007 ▸) and TAJDIR, (4S,5S)-4,5-bispyrrolidinylcarbonyl)-2,2-dimethyl-1,3-dioxolane (Garcia et al., 1991 ▸).
Synthesis and crystallization
Compound (I) To a solution of 1 equiv. of 4-(2-(piperazine-1-yl)ethoxy)-2H-chromen-2-one (1.0 g) in dichloromethane (10 ml) at 273–278 K were added triethylamine (0.7 g, 2.0 equiv.) followed by iodoacetamide (1.0 g, 0.5 equiv.), and the reaction mixture was stirred at the same temperature for 1 h. On completion of the reaction (monitored by TLC), the reaction mixture was diluted with dichloromethane and water (10 ml). The organic layer was separated and washed with brine solution. It was then dried over anhydrous sodium sulfate, filtered and then evaporated under reduced pressure giving compound (I) as a white solid, which was then washed with hexane and dried under vacuum. Colourless block-like crystals of compound (I) were obtained by slow evaporation of a solution in chloroform (4 ml) and methanol (1 ml).
Compound (II) N,N-Diisopropylethylamine (DIPEA; 1.82 g, 3.1 equiv.) was added to a mixture of 2-(2-oxo-2H-chromen-4-yloxy)acetic acid (1.0 g, 1.0 equiv.), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI; 1.0 g, 1.2 equiv.), 1-hydroxybenzotriazole hydrate (HOBt; 0.61 g, 1.0 equiv.), 2,4-dimethoxybenzylamine (0.8 g, 1.0 equiv.) in N,N-dimethylformamide (5 ml) at 273–278 K. The temperature of the mixture was raised to ambient temperature and stirred for 8 h. Progress of the reaction was monitored by TLC (mobile phase: ethyl acetate/hexane). After completion of the reaction, the mixture was poured into ice–water and compound (II) was obtained as a white solid. It was then filtered, washed with hexane and dried under vacuum. Colourless block-like crystals of compound (II) were obtained by slow evaporation of a solution in chloroform (5 ml).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. For both compounds the H atoms were positioned geometrically and constrained to ride on their parent atoms: N—H = 0.86 Å and C–H = 0.93—0.97Å with U iso(H) = 1.5U eq(C-methyl) and 1.2U eq(N, C) for other H atoms.
Table 3. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C17H19N3O5 | C20H19NO6 |
| M r | 345.35 | 369.36 |
| Crystal system, space group | Triclinic, P
|
Monoclinic, P21 |
| Temperature (K) | 293 | 296 |
| a, b, c (Å) | 8.5260 (3), 8.8415 (3), 11.9462 (4) | 7.2779 (2), 8.5759 (3), 14.4099 (5) |
| α, β, γ (°) | 88.660 (2), 69.568 (2), 70.724 (2) | 90, 93.796 (5), 90 |
| V (Å3) | 792.27 (5) | 897.41 (5) |
| Z | 2 | 2 |
| Radiation type | Mo Kα | Mo Kα |
| μ (mm−1) | 0.11 | 0.10 |
| Crystal size (mm) | 0.25 × 0.24 × 0.20 | 0.30 × 0.25 × 0.20 |
| Data collection | ||
| Diffractometer | Bruker Kappa APEXII CCD | Bruker Kappa APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2008 ▸) | Multi-scan (SADABS; Bruker, 2008 ▸) |
| T min, T max | 0.756, 0.824 | 0.763, 0.852 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 12022, 3382, 2947 | 4058, 2630, 1623 |
| R int | 0.027 | 0.088 |
| (sin θ/λ)max (Å−1) | 0.637 | 0.595 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.039, 0.110, 1.04 | 0.083, 0.243, 0.98 |
| No. of reflections | 3382 | 2630 |
| No. of parameters | 227 | 247 |
| No. of restraints | 0 | 1 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.30, −0.18 | 0.28, −0.29 |
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989019003736/su5482sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019003736/su5482Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989019003736/su5482IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989019003736/su5482Isup4.cml
Supporting information file. DOI: 10.1107/S2056989019003736/su5482IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the SAIF, IIT Madras, for the data collection.
supplementary crystallographic information
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Crystal data
| C17H19N3O5 | Z = 2 |
| Mr = 345.35 | F(000) = 364 |
| Triclinic, P1 | Dx = 1.448 Mg m−3 |
| a = 8.5260 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.8415 (3) Å | Cell parameters from 3382 reflections |
| c = 11.9462 (4) Å | θ = 1.8–26.9° |
| α = 88.660 (2)° | µ = 0.11 mm−1 |
| β = 69.568 (2)° | T = 293 K |
| γ = 70.724 (2)° | Block, colourless |
| V = 792.27 (5) Å3 | 0.25 × 0.24 × 0.20 mm |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Data collection
| Bruker Kappa APEXII CCD diffractometer | 2947 reflections with I > 2σ(I) |
| ω and φ scans | Rint = 0.027 |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.9°, θmin = 1.8° |
| Tmin = 0.756, Tmax = 0.824 | h = −10→10 |
| 12022 measured reflections | k = −11→11 |
| 3382 independent reflections | l = −15→15 |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.2007P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3382 reflections | Δρmax = 0.30 e Å−3 |
| 227 parameters | Δρmin = −0.18 e Å−3 |
| 0 restraints | Extinction correction: (SHELXL2018; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (4) |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Special details
| 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. |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.57138 (16) | 0.24849 (15) | 0.44898 (11) | 0.0326 (3) | |
| C2 | 0.72086 (18) | 0.15454 (16) | 0.47279 (13) | 0.0396 (3) | |
| H2 | 0.713439 | 0.076848 | 0.526334 | 0.047* | |
| C3 | 0.87983 (18) | 0.17916 (17) | 0.41538 (13) | 0.0426 (3) | |
| H3 | 0.980829 | 0.116794 | 0.430161 | 0.051* | |
| C4 | 0.89217 (18) | 0.29534 (18) | 0.33584 (13) | 0.0419 (3) | |
| H4 | 1.000730 | 0.310220 | 0.297651 | 0.050* | |
| C5 | 0.74271 (16) | 0.38890 (16) | 0.31349 (12) | 0.0355 (3) | |
| H5 | 0.750512 | 0.467720 | 0.260957 | 0.043* | |
| C6 | 0.57975 (15) | 0.36540 (14) | 0.36965 (11) | 0.0297 (3) | |
| C7 | 0.41622 (16) | 0.45736 (14) | 0.35108 (11) | 0.0298 (3) | |
| C8 | 0.26528 (16) | 0.42648 (15) | 0.40841 (12) | 0.0359 (3) | |
| H8 | 0.162437 | 0.483635 | 0.393790 | 0.043* | |
| C9 | 0.25981 (17) | 0.30714 (16) | 0.49166 (13) | 0.0385 (3) | |
| C10 | 0.28057 (16) | 0.68340 (15) | 0.26066 (12) | 0.0328 (3) | |
| H10A | 0.295441 | 0.787474 | 0.249025 | 0.039* | |
| H10B | 0.176835 | 0.696178 | 0.332561 | 0.039* | |
| C11 | 0.25178 (15) | 0.62523 (14) | 0.15331 (11) | 0.0316 (3) | |
| C12 | 0.11451 (17) | 0.69477 (15) | 0.00279 (11) | 0.0342 (3) | |
| H12A | 0.191175 | 0.585566 | −0.031236 | 0.041* | |
| H12B | 0.137190 | 0.766053 | −0.059147 | 0.041* | |
| C13 | −0.07778 (17) | 0.70594 (14) | 0.04377 (13) | 0.0358 (3) | |
| H13A | −0.104008 | 0.680104 | −0.024677 | 0.043* | |
| H13B | −0.097577 | 0.627835 | 0.100571 | 0.043* | |
| C14 | −0.15445 (17) | 0.91151 (15) | 0.20136 (11) | 0.0349 (3) | |
| H14A | −0.176974 | 0.839746 | 0.262958 | 0.042* | |
| H14B | −0.231186 | 1.020451 | 0.236057 | 0.042* | |
| C15 | 0.03821 (17) | 0.90093 (14) | 0.16159 (12) | 0.0348 (3) | |
| H15A | 0.058654 | 0.980127 | 0.105913 | 0.042* | |
| H15B | 0.064622 | 0.924109 | 0.230622 | 0.042* | |
| C16 | −0.38171 (17) | 0.87031 (15) | 0.14408 (15) | 0.0423 (3) | |
| H16A | −0.401742 | 0.814610 | 0.215885 | 0.051* | |
| H16B | −0.396724 | 0.810638 | 0.083757 | 0.051* | |
| C17 | −0.52246 (17) | 1.03707 (16) | 0.17290 (14) | 0.0419 (3) | |
| N1 | 0.15528 (13) | 0.73936 (12) | 0.10337 (9) | 0.0319 (2) | |
| N2 | −0.19807 (13) | 0.86796 (11) | 0.10060 (9) | 0.0308 (2) | |
| N3 | −0.47248 (16) | 1.15212 (14) | 0.11445 (12) | 0.0465 (3) | |
| H3A | −0.547778 | 1.248448 | 0.125737 | 0.056* | |
| H3B | −0.364686 | 1.130611 | 0.065147 | 0.056* | |
| O1 | 0.41560 (12) | 0.22028 (11) | 0.50832 (9) | 0.0416 (2) | |
| O2 | 0.12892 (14) | 0.27595 (14) | 0.55044 (11) | 0.0566 (3) | |
| O3 | 0.43529 (11) | 0.57057 (11) | 0.27551 (9) | 0.0382 (2) | |
| O4 | 0.31673 (15) | 0.48319 (11) | 0.11304 (10) | 0.0529 (3) | |
| O5 | −0.67279 (15) | 1.05727 (14) | 0.24444 (14) | 0.0753 (4) |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0309 (6) | 0.0317 (6) | 0.0322 (6) | −0.0043 (5) | −0.0139 (5) | 0.0023 (5) |
| C2 | 0.0411 (7) | 0.0344 (6) | 0.0401 (7) | −0.0007 (5) | −0.0225 (6) | 0.0044 (5) |
| C3 | 0.0347 (7) | 0.0414 (7) | 0.0480 (8) | 0.0031 (5) | −0.0252 (6) | −0.0034 (6) |
| C4 | 0.0283 (6) | 0.0502 (8) | 0.0437 (8) | −0.0067 (6) | −0.0150 (6) | −0.0027 (6) |
| C5 | 0.0309 (6) | 0.0402 (7) | 0.0330 (7) | −0.0080 (5) | −0.0128 (5) | 0.0042 (5) |
| C6 | 0.0275 (6) | 0.0309 (6) | 0.0280 (6) | −0.0032 (5) | −0.0132 (5) | 0.0006 (5) |
| C7 | 0.0298 (6) | 0.0305 (6) | 0.0285 (6) | −0.0061 (5) | −0.0141 (5) | 0.0057 (5) |
| C8 | 0.0282 (6) | 0.0379 (7) | 0.0415 (7) | −0.0068 (5) | −0.0173 (5) | 0.0110 (5) |
| C9 | 0.0312 (6) | 0.0395 (7) | 0.0431 (7) | −0.0089 (5) | −0.0146 (5) | 0.0109 (6) |
| C10 | 0.0287 (6) | 0.0318 (6) | 0.0394 (7) | −0.0072 (5) | −0.0177 (5) | 0.0130 (5) |
| C11 | 0.0277 (6) | 0.0270 (6) | 0.0371 (7) | −0.0049 (4) | −0.0129 (5) | 0.0088 (5) |
| C12 | 0.0354 (6) | 0.0293 (6) | 0.0328 (6) | −0.0015 (5) | −0.0153 (5) | 0.0001 (5) |
| C13 | 0.0385 (7) | 0.0252 (6) | 0.0436 (7) | −0.0057 (5) | −0.0195 (6) | −0.0003 (5) |
| C14 | 0.0347 (6) | 0.0295 (6) | 0.0336 (7) | −0.0003 (5) | −0.0142 (5) | 0.0009 (5) |
| C15 | 0.0372 (7) | 0.0236 (5) | 0.0443 (7) | −0.0008 (5) | −0.0243 (6) | −0.0003 (5) |
| C16 | 0.0325 (7) | 0.0316 (6) | 0.0635 (9) | −0.0104 (5) | −0.0192 (6) | 0.0099 (6) |
| C17 | 0.0281 (6) | 0.0363 (7) | 0.0591 (9) | −0.0070 (5) | −0.0171 (6) | 0.0049 (6) |
| N1 | 0.0322 (5) | 0.0250 (5) | 0.0363 (6) | −0.0012 (4) | −0.0179 (4) | 0.0017 (4) |
| N2 | 0.0278 (5) | 0.0250 (5) | 0.0388 (6) | −0.0047 (4) | −0.0153 (4) | 0.0032 (4) |
| N3 | 0.0340 (6) | 0.0324 (6) | 0.0650 (8) | −0.0031 (5) | −0.0166 (6) | 0.0110 (5) |
| O1 | 0.0351 (5) | 0.0414 (5) | 0.0469 (6) | −0.0093 (4) | −0.0178 (4) | 0.0197 (4) |
| O2 | 0.0375 (5) | 0.0654 (7) | 0.0673 (7) | −0.0209 (5) | −0.0181 (5) | 0.0328 (6) |
| O3 | 0.0280 (4) | 0.0439 (5) | 0.0448 (5) | −0.0100 (4) | −0.0190 (4) | 0.0205 (4) |
| O4 | 0.0659 (7) | 0.0272 (5) | 0.0597 (7) | 0.0043 (4) | −0.0346 (6) | 0.0017 (4) |
| O5 | 0.0340 (6) | 0.0528 (7) | 0.1128 (11) | −0.0086 (5) | −0.0018 (6) | 0.0128 (7) |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Geometric parameters (Å, º)
| C1—O1 | 1.3718 (16) | C11—N1 | 1.3482 (15) |
| C1—C6 | 1.3883 (18) | C12—N1 | 1.4574 (16) |
| C1—C2 | 1.3922 (17) | C12—C13 | 1.5073 (18) |
| C2—C3 | 1.376 (2) | C12—H12A | 0.9700 |
| C2—H2 | 0.9300 | C12—H12B | 0.9700 |
| C3—C4 | 1.387 (2) | C13—N2 | 1.4677 (15) |
| C3—H3 | 0.9300 | C13—H13A | 0.9700 |
| C4—C5 | 1.3823 (18) | C13—H13B | 0.9700 |
| C4—H4 | 0.9300 | C14—N2 | 1.4712 (16) |
| C5—C6 | 1.3990 (17) | C14—C15 | 1.5127 (18) |
| C5—H5 | 0.9300 | C14—H14A | 0.9700 |
| C6—C7 | 1.4538 (15) | C14—H14B | 0.9700 |
| C7—O3 | 1.3439 (15) | C15—N1 | 1.4632 (15) |
| C7—C8 | 1.3444 (17) | C15—H15A | 0.9700 |
| C8—C9 | 1.4338 (18) | C15—H15B | 0.9700 |
| C8—H8 | 0.9300 | C16—N2 | 1.4604 (16) |
| C9—O2 | 1.2089 (16) | C16—C17 | 1.5164 (18) |
| C9—O1 | 1.3774 (15) | C16—H16A | 0.9700 |
| C10—O3 | 1.4328 (13) | C16—H16B | 0.9700 |
| C10—C11 | 1.5177 (18) | C17—O5 | 1.2232 (18) |
| C10—H10A | 0.9700 | C17—N3 | 1.3226 (19) |
| C10—H10B | 0.9700 | N3—H3A | 0.8600 |
| C11—O4 | 1.2241 (15) | N3—H3B | 0.8600 |
| O1—C1—C6 | 121.80 (11) | C13—C12—H12B | 109.6 |
| O1—C1—C2 | 116.65 (12) | H12A—C12—H12B | 108.1 |
| C6—C1—C2 | 121.54 (12) | N2—C13—C12 | 111.22 (10) |
| C3—C2—C1 | 118.55 (13) | N2—C13—H13A | 109.4 |
| C3—C2—H2 | 120.7 | C12—C13—H13A | 109.4 |
| C1—C2—H2 | 120.7 | N2—C13—H13B | 109.4 |
| C2—C3—C4 | 121.20 (12) | C12—C13—H13B | 109.4 |
| C2—C3—H3 | 119.4 | H13A—C13—H13B | 108.0 |
| C4—C3—H3 | 119.4 | N2—C14—C15 | 111.67 (10) |
| C5—C4—C3 | 119.83 (13) | N2—C14—H14A | 109.3 |
| C5—C4—H4 | 120.1 | C15—C14—H14A | 109.3 |
| C3—C4—H4 | 120.1 | N2—C14—H14B | 109.3 |
| C4—C5—C6 | 120.20 (13) | C15—C14—H14B | 109.3 |
| C4—C5—H5 | 119.9 | H14A—C14—H14B | 107.9 |
| C6—C5—H5 | 119.9 | N1—C15—C14 | 109.84 (10) |
| C1—C6—C5 | 118.66 (11) | N1—C15—H15A | 109.7 |
| C1—C6—C7 | 117.34 (11) | C14—C15—H15A | 109.7 |
| C5—C6—C7 | 123.99 (11) | N1—C15—H15B | 109.7 |
| O3—C7—C8 | 126.49 (11) | C14—C15—H15B | 109.7 |
| O3—C7—C6 | 113.36 (10) | H15A—C15—H15B | 108.2 |
| C8—C7—C6 | 120.14 (11) | N2—C16—C17 | 114.84 (10) |
| C7—C8—C9 | 121.26 (11) | N2—C16—H16A | 108.6 |
| C7—C8—H8 | 119.4 | C17—C16—H16A | 108.6 |
| C9—C8—H8 | 119.4 | N2—C16—H16B | 108.6 |
| O2—C9—O1 | 116.18 (12) | C17—C16—H16B | 108.6 |
| O2—C9—C8 | 125.71 (12) | H16A—C16—H16B | 107.5 |
| O1—C9—C8 | 118.11 (11) | O5—C17—N3 | 124.21 (13) |
| O3—C10—C11 | 110.44 (10) | O5—C17—C16 | 119.73 (13) |
| O3—C10—H10A | 109.6 | N3—C17—C16 | 116.04 (12) |
| C11—C10—H10A | 109.6 | C11—N1—C12 | 120.29 (10) |
| O3—C10—H10B | 109.6 | C11—N1—C15 | 125.01 (11) |
| C11—C10—H10B | 109.6 | C12—N1—C15 | 111.98 (9) |
| H10A—C10—H10B | 108.1 | C16—N2—C13 | 109.10 (10) |
| O4—C11—N1 | 122.28 (12) | C16—N2—C14 | 109.88 (10) |
| O4—C11—C10 | 121.53 (11) | C13—N2—C14 | 109.94 (9) |
| N1—C11—C10 | 116.17 (10) | C17—N3—H3A | 120.0 |
| N1—C12—C13 | 110.40 (10) | C17—N3—H3B | 120.0 |
| N1—C12—H12A | 109.6 | H3A—N3—H3B | 120.0 |
| C13—C12—H12A | 109.6 | C1—O1—C9 | 121.30 (10) |
| N1—C12—H12B | 109.6 | C7—O3—C10 | 119.29 (9) |
| O1—C1—C2—C3 | −179.85 (11) | N2—C16—C17—O5 | −155.82 (15) |
| C6—C1—C2—C3 | −0.22 (19) | N2—C16—C17—N3 | 25.9 (2) |
| C1—C2—C3—C4 | 0.4 (2) | O4—C11—N1—C12 | 4.18 (19) |
| C2—C3—C4—C5 | 0.2 (2) | C10—C11—N1—C12 | −177.62 (10) |
| C3—C4—C5—C6 | −0.8 (2) | O4—C11—N1—C15 | 163.96 (13) |
| O1—C1—C6—C5 | 179.20 (11) | C10—C11—N1—C15 | −17.84 (18) |
| C2—C1—C6—C5 | −0.42 (18) | C13—C12—N1—C11 | 105.42 (13) |
| O1—C1—C6—C7 | −0.25 (18) | C13—C12—N1—C15 | −56.81 (14) |
| C2—C1—C6—C7 | −179.87 (11) | C14—C15—N1—C11 | −105.06 (14) |
| C4—C5—C6—C1 | 0.93 (19) | C14—C15—N1—C12 | 56.17 (14) |
| C4—C5—C6—C7 | −179.66 (12) | C17—C16—N2—C13 | −163.63 (12) |
| C1—C6—C7—O3 | 178.34 (10) | C17—C16—N2—C14 | 75.77 (15) |
| C5—C6—C7—O3 | −1.09 (17) | C12—C13—N2—C16 | −177.13 (11) |
| C1—C6—C7—C8 | −0.84 (18) | C12—C13—N2—C14 | −56.57 (14) |
| C5—C6—C7—C8 | 179.74 (12) | C15—C14—N2—C16 | 176.60 (10) |
| O3—C7—C8—C9 | −176.93 (12) | C15—C14—N2—C13 | 56.50 (13) |
| C6—C7—C8—C9 | 2.1 (2) | C6—C1—O1—C9 | 0.03 (18) |
| C7—C8—C9—O2 | 176.98 (14) | C2—C1—O1—C9 | 179.66 (12) |
| C7—C8—C9—O1 | −2.3 (2) | O2—C9—O1—C1 | −178.15 (12) |
| O3—C10—C11—O4 | 21.02 (17) | C8—C9—O1—C1 | 1.20 (19) |
| O3—C10—C11—N1 | −157.19 (10) | C8—C7—O3—C10 | 6.90 (19) |
| N1—C12—C13—N2 | 56.80 (14) | C6—C7—O3—C10 | −172.21 (10) |
| N2—C14—C15—N1 | −56.02 (13) | C11—C10—O3—C7 | −94.52 (13) |
2-(4-{2-[(2-Oxo-2H-chromen-4-yl)oxy]acetyl}piperazin-1-yl)acetamide (I) . Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C1–C6 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3B···N2 | 0.86 | 2.41 | 2.7716 (15) | 106 |
| C12—H12A···O4 | 0.97 | 2.35 | 2.7473 (15) | 104 |
| N3—H3A···O4i | 0.86 | 2.05 | 2.8886 (15) | 166 |
| C8—H8···O2ii | 0.93 | 2.56 | 3.3953 (16) | 150 |
| C10—H10A···O5iii | 0.97 | 2.49 | 3.4506 (18) | 173 |
| C10—H10B···O2ii | 0.97 | 2.42 | 3.3346 (16) | 157 |
| C14—H14A···O2ii | 0.97 | 2.54 | 3.4012 (17) | 148 |
| C14—H14B···Cg1i | 0.97 | 2.80 | 3.614 (2) | 142 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z.
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Crystal data
| C20H19NO6 | F(000) = 388 |
| Mr = 369.36 | Dx = 1.367 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.2779 (2) Å | Cell parameters from 2630 reflections |
| b = 8.5759 (3) Å | θ = 1.4–25.0° |
| c = 14.4099 (5) Å | µ = 0.10 mm−1 |
| β = 93.796 (5)° | T = 296 K |
| V = 897.41 (5) Å3 | Block, colourless |
| Z = 2 | 0.30 × 0.25 × 0.20 mm |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Data collection
| Bruker Kappa APEXII CCD diffractometer | 1623 reflections with I > 2σ(I) |
| ω and φ scans | Rint = 0.088 |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 1.4° |
| Tmin = 0.763, Tmax = 0.852 | h = −8→8 |
| 4058 measured reflections | k = −9→9 |
| 2630 independent reflections | l = −17→16 |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.083 | H-atom parameters constrained |
| wR(F2) = 0.243 | w = 1/[σ2(Fo2) + (0.1336P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.98 | (Δ/σ)max < 0.001 |
| 2630 reflections | Δρmax = 0.28 e Å−3 |
| 247 parameters | Δρmin = −0.29 e Å−3 |
| 1 restraint | Extinction correction: (SHELXL2018; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.042 (15) |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Special details
| 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. |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C9 | 0.7608 (13) | 0.3941 (14) | 0.8943 (6) | 0.063 (3) | |
| C1 | 0.9935 (12) | 0.5490 (11) | 0.8258 (6) | 0.053 (2) | |
| C2 | 1.1588 (13) | 0.6195 (14) | 0.8397 (7) | 0.064 (3) | |
| H2 | 1.225084 | 0.612966 | 0.897037 | 0.077* | |
| C3 | 1.2277 (13) | 0.7016 (13) | 0.7673 (7) | 0.067 (3) | |
| H3 | 1.340590 | 0.752129 | 0.775680 | 0.080* | |
| C4 | 1.1281 (13) | 0.7085 (14) | 0.6818 (7) | 0.065 (3) | |
| H4 | 1.175985 | 0.762353 | 0.632809 | 0.078* | |
| C5 | 0.9635 (12) | 0.6383 (12) | 0.6689 (6) | 0.056 (3) | |
| H5 | 0.898157 | 0.645409 | 0.611398 | 0.067* | |
| C6 | 0.8876 (11) | 0.5536 (11) | 0.7417 (6) | 0.048 (2) | |
| C7 | 0.7177 (12) | 0.4769 (10) | 0.7354 (5) | 0.047 (2) | |
| C8 | 0.6529 (13) | 0.3977 (13) | 0.8075 (7) | 0.060 (3) | |
| H8 | 0.540283 | 0.346313 | 0.800782 | 0.072* | |
| C10 | 0.4698 (11) | 0.3848 (12) | 0.6345 (6) | 0.052 (2) | |
| H10A | 0.365667 | 0.432162 | 0.662342 | 0.062* | |
| H10B | 0.493567 | 0.284583 | 0.664029 | 0.062* | |
| C11 | 0.4238 (11) | 0.3613 (11) | 0.5313 (6) | 0.046 (2) | |
| C12 | 0.4617 (11) | 0.4368 (12) | 0.3725 (6) | 0.053 (2) | |
| H12A | 0.461193 | 0.326030 | 0.358746 | 0.064* | |
| H12B | 0.563467 | 0.482854 | 0.341984 | 0.064* | |
| C13 | 0.2869 (10) | 0.5056 (10) | 0.3312 (5) | 0.043 (2) | |
| C14 | 0.1620 (12) | 0.5896 (12) | 0.3804 (7) | 0.059 (3) | |
| H14 | 0.190916 | 0.609186 | 0.443136 | 0.071* | |
| C15 | −0.0013 (12) | 0.6448 (14) | 0.3410 (7) | 0.062 (3) | |
| H15 | −0.081969 | 0.699614 | 0.376388 | 0.074* | |
| C16 | −0.0442 (11) | 0.6175 (12) | 0.2473 (6) | 0.052 (2) | |
| C17 | 0.0765 (11) | 0.5380 (11) | 0.1954 (6) | 0.052 (2) | |
| H17 | 0.048794 | 0.523211 | 0.132044 | 0.062* | |
| C18 | 0.2389 (11) | 0.4798 (11) | 0.2368 (6) | 0.048 (2) | |
| C19 | 0.3259 (14) | 0.3671 (17) | 0.0943 (6) | 0.080 (4) | |
| H19A | 0.212442 | 0.310013 | 0.086580 | 0.120* | |
| H19B | 0.423474 | 0.306460 | 0.070819 | 0.120* | |
| H19C | 0.313972 | 0.463616 | 0.060635 | 0.120* | |
| C20 | −0.2598 (13) | 0.6447 (17) | 0.1157 (7) | 0.085 (4) | |
| H20A | −0.162895 | 0.679847 | 0.078717 | 0.127* | |
| H20B | −0.371543 | 0.699158 | 0.097180 | 0.127* | |
| H20C | −0.278034 | 0.534745 | 0.106668 | 0.127* | |
| N1 | 0.4962 (10) | 0.4564 (9) | 0.4721 (5) | 0.051 (2) | |
| H1 | 0.565201 | 0.531787 | 0.492909 | 0.061* | |
| O1 | 0.9285 (9) | 0.4669 (9) | 0.9009 (4) | 0.068 (2) | |
| O2 | 0.7213 (10) | 0.3219 (10) | 0.9634 (5) | 0.084 (3) | |
| O3 | 0.6246 (8) | 0.4805 (7) | 0.6494 (4) | 0.0562 (18) | |
| O4 | 0.3165 (8) | 0.2542 (8) | 0.5078 (4) | 0.0560 (18) | |
| O5 | 0.3671 (8) | 0.3989 (9) | 0.1907 (4) | 0.0641 (19) | |
| O6 | −0.2109 (8) | 0.6749 (9) | 0.2111 (5) | 0.072 (2) |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C9 | 0.079 (6) | 0.082 (8) | 0.028 (5) | −0.001 (6) | −0.004 (4) | −0.001 (5) |
| C1 | 0.074 (6) | 0.060 (6) | 0.025 (5) | 0.007 (5) | −0.004 (4) | 0.000 (4) |
| C2 | 0.065 (6) | 0.087 (9) | 0.039 (5) | −0.006 (6) | −0.009 (4) | 0.004 (6) |
| C3 | 0.063 (6) | 0.079 (8) | 0.056 (7) | −0.010 (6) | −0.011 (5) | 0.002 (6) |
| C4 | 0.073 (6) | 0.080 (8) | 0.042 (6) | −0.006 (6) | 0.002 (4) | 0.007 (6) |
| C5 | 0.057 (5) | 0.066 (7) | 0.042 (5) | −0.008 (5) | −0.008 (4) | 0.009 (5) |
| C6 | 0.053 (5) | 0.058 (6) | 0.029 (5) | −0.002 (4) | −0.007 (4) | 0.001 (4) |
| C7 | 0.071 (5) | 0.049 (6) | 0.018 (4) | 0.002 (5) | −0.008 (4) | 0.003 (4) |
| C8 | 0.068 (6) | 0.075 (7) | 0.036 (5) | −0.007 (5) | −0.003 (4) | 0.004 (5) |
| C10 | 0.059 (5) | 0.065 (7) | 0.031 (5) | −0.012 (5) | −0.007 (4) | 0.003 (5) |
| C11 | 0.057 (5) | 0.046 (5) | 0.033 (5) | −0.004 (5) | −0.007 (4) | 0.004 (5) |
| C12 | 0.056 (5) | 0.063 (6) | 0.040 (5) | 0.000 (5) | −0.002 (4) | −0.006 (5) |
| C13 | 0.049 (4) | 0.048 (6) | 0.032 (4) | −0.003 (4) | 0.001 (3) | 0.001 (4) |
| C14 | 0.059 (5) | 0.072 (7) | 0.048 (6) | 0.006 (5) | 0.000 (4) | −0.006 (5) |
| C15 | 0.063 (5) | 0.077 (7) | 0.046 (5) | 0.012 (5) | 0.007 (4) | −0.021 (6) |
| C16 | 0.043 (4) | 0.073 (7) | 0.041 (5) | 0.011 (5) | 0.005 (4) | 0.001 (5) |
| C17 | 0.055 (5) | 0.066 (6) | 0.035 (5) | 0.011 (5) | 0.000 (4) | −0.001 (5) |
| C18 | 0.049 (4) | 0.053 (6) | 0.042 (5) | 0.004 (4) | 0.009 (4) | −0.003 (5) |
| C19 | 0.082 (7) | 0.130 (11) | 0.029 (5) | 0.008 (7) | 0.005 (4) | −0.006 (7) |
| C20 | 0.067 (6) | 0.137 (11) | 0.048 (6) | 0.033 (7) | −0.012 (5) | −0.014 (7) |
| N1 | 0.065 (4) | 0.046 (5) | 0.041 (4) | −0.010 (4) | −0.009 (3) | 0.001 (4) |
| O1 | 0.080 (4) | 0.090 (5) | 0.033 (4) | −0.009 (4) | −0.009 (3) | 0.007 (4) |
| O2 | 0.105 (6) | 0.115 (7) | 0.030 (4) | −0.014 (5) | 0.001 (3) | 0.012 (4) |
| O3 | 0.070 (4) | 0.068 (4) | 0.029 (3) | −0.017 (3) | −0.012 (3) | 0.007 (3) |
| O4 | 0.070 (4) | 0.060 (4) | 0.038 (4) | −0.012 (3) | −0.006 (3) | 0.002 (3) |
| O5 | 0.067 (4) | 0.090 (5) | 0.035 (4) | 0.015 (4) | 0.002 (3) | −0.002 (4) |
| O6 | 0.065 (4) | 0.102 (6) | 0.048 (4) | 0.026 (4) | −0.003 (3) | −0.011 (4) |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Geometric parameters (Å, º)
| C9—O2 | 1.223 (11) | C12—N1 | 1.451 (11) |
| C9—O1 | 1.369 (11) | C12—C13 | 1.490 (11) |
| C9—C8 | 1.433 (12) | C12—H12A | 0.9700 |
| C1—C2 | 1.350 (13) | C12—H12B | 0.9700 |
| C1—C6 | 1.394 (11) | C13—C14 | 1.391 (12) |
| C1—O1 | 1.399 (11) | C13—C18 | 1.400 (11) |
| C2—C3 | 1.381 (14) | C14—C15 | 1.367 (12) |
| C2—H2 | 0.9300 | C14—H14 | 0.9300 |
| C3—C4 | 1.389 (12) | C15—C16 | 1.386 (12) |
| C3—H3 | 0.9300 | C15—H15 | 0.9300 |
| C4—C5 | 1.343 (13) | C16—C17 | 1.372 (12) |
| C4—H4 | 0.9300 | C16—O6 | 1.379 (10) |
| C5—C6 | 1.417 (12) | C17—C18 | 1.382 (11) |
| C5—H5 | 0.9300 | C17—H17 | 0.9300 |
| C6—C7 | 1.398 (12) | C18—O5 | 1.369 (10) |
| C7—C8 | 1.352 (12) | C19—O5 | 1.428 (11) |
| C7—O3 | 1.373 (9) | C19—H19A | 0.9600 |
| C8—H8 | 0.9300 | C19—H19B | 0.9600 |
| C10—O3 | 1.399 (10) | C19—H19C | 0.9600 |
| C10—C11 | 1.516 (11) | C20—O6 | 1.421 (11) |
| C10—H10A | 0.9700 | C20—H20A | 0.9600 |
| C10—H10B | 0.9700 | C20—H20B | 0.9600 |
| C11—O4 | 1.239 (10) | C20—H20C | 0.9600 |
| C11—N1 | 1.315 (11) | N1—H1 | 0.8600 |
| O2—C9—O1 | 115.5 (8) | C13—C12—H12B | 108.3 |
| O2—C9—C8 | 125.3 (10) | H12A—C12—H12B | 107.4 |
| O1—C9—C8 | 119.0 (9) | C14—C13—C18 | 116.6 (7) |
| C2—C1—C6 | 123.5 (9) | C14—C13—C12 | 124.8 (8) |
| C2—C1—O1 | 117.0 (7) | C18—C13—C12 | 118.5 (7) |
| C6—C1—O1 | 119.4 (8) | C15—C14—C13 | 123.2 (9) |
| C1—C2—C3 | 118.7 (8) | C15—C14—H14 | 118.4 |
| C1—C2—H2 | 120.6 | C13—C14—H14 | 118.4 |
| C3—C2—H2 | 120.6 | C14—C15—C16 | 118.7 (8) |
| C2—C3—C4 | 119.9 (9) | C14—C15—H15 | 120.7 |
| C2—C3—H3 | 120.0 | C16—C15—H15 | 120.7 |
| C4—C3—H3 | 120.0 | C17—C16—O6 | 123.4 (7) |
| C5—C4—C3 | 120.8 (10) | C17—C16—C15 | 120.3 (8) |
| C5—C4—H4 | 119.6 | O6—C16—C15 | 116.4 (7) |
| C3—C4—H4 | 119.6 | C16—C17—C18 | 120.3 (8) |
| C4—C5—C6 | 121.1 (8) | C16—C17—H17 | 119.9 |
| C4—C5—H5 | 119.5 | C18—C17—H17 | 119.9 |
| C6—C5—H5 | 119.5 | O5—C18—C17 | 124.4 (8) |
| C1—C6—C7 | 118.6 (8) | O5—C18—C13 | 114.6 (7) |
| C1—C6—C5 | 116.0 (8) | C17—C18—C13 | 120.9 (8) |
| C7—C6—C5 | 125.4 (7) | O5—C19—H19A | 109.5 |
| C8—C7—O3 | 121.9 (8) | O5—C19—H19B | 109.5 |
| C8—C7—C6 | 122.6 (7) | H19A—C19—H19B | 109.5 |
| O3—C7—C6 | 115.4 (7) | O5—C19—H19C | 109.5 |
| C7—C8—C9 | 118.9 (9) | H19A—C19—H19C | 109.5 |
| C7—C8—H8 | 120.6 | H19B—C19—H19C | 109.5 |
| C9—C8—H8 | 120.6 | O6—C20—H20A | 109.5 |
| O3—C10—C11 | 110.6 (7) | O6—C20—H20B | 109.5 |
| O3—C10—H10A | 109.5 | H20A—C20—H20B | 109.5 |
| C11—C10—H10A | 109.5 | O6—C20—H20C | 109.5 |
| O3—C10—H10B | 109.5 | H20A—C20—H20C | 109.5 |
| C11—C10—H10B | 109.5 | H20B—C20—H20C | 109.5 |
| H10A—C10—H10B | 108.1 | C11—N1—C12 | 121.3 (7) |
| O4—C11—N1 | 123.7 (7) | C11—N1—H1 | 119.4 |
| O4—C11—C10 | 117.5 (8) | C12—N1—H1 | 119.4 |
| N1—C11—C10 | 118.8 (8) | C9—O1—C1 | 121.4 (7) |
| N1—C12—C13 | 115.9 (8) | C7—O3—C10 | 118.0 (6) |
| N1—C12—H12A | 108.3 | C18—O5—C19 | 117.5 (7) |
| C13—C12—H12A | 108.3 | C16—O6—C20 | 117.3 (7) |
| N1—C12—H12B | 108.3 | ||
| C6—C1—C2—C3 | 0.3 (16) | C13—C14—C15—C16 | −0.7 (17) |
| O1—C1—C2—C3 | 179.9 (9) | C14—C15—C16—C17 | −0.7 (16) |
| C1—C2—C3—C4 | −0.9 (17) | C14—C15—C16—O6 | 179.7 (10) |
| C2—C3—C4—C5 | 1.1 (17) | O6—C16—C17—C18 | −178.1 (9) |
| C3—C4—C5—C6 | −0.8 (17) | C15—C16—C17—C18 | 2.2 (15) |
| C2—C1—C6—C7 | −179.6 (10) | C16—C17—C18—O5 | 179.9 (9) |
| O1—C1—C6—C7 | 0.8 (13) | C16—C17—C18—C13 | −2.5 (15) |
| C2—C1—C6—C5 | 0.0 (14) | C14—C13—C18—O5 | 179.0 (8) |
| O1—C1—C6—C5 | −179.6 (9) | C12—C13—C18—O5 | −3.5 (12) |
| C4—C5—C6—C1 | 0.3 (15) | C14—C13—C18—C17 | 1.1 (13) |
| C4—C5—C6—C7 | 179.8 (10) | C12—C13—C18—C17 | 178.6 (9) |
| C1—C6—C7—C8 | −0.6 (14) | O4—C11—N1—C12 | −3.4 (13) |
| C5—C6—C7—C8 | 179.9 (10) | C10—C11—N1—C12 | 178.1 (8) |
| C1—C6—C7—O3 | −177.3 (8) | C13—C12—N1—C11 | 83.3 (11) |
| C5—C6—C7—O3 | 3.2 (14) | O2—C9—O1—C1 | 177.8 (9) |
| O3—C7—C8—C9 | 177.7 (9) | C8—C9—O1—C1 | 2.3 (15) |
| C6—C7—C8—C9 | 1.1 (14) | C2—C1—O1—C9 | 178.7 (10) |
| O2—C9—C8—C7 | −177.0 (11) | C6—C1—O1—C9 | −1.7 (13) |
| O1—C9—C8—C7 | −2.0 (15) | C8—C7—O3—C10 | −7.3 (12) |
| O3—C10—C11—O4 | 164.9 (8) | C6—C7—O3—C10 | 169.5 (8) |
| O3—C10—C11—N1 | −16.4 (11) | C11—C10—O3—C7 | −160.9 (7) |
| N1—C12—C13—C14 | 2.3 (14) | C17—C18—O5—C19 | −2.8 (13) |
| N1—C12—C13—C18 | −175.0 (8) | C13—C18—O5—C19 | 179.4 (10) |
| C18—C13—C14—C15 | 0.5 (15) | C17—C16—O6—C20 | 1.9 (14) |
| C12—C13—C14—C15 | −176.8 (10) | C15—C16—O6—C20 | −178.4 (11) |
N-(2,4-Dimethoxybenzyl)-2-[(2-oxo-2H-chromen-4-yl)oxy]acetamide (II) . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.86 | 2.31 | 2.669 (2) | 105 |
| C14—H14···N1 | 0.93 | 2.59 | 2.923 (2) | 101 |
| N1—H1···O4i | 0.86 | 2.09 | 2.900 (2) | 156 |
| C3—H3···O5ii | 0.93 | 2.49 | 3.419 (2) | 175 |
| C5—H5···O4i | 0.93 | 2.43 | 3.307 (2) | 157 |
| C15—H15···O4iii | 0.93 | 2.51 | 3.399 (2) | 160 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1; (iii) −x, y+1/2, −z+1.
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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) global, I, II. DOI: 10.1107/S2056989019003736/su5482sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019003736/su5482Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989019003736/su5482IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989019003736/su5482Isup4.cml
Supporting information file. DOI: 10.1107/S2056989019003736/su5482IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report