In the title compounds, (I) and (II), both of which crystallize in the monoclinic space group P21/n, the methyl acrylate and nitrovinyl units are relatively planar with an E conformation about the C=C bonds. The two aromatic rings are inclined to one another by 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In the crystal of (I), chains along the b axis are formed via C—H⋯O hydrogen bonds. In the crystal of (II), molecules are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane.
Keywords: crystal structure, 2-cyanoacrylates, phenyl acrylates, cinnamic acid derivatives, C—H⋯O hydrogen bonding
Abstract
The title compounds, C19H16ClNO5, (I), and C19H15Cl2NO5, (II), both crystallize in the monoclinic space group P21/n. They differ essentially in the orientation of the methyl acetate group, with the C=O bond directed towards the NO2 group in (I) but away from it in (II). In compound (I), the mean plane of the methyl acrylate unit is planar, with a maximum deviation of 0.0044 (2) Å for the methyl C atom, while in (II) this deviation is 0.0147 Å. The interplanar angles between the two aromatic rings are 74.87 (9) and 75.65 (2)° for compounds (I) and (II), respectively. In both compounds, the methyl acrylate and nitrovinyl groups each adopt an E conformation about the C=C bond. In the crystal of (I), molecules are linked by C—H⋯O hydrogen bonds forming chains along the b axis. The chains are linked via C—H⋯Cl hydrogen bonds, forming sheets parallel to the ab plane. The sheets are linked via C—H⋯π interactions, forming a three-dimensional structure. In the crystal of (II), molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(30) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane and enclosing R 4 4(28) ring motifs. The sheets are linked via parallel slipped π–π interactions (intercentroid distances are both ca 3.86 Å), forming a three-dimensional structure.
Chemical context
Recently, 2-cyanoacrylates have been used extensively as agrochemicals because of their unique mechanism of action and good environmental profiles (Govindan et al., 2011 ▸). Phenyl acrylates and their derivatives are important compounds because of their agrochemical and medical applications (De Fraine & Martin, 1991 ▸). Cinnamic acid derivatives have received attention in medicinal research as traditional as well as recently synthetic antitumor agents (De et al., 2011 ▸). They also possess significant antibacterial activity against Staphylococcus aureus (Xiao et al., 2008 ▸). In addition, different substitutions on the basic moiety lead to various pharmacological activities, such as anti-oxidant, hepatoprotective, anxiolytic, insect repellent, antidiabetic and anticholesterolemic (Sharma, 2011 ▸). Against this background, the title compounds were synthesized and we report herein on their crystal structures.
Structural commentary
The title compounds, (I) and (II), crystallized in the monoclinic space group P21/n with Z = 4; their molecular structures are illustrated in Figs. 1 ▸ and 2 ▸, respectively. In compound (I), the methyl acrylate unit is essentially planar, with a maximum deviation of 0.0044 (2) Å for atom C12, and forms dihedral angles of 84.04 (9) and 50.23 (9)° with the benzene rings (C3–C8) and (C14–C19), respectively. Likewise, in compound (II), the methyl acrylate unit is essentially planar, with a maximum deviation of 0.0147 (2) Å for atom C12, and forms dihedral angle of 73.20 (9) and 42.81 (9)° with benzene rings (C3–C8) and (C14–C19), respectively. In compound (I), the rings (C3–C8) and (C14–C19) are almost normal to one another, making a dihedral angle of 74.87 (9)°. In the case of compound (II), the corresponding dihedral angle is 75.65 (2)°. The title molecules exhibit structural similarities with the related structure, (Z)-methyl 3-(2,4-dichlorophenyl)-2-[(2-formylphenoxy)methyl]acrylate (Gangadharan et al., 2011 ▸).
Figure 1.
The molecular structure of compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
Figure 2.
The molecular structure of compound (II), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
The methyl acrylate moieties adopt an extended conformation, as is evident from the torsion angles O4—C11—C10—C13 = 170.6 (2)°, O5—C11—C10—C13 = −8.5 (2)°, C9—C10—C11—O4 = −5.5 (2)° and C9—C10—C11—O5 = 175.5 (1)° for compound (I), while the corresponding angles in compound (II) are −2.9 (5), 177.7 (3), 173.0 (3) and −6.3 (4)°, respectively. The extended conformation is supported by the fact that the bond angles involving the carbonyl O atoms are invariably enlarged (Schweizer & Dunitz, 1982 ▸).
The significant difference in the bond lengths O5—C11 and O5—C12, which are 1.324 (2) and 1.444 (2) Å, respectively, for compound (I), and 1.328 (4) and 1.440 (4) Å, respectively, for compound (II), can be attributed to a partial contribution from the O−—C=O+—C resonance structures of the O5—C11(=O4)—C10 group (Merlino et al., 1971 ▸). This feature, commonly observed for the carboxylic ester group of substituents in various compounds gives average values of 1.340 and 1.447 Å, respectively (Varghese et al., 1986 ▸).
In both compounds, the nitrovinyl groups [C2=C1—N1(O1,O2)], have an E conformation about the C2=C1 bond. In (I), its mean plane makes a dihedral angle of 2.025 (9)° with the benzene ring (C3–C8) to which it is attached, while in compound (II), the corresponding dihedral angle is much larger, at 14.78 (16) °.
Supramolecular features
In the crystal of (I), adjacent molecules are linked by C—H⋯O hydrogen bonds forming chains along the b-axis direction (Table 1 ▸ and Fig. 3 ▸). The chains are linked via C—H⋯Cl hydrogen bonds, forming sheets parallel to the ab plane (Fig. 4 ▸ and Table 1 ▸). The sheets are linked via C—H⋯π interactions, forming a three-dimensional structure (Table 1 ▸).
Table 1. Hydrogen-bond geometry (Å, °) for (I) .
Cg2 is the centroid of the C14–C19 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C12—H12A⋯O1i | 0.96 | 2.45 | 3.406 (2) | 172 |
| C2—H2⋯Cl1ii | 0.93 | 2.85 | 3.7515 (16) | 165 |
| C13—H13⋯Cg2iii | 0.93 | 2.91 | 3.5828 (16) | 130 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 3.
A partial view of the crystal structure of compound (I), showing the hydrogen-bonded (dashed lines) zigzag chains propagating along [010]; see Table 1 ▸.
Figure 4.
The crystal packing of compound (I), viewed along the c axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸).
In compound (II), molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers enclosing an 
(30) ring motif (Table 2 ▸ and Fig. 5 ▸). The dimers are linked by further C—H⋯O hydrogen bonds, forming sheets parallel to the ac plane and enclosing 
(28) ring motifs (Table 2 ▸ and Fig. 5 ▸). The sheets are linked via slipped parallel π–π interactions, forming a three-dimensional structure, Fig. 6 ▸ [Cg1⋯Cg1i = 3.863 (2) Å, inter-planar distance = 3.487 (1) Å, slippage 1.662 Å; Cg1 is the centroid of ring C3–C8; symmetry code: (i) −x + 1, −y, z + 1, and Cg2⋯Cg2ii = 3.861 (2) Å, inter-planar distance = 3.506 (2) Å, slippage = 1.617 Å; Cg2 is the centroid of ring C14–C19; symmetry code: (ii) −x + 1, −y, −z + 2].
Table 2. Hydrogen-bond geometry (Å, °) for (II) .
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C6—H6⋯O4i | 0.93 | 2.56 | 3.371 (4) | 146 |
| C7—H7⋯O2ii | 0.93 | 2.58 | 3.476 (4) | 161 |
| C18—H18⋯O1iii | 0.93 | 2.60 | 3.485 (5) | 160 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 5.
A partial view of the crystal packing of compound (II), viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 2 ▸).
Figure 6.
The crystal packing of compound (II), viewed along the c axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸).
Database survey
A search of the Cambridge Structural Database (CSD, Version 5.37, November 2015; Groom & Allen, 2014 ▸) for the substructure methyl (E)-2-(phenoxymethyl)-3-phenylacrylate gave 12 hits. There is a great variety in the dihedral angle involving the two aromatic rings; from a minimum of ca 47.2° in (E)-methyl 2-({2-ethoxy-6-[(E)-(hydroxyimino)methyl]phenoxy}methyl)-3-phenylacrylate (CSD code: ZARDAT; Govindan et al., 2012 ▸) to a maximum of ca 88.4° in methyl (E)-2-[(2-nitrophenoxy)methyl]-3-phenylacrylate (CSD code: PAWFIE; Anuradha et al., 2012 ▸). In the title compounds, this dihedral angle is 74.87 (9)° in (I) and 75.65 (2)° in (II).
Synthesis and crystallization
The title compounds were prepared in a similar manner using a mixture of methyl (E)-3-(2-chlorophenyl)-2-{[2-(2,2-dicyanovinyl)phenoxy]methyl}acrylate (1 mmol) for compound (I), and methyl (E)-2-{[4-chloro-2-(2,2-dicyanovinyl)phenoxy]methyl}-3-(2-chlorophenyl)acrylate (1 mol) for compound (II), dissolved in nitromethane (5 mol) in toluene (3 ml) with a catalytic amount of cinchona alkaloid (0.005 mmol %). The resulting solutions were stirred for 4 h at room temperature. The consumption of the starting materials was monitored by TLC. After completion of the reaction, DMAP (0.020 mol %) and di-tert-butyl dicarbonate (1.2 equiv) were added and the solutions of the corresponding crude products were stirred at 318–323 K for 2 h, followed by TLC (20% EtOAc and petroleum ether). The solvents were removed under reduced pressure and the residues purified by column chromatography on silica gel (3:97%, ethylacetate and petroleum ether) to afford pure products. The purified compounds were recrystallized from ethanol, by slow evaporation of the solvent, yielding block-like crystals of compounds (I) and (II), suitable for X ray diffraction analysis.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and allowed to ride on their parent atoms, with U iso(H) = 1.5U eq(C-methyl) and 1.2U eq(C) for other H atoms.
Table 3. Experimental details.
| (I) | (II) | |
|---|---|---|
| Crystal data | ||
| Chemical formula | C19H16ClNO5 | C19H15Cl2NO5 |
| M r | 373.78 | 408.22 |
| Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
| Temperature (K) | 293 | 293 |
| a, b, c (Å) | 9.0152 (3), 13.6579 (4), 14.6366 (4) | 9.2372 (3), 14.5027 (5), 14.4830 (5) |
| β (°) | 102.176 (1) | 94.521 (2) |
| V (Å3) | 1761.64 (9) | 1934.17 (11) |
| Z | 4 | 4 |
| Radiation type | Mo Kα | Mo Kα |
| μ (mm−1) | 0.25 | 0.37 |
| Crystal size (mm) | 0.27 × 0.24 × 0.18 | 0.28 × 0.22 × 0.19 |
| 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 | 0.935, 0.935 | 0.942, 0.961 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 15968, 4365, 3186 | 12108, 3481, 2382 |
| R int | 0.019 | 0.029 |
| (sin θ/λ)max (Å−1) | 0.667 | 0.600 |
| Refinement | ||
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.040, 0.109, 1.04 | 0.055, 0.143, 1.04 |
| No. of reflections | 4365 | 3481 |
| No. of parameters | 236 | 245 |
| H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.23, −0.23 | 0.57, −0.31 |
Supplementary Material
Crystal structure: contains datablock(s) global, I, II. DOI: 10.1107/S2056989016001493/su5265sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016001493/su5265Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989016001493/su5265IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989016001493/su5265Isup4.cml
Supporting information file. DOI: 10.1107/S2056989016001493/su5265IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Department of Chemistry, IIT, Chennai, India, for the X-ray intensity data collection.
supplementary crystallographic information
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Crystal data
| C19H16ClNO5 | F(000) = 776 |
| Mr = 373.78 | Dx = 1.409 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.0152 (3) Å | Cell parameters from 2595 reflections |
| b = 13.6579 (4) Å | θ = 2.1–25.0° |
| c = 14.6366 (4) Å | µ = 0.25 mm−1 |
| β = 102.176 (1)° | T = 293 K |
| V = 1761.64 (9) Å3 | Block, colourless |
| Z = 4 | 0.27 × 0.24 × 0.18 mm |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Data collection
| Bruker Kappa APEXII CCD diffractometer | 4365 independent reflections |
| Radiation source: fine-focus sealed tube | 3186 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.019 |
| ω and φ scans | θmax = 28.3°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −9→12 |
| Tmin = 0.935, Tmax = 0.935 | k = −9→18 |
| 15968 measured reflections | l = −19→19 |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.4238P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 4365 reflections | Δρmax = 0.23 e Å−3 |
| 236 parameters | Δρmin = −0.23 e Å−3 |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.94245 (6) | 0.33362 (3) | 1.09845 (3) | 0.06629 (16) | |
| O1 | 1.02396 (17) | 0.69069 (14) | 0.66665 (11) | 0.0909 (5) | |
| O2 | 0.88624 (18) | 0.72882 (13) | 0.53405 (12) | 0.0931 (5) | |
| O3 | 0.63790 (11) | 0.47698 (8) | 0.70425 (7) | 0.0448 (3) | |
| O4 | 0.81629 (15) | 0.27705 (11) | 0.67330 (8) | 0.0732 (4) | |
| O5 | 1.02681 (12) | 0.29776 (9) | 0.78215 (8) | 0.0572 (3) | |
| N1 | 0.90607 (17) | 0.68625 (11) | 0.60846 (11) | 0.0562 (4) | |
| C1 | 0.78561 (18) | 0.62664 (12) | 0.63151 (11) | 0.0480 (4) | |
| H1 | 0.8059 | 0.5842 | 0.6823 | 0.058* | |
| C2 | 0.64741 (18) | 0.63313 (11) | 0.57985 (10) | 0.0454 (4) | |
| H2 | 0.6373 | 0.6754 | 0.5291 | 0.054* | |
| C3 | 0.50814 (17) | 0.58452 (11) | 0.58984 (9) | 0.0420 (3) | |
| C4 | 0.3720 (2) | 0.61704 (14) | 0.53395 (11) | 0.0553 (4) | |
| H4 | 0.3738 | 0.6682 | 0.4923 | 0.066* | |
| C5 | 0.2351 (2) | 0.57515 (15) | 0.53901 (13) | 0.0645 (5) | |
| H5 | 0.1456 | 0.5985 | 0.5018 | 0.077* | |
| C6 | 0.2317 (2) | 0.49857 (15) | 0.59942 (13) | 0.0624 (5) | |
| H6 | 0.1392 | 0.4702 | 0.6029 | 0.075* | |
| C7 | 0.36441 (18) | 0.46297 (13) | 0.65535 (11) | 0.0512 (4) | |
| H7 | 0.3610 | 0.4105 | 0.6953 | 0.061* | |
| C8 | 0.50191 (17) | 0.50605 (11) | 0.65131 (9) | 0.0404 (3) | |
| C9 | 0.64005 (16) | 0.39327 (11) | 0.76435 (10) | 0.0415 (3) | |
| H9A | 0.5931 | 0.3375 | 0.7285 | 0.050* | |
| H9B | 0.5844 | 0.4074 | 0.8127 | 0.050* | |
| C10 | 0.80192 (16) | 0.37129 (10) | 0.80709 (9) | 0.0371 (3) | |
| C11 | 0.88048 (18) | 0.31119 (11) | 0.74673 (10) | 0.0421 (3) | |
| C12 | 1.1079 (2) | 0.23635 (15) | 0.72892 (14) | 0.0658 (5) | |
| H12A | 1.2107 | 0.2281 | 0.7627 | 0.099* | |
| H12B | 1.1078 | 0.2666 | 0.6697 | 0.099* | |
| H12C | 1.0593 | 0.1736 | 0.7190 | 0.099* | |
| C13 | 0.87143 (16) | 0.39681 (10) | 0.89424 (9) | 0.0387 (3) | |
| H13 | 0.9701 | 0.3744 | 0.9152 | 0.046* | |
| C14 | 0.80700 (16) | 0.45658 (11) | 0.95956 (10) | 0.0401 (3) | |
| C15 | 0.72385 (19) | 0.54180 (12) | 0.93057 (11) | 0.0503 (4) | |
| H15 | 0.7068 | 0.5599 | 0.8680 | 0.060* | |
| C16 | 0.6666 (2) | 0.59956 (14) | 0.99228 (13) | 0.0595 (4) | |
| H16 | 0.6118 | 0.6558 | 0.9713 | 0.071* | |
| C17 | 0.6908 (2) | 0.57362 (15) | 1.08512 (13) | 0.0616 (5) | |
| H17 | 0.6509 | 0.6120 | 1.1266 | 0.074* | |
| C18 | 0.7739 (2) | 0.49116 (14) | 1.11704 (11) | 0.0566 (4) | |
| H18 | 0.7907 | 0.4740 | 1.1799 | 0.068* | |
| C19 | 0.83196 (18) | 0.43422 (11) | 1.05485 (10) | 0.0448 (4) |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0968 (4) | 0.0562 (3) | 0.0402 (2) | 0.0052 (2) | 0.0017 (2) | 0.00662 (18) |
| O1 | 0.0637 (9) | 0.1316 (15) | 0.0765 (10) | −0.0259 (9) | 0.0127 (8) | −0.0043 (10) |
| O2 | 0.0839 (10) | 0.0980 (12) | 0.1021 (12) | −0.0038 (9) | 0.0300 (9) | 0.0478 (10) |
| O3 | 0.0423 (6) | 0.0458 (6) | 0.0437 (5) | 0.0003 (5) | 0.0033 (4) | 0.0125 (5) |
| O4 | 0.0721 (8) | 0.0937 (10) | 0.0474 (7) | 0.0174 (7) | −0.0020 (6) | −0.0269 (7) |
| O5 | 0.0500 (7) | 0.0665 (8) | 0.0533 (7) | 0.0096 (6) | 0.0071 (5) | −0.0167 (6) |
| N1 | 0.0609 (10) | 0.0516 (8) | 0.0611 (9) | 0.0006 (7) | 0.0237 (8) | −0.0041 (7) |
| C1 | 0.0572 (10) | 0.0432 (8) | 0.0456 (8) | 0.0012 (7) | 0.0154 (7) | 0.0017 (7) |
| C2 | 0.0615 (10) | 0.0366 (8) | 0.0392 (7) | 0.0090 (7) | 0.0131 (7) | 0.0024 (6) |
| C3 | 0.0519 (9) | 0.0397 (8) | 0.0332 (7) | 0.0087 (6) | 0.0060 (6) | −0.0041 (6) |
| C4 | 0.0617 (11) | 0.0563 (10) | 0.0435 (8) | 0.0161 (8) | 0.0007 (7) | 0.0005 (7) |
| C5 | 0.0525 (11) | 0.0774 (13) | 0.0558 (10) | 0.0168 (9) | −0.0065 (8) | −0.0059 (10) |
| C6 | 0.0430 (9) | 0.0790 (13) | 0.0621 (11) | −0.0005 (9) | 0.0038 (8) | −0.0137 (10) |
| C7 | 0.0489 (9) | 0.0589 (10) | 0.0447 (8) | −0.0015 (8) | 0.0077 (7) | −0.0020 (7) |
| C8 | 0.0437 (8) | 0.0436 (8) | 0.0325 (7) | 0.0051 (6) | 0.0045 (6) | −0.0055 (6) |
| C9 | 0.0457 (8) | 0.0394 (8) | 0.0387 (7) | −0.0033 (6) | 0.0074 (6) | 0.0042 (6) |
| C10 | 0.0456 (8) | 0.0313 (7) | 0.0345 (7) | −0.0012 (6) | 0.0089 (6) | 0.0048 (5) |
| C11 | 0.0532 (9) | 0.0383 (8) | 0.0341 (7) | 0.0024 (6) | 0.0079 (6) | 0.0036 (6) |
| C12 | 0.0612 (11) | 0.0704 (12) | 0.0683 (11) | 0.0132 (9) | 0.0196 (9) | −0.0120 (10) |
| C13 | 0.0440 (8) | 0.0355 (7) | 0.0362 (7) | 0.0002 (6) | 0.0075 (6) | 0.0045 (6) |
| C14 | 0.0433 (8) | 0.0398 (8) | 0.0373 (7) | −0.0053 (6) | 0.0089 (6) | −0.0030 (6) |
| C15 | 0.0577 (10) | 0.0482 (9) | 0.0452 (8) | 0.0031 (7) | 0.0110 (7) | −0.0020 (7) |
| C16 | 0.0591 (11) | 0.0536 (10) | 0.0671 (11) | 0.0078 (8) | 0.0165 (9) | −0.0100 (9) |
| C17 | 0.0613 (11) | 0.0664 (12) | 0.0635 (11) | −0.0070 (9) | 0.0277 (9) | −0.0227 (9) |
| C18 | 0.0688 (11) | 0.0644 (11) | 0.0405 (8) | −0.0168 (9) | 0.0203 (8) | −0.0109 (8) |
| C19 | 0.0515 (9) | 0.0438 (8) | 0.0386 (7) | −0.0101 (7) | 0.0082 (6) | −0.0037 (6) |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Geometric parameters (Å, º)
| Cl1—C19 | 1.7377 (17) | C7—H7 | 0.9300 |
| O1—N1 | 1.2152 (19) | C9—C10 | 1.492 (2) |
| O2—N1 | 1.214 (2) | C9—H9A | 0.9700 |
| O3—C8 | 1.3639 (17) | C9—H9B | 0.9700 |
| O3—C9 | 1.4403 (17) | C10—C13 | 1.3431 (19) |
| O4—C11 | 1.2022 (18) | C10—C11 | 1.490 (2) |
| O5—C11 | 1.3244 (19) | C12—H12A | 0.9600 |
| O5—C12 | 1.444 (2) | C12—H12B | 0.9600 |
| N1—C1 | 1.453 (2) | C12—H12C | 0.9600 |
| C1—C2 | 1.317 (2) | C13—C14 | 1.467 (2) |
| C1—H1 | 0.9300 | C13—H13 | 0.9300 |
| C2—C3 | 1.455 (2) | C14—C19 | 1.399 (2) |
| C2—H2 | 0.9300 | C14—C15 | 1.401 (2) |
| C3—C4 | 1.396 (2) | C15—C16 | 1.379 (2) |
| C3—C8 | 1.408 (2) | C15—H15 | 0.9300 |
| C4—C5 | 1.376 (3) | C16—C17 | 1.376 (3) |
| C4—H4 | 0.9300 | C16—H16 | 0.9300 |
| C5—C6 | 1.374 (3) | C17—C18 | 1.378 (3) |
| C5—H5 | 0.9300 | C17—H17 | 0.9300 |
| C6—C7 | 1.388 (2) | C18—C19 | 1.381 (2) |
| C6—H6 | 0.9300 | C18—H18 | 0.9300 |
| C7—C8 | 1.385 (2) | ||
| C8—O3—C9 | 118.21 (11) | H9A—C9—H9B | 108.5 |
| C11—O5—C12 | 116.44 (13) | C13—C10—C11 | 121.41 (13) |
| O2—N1—O1 | 123.12 (17) | C13—C10—C9 | 124.41 (13) |
| O2—N1—C1 | 120.05 (16) | C11—C10—C9 | 114.05 (12) |
| O1—N1—C1 | 116.83 (15) | O4—C11—O5 | 123.24 (14) |
| C2—C1—N1 | 119.47 (15) | O4—C11—C10 | 122.99 (15) |
| C2—C1—H1 | 120.3 | O5—C11—C10 | 113.77 (12) |
| N1—C1—H1 | 120.3 | O5—C12—H12A | 109.5 |
| C1—C2—C3 | 130.07 (15) | O5—C12—H12B | 109.5 |
| C1—C2—H2 | 115.0 | H12A—C12—H12B | 109.5 |
| C3—C2—H2 | 115.0 | O5—C12—H12C | 109.5 |
| C4—C3—C8 | 117.89 (15) | H12A—C12—H12C | 109.5 |
| C4—C3—C2 | 117.83 (15) | H12B—C12—H12C | 109.5 |
| C8—C3—C2 | 124.27 (13) | C10—C13—C14 | 126.43 (14) |
| C5—C4—C3 | 121.58 (17) | C10—C13—H13 | 116.8 |
| C5—C4—H4 | 119.2 | C14—C13—H13 | 116.8 |
| C3—C4—H4 | 119.2 | C19—C14—C15 | 116.54 (14) |
| C6—C5—C4 | 119.57 (16) | C19—C14—C13 | 121.72 (14) |
| C6—C5—H5 | 120.2 | C15—C14—C13 | 121.67 (13) |
| C4—C5—H5 | 120.2 | C16—C15—C14 | 121.82 (16) |
| C5—C6—C7 | 120.82 (18) | C16—C15—H15 | 119.1 |
| C5—C6—H6 | 119.6 | C14—C15—H15 | 119.1 |
| C7—C6—H6 | 119.6 | C17—C16—C15 | 119.73 (17) |
| C8—C7—C6 | 119.63 (17) | C17—C16—H16 | 120.1 |
| C8—C7—H7 | 120.2 | C15—C16—H16 | 120.1 |
| C6—C7—H7 | 120.2 | C16—C17—C18 | 120.45 (16) |
| O3—C8—C7 | 123.89 (14) | C16—C17—H17 | 119.8 |
| O3—C8—C3 | 115.62 (13) | C18—C17—H17 | 119.8 |
| C7—C8—C3 | 120.49 (14) | C17—C18—C19 | 119.40 (16) |
| O3—C9—C10 | 107.56 (11) | C17—C18—H18 | 120.3 |
| O3—C9—H9A | 110.2 | C19—C18—H18 | 120.3 |
| C10—C9—H9A | 110.2 | C18—C19—C14 | 122.04 (16) |
| O3—C9—H9B | 110.2 | C18—C19—Cl1 | 118.07 (13) |
| C10—C9—H9B | 110.2 | C14—C19—Cl1 | 119.87 (12) |
| O2—N1—C1—C2 | −12.4 (2) | C12—O5—C11—O4 | −1.8 (2) |
| O1—N1—C1—C2 | 167.54 (17) | C12—O5—C11—C10 | 177.29 (14) |
| N1—C1—C2—C3 | −177.77 (14) | C13—C10—C11—O4 | 170.56 (15) |
| C1—C2—C3—C4 | 169.58 (16) | C9—C10—C11—O4 | −5.5 (2) |
| C1—C2—C3—C8 | −11.3 (3) | C13—C10—C11—O5 | −8.5 (2) |
| C8—C3—C4—C5 | 0.8 (2) | C9—C10—C11—O5 | 175.47 (12) |
| C2—C3—C4—C5 | −179.97 (15) | C11—C10—C13—C14 | 179.10 (13) |
| C3—C4—C5—C6 | −0.9 (3) | C9—C10—C13—C14 | −5.3 (2) |
| C4—C5—C6—C7 | 0.0 (3) | C10—C13—C14—C19 | 139.80 (16) |
| C5—C6—C7—C8 | 1.0 (3) | C10—C13—C14—C15 | −43.5 (2) |
| C9—O3—C8—C7 | 3.4 (2) | C19—C14—C15—C16 | −1.4 (2) |
| C9—O3—C8—C3 | −176.32 (12) | C13—C14—C15—C16 | −178.25 (15) |
| C6—C7—C8—O3 | 179.22 (14) | C14—C15—C16—C17 | 0.0 (3) |
| C6—C7—C8—C3 | −1.0 (2) | C15—C16—C17—C18 | 1.0 (3) |
| C4—C3—C8—O3 | 179.92 (13) | C16—C17—C18—C19 | −0.4 (3) |
| C2—C3—C8—O3 | 0.8 (2) | C17—C18—C19—C14 | −1.1 (2) |
| C4—C3—C8—C7 | 0.2 (2) | C17—C18—C19—Cl1 | 177.47 (13) |
| C2—C3—C8—C7 | −178.99 (14) | C15—C14—C19—C18 | 2.0 (2) |
| C8—O3—C9—C10 | 174.75 (12) | C13—C14—C19—C18 | 178.82 (14) |
| O3—C9—C10—C13 | 100.78 (15) | C15—C14—C19—Cl1 | −176.57 (12) |
| O3—C9—C10—C11 | −83.34 (14) | C13—C14—C19—Cl1 | 0.3 (2) |
(I) Methyl (E)-3-(2-chlorophenyl)-2-({2-[(E)-2-nitrovinyl]phenoxy}methyl)acrylate . Hydrogen-bond geometry (Å, º)
Cg2 is the centroid of the C14–C19 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12A···O1i | 0.96 | 2.45 | 3.406 (2) | 172 |
| C2—H2···Cl1ii | 0.93 | 2.85 | 3.7515 (16) | 165 |
| C13—H13···Cg2iii | 0.93 | 2.91 | 3.5828 (16) | 130 |
Symmetry codes: (i) −x+5/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+2, −y+1, −z−3.
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Crystal data
| C19H15Cl2NO5 | F(000) = 840 |
| Mr = 408.22 | Dx = 1.402 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.2372 (3) Å | Cell parameters from 2355 reflections |
| b = 14.5027 (5) Å | θ = 2.0–25.0° |
| c = 14.4830 (5) Å | µ = 0.37 mm−1 |
| β = 94.521 (2)° | T = 293 K |
| V = 1934.17 (11) Å3 | Block, yellow |
| Z = 4 | 0.28 × 0.22 × 0.19 mm |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Data collection
| Bruker Kappa APEXII CCD diffractometer | 3481 independent reflections |
| Radiation source: fine-focus sealed tube | 2382 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| ω and φ scans | θmax = 25.2°, θmin = 2.0° |
| Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→10 |
| Tmin = 0.942, Tmax = 0.961 | k = −14→17 |
| 12108 measured reflections | l = −12→17 |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
| wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0555P)2 + 1.4111P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 3481 reflections | Δρmax = 0.56 e Å−3 |
| 245 parameters | Δρmin = −0.31 e Å−3 |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Special details
| Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.17238 (14) | 0.12004 (8) | 1.07720 (8) | 0.0933 (4) | |
| Cl2 | 0.41061 (13) | 0.09022 (7) | 0.31090 (6) | 0.0812 (4) | |
| O1 | 0.9540 (3) | 0.1694 (2) | 0.8133 (2) | 0.0860 (9) | |
| O2 | 0.9968 (3) | 0.1892 (2) | 0.6721 (2) | 0.0870 (9) | |
| O3 | 0.46144 (19) | 0.15787 (14) | 0.71181 (12) | 0.0405 (5) | |
| O4 | 0.4419 (3) | 0.35608 (16) | 0.93013 (16) | 0.0679 (7) | |
| O5 | 0.4219 (3) | 0.35463 (15) | 0.77613 (15) | 0.0611 (6) | |
| N1 | 0.9138 (3) | 0.17359 (19) | 0.7312 (2) | 0.0577 (7) | |
| C1 | 0.7610 (3) | 0.1607 (2) | 0.7049 (2) | 0.0490 (8) | |
| H1 | 0.6942 | 0.1598 | 0.7497 | 0.059* | |
| C2 | 0.7171 (3) | 0.1501 (2) | 0.6157 (2) | 0.0457 (7) | |
| H2 | 0.7904 | 0.1516 | 0.5753 | 0.055* | |
| C3 | 0.5725 (3) | 0.13660 (19) | 0.5727 (2) | 0.0403 (7) | |
| C4 | 0.5582 (4) | 0.1206 (2) | 0.4764 (2) | 0.0497 (8) | |
| H4 | 0.6407 | 0.1186 | 0.4437 | 0.060* | |
| C5 | 0.4247 (4) | 0.1082 (2) | 0.4307 (2) | 0.0500 (8) | |
| C6 | 0.3012 (4) | 0.1102 (2) | 0.4768 (2) | 0.0516 (8) | |
| H6 | 0.2111 | 0.1007 | 0.4449 | 0.062* | |
| C7 | 0.3112 (3) | 0.1264 (2) | 0.5709 (2) | 0.0439 (7) | |
| H7 | 0.2271 | 0.1282 | 0.6022 | 0.053* | |
| C8 | 0.4440 (3) | 0.13990 (18) | 0.61909 (18) | 0.0356 (7) | |
| C9 | 0.3311 (3) | 0.1789 (2) | 0.75710 (19) | 0.0405 (7) | |
| H9A | 0.2733 | 0.1236 | 0.7622 | 0.049* | |
| H9B | 0.2732 | 0.2241 | 0.7212 | 0.049* | |
| C10 | 0.3751 (3) | 0.2162 (2) | 0.85085 (19) | 0.0383 (7) | |
| C11 | 0.4169 (3) | 0.3154 (2) | 0.8587 (2) | 0.0446 (7) | |
| C12 | 0.4565 (5) | 0.4514 (2) | 0.7742 (3) | 0.0754 (11) | |
| H12A | 0.3927 | 0.4847 | 0.8114 | 0.113* | |
| H12B | 0.4448 | 0.4734 | 0.7116 | 0.113* | |
| H12C | 0.5553 | 0.4605 | 0.7985 | 0.113* | |
| C13 | 0.3713 (3) | 0.1683 (2) | 0.9294 (2) | 0.0427 (7) | |
| H13 | 0.3937 | 0.2004 | 0.9842 | 0.051* | |
| C14 | 0.3356 (3) | 0.0703 (2) | 0.93813 (19) | 0.0450 (7) | |
| C15 | 0.3945 (4) | 0.0031 (2) | 0.8832 (2) | 0.0538 (8) | |
| H15 | 0.4563 | 0.0207 | 0.8386 | 0.065* | |
| C16 | 0.3629 (4) | −0.0887 (2) | 0.8939 (3) | 0.0682 (11) | |
| H16 | 0.4031 | −0.1326 | 0.8567 | 0.082* | |
| C17 | 0.2720 (5) | −0.1158 (3) | 0.9593 (3) | 0.0780 (12) | |
| H17 | 0.2501 | −0.1779 | 0.9661 | 0.094* | |
| C18 | 0.2140 (5) | −0.0517 (3) | 1.0146 (3) | 0.0744 (11) | |
| H18 | 0.1525 | −0.0702 | 1.0589 | 0.089* | |
| C19 | 0.2458 (4) | 0.0402 (2) | 1.0050 (2) | 0.0570 (9) |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1329 (10) | 0.0784 (7) | 0.0764 (7) | −0.0237 (7) | 0.0577 (7) | −0.0153 (5) |
| Cl2 | 0.1300 (9) | 0.0795 (7) | 0.0346 (5) | −0.0058 (6) | 0.0091 (5) | −0.0058 (4) |
| O1 | 0.0641 (17) | 0.111 (2) | 0.080 (2) | −0.0158 (16) | −0.0138 (15) | 0.0255 (17) |
| O2 | 0.0459 (14) | 0.121 (2) | 0.097 (2) | −0.0142 (15) | 0.0225 (14) | −0.0075 (18) |
| O3 | 0.0360 (11) | 0.0520 (12) | 0.0340 (10) | 0.0031 (9) | 0.0067 (8) | −0.0017 (9) |
| O4 | 0.0971 (19) | 0.0564 (15) | 0.0523 (14) | −0.0270 (14) | 0.0186 (13) | −0.0149 (12) |
| O5 | 0.0910 (18) | 0.0397 (13) | 0.0527 (14) | −0.0054 (12) | 0.0057 (12) | 0.0067 (11) |
| N1 | 0.0494 (17) | 0.0518 (18) | 0.072 (2) | −0.0018 (14) | 0.0060 (16) | 0.0078 (15) |
| C1 | 0.0341 (17) | 0.052 (2) | 0.062 (2) | −0.0015 (14) | 0.0099 (14) | 0.0064 (16) |
| C2 | 0.0455 (18) | 0.0397 (17) | 0.0544 (19) | 0.0011 (14) | 0.0196 (15) | 0.0049 (15) |
| C3 | 0.0478 (18) | 0.0326 (16) | 0.0416 (16) | −0.0009 (13) | 0.0106 (13) | 0.0023 (13) |
| C4 | 0.066 (2) | 0.0406 (18) | 0.0448 (18) | −0.0007 (16) | 0.0217 (16) | 0.0034 (14) |
| C5 | 0.074 (2) | 0.0439 (18) | 0.0320 (16) | 0.0014 (17) | 0.0050 (16) | −0.0006 (14) |
| C6 | 0.060 (2) | 0.050 (2) | 0.0435 (18) | 0.0034 (16) | −0.0073 (15) | −0.0039 (15) |
| C7 | 0.0419 (17) | 0.0498 (19) | 0.0401 (16) | 0.0021 (14) | 0.0038 (13) | −0.0024 (14) |
| C8 | 0.0437 (17) | 0.0301 (15) | 0.0338 (15) | 0.0027 (13) | 0.0071 (12) | 0.0016 (12) |
| C9 | 0.0373 (16) | 0.0442 (17) | 0.0408 (16) | 0.0020 (13) | 0.0078 (12) | 0.0006 (13) |
| C10 | 0.0316 (15) | 0.0443 (18) | 0.0398 (16) | −0.0006 (13) | 0.0068 (12) | −0.0044 (13) |
| C11 | 0.0441 (18) | 0.0423 (18) | 0.0490 (19) | −0.0011 (14) | 0.0135 (14) | −0.0017 (15) |
| C12 | 0.097 (3) | 0.044 (2) | 0.086 (3) | −0.006 (2) | 0.010 (2) | 0.014 (2) |
| C13 | 0.0477 (18) | 0.0420 (18) | 0.0390 (16) | −0.0032 (14) | 0.0070 (13) | −0.0064 (14) |
| C14 | 0.0535 (19) | 0.0444 (18) | 0.0364 (16) | −0.0044 (15) | −0.0019 (14) | −0.0008 (14) |
| C15 | 0.066 (2) | 0.047 (2) | 0.0475 (18) | 0.0009 (17) | 0.0032 (16) | −0.0035 (16) |
| C16 | 0.091 (3) | 0.046 (2) | 0.066 (2) | 0.004 (2) | −0.005 (2) | −0.0083 (18) |
| C17 | 0.113 (4) | 0.039 (2) | 0.079 (3) | −0.018 (2) | −0.009 (3) | 0.007 (2) |
| C18 | 0.102 (3) | 0.061 (3) | 0.061 (2) | −0.030 (2) | 0.011 (2) | 0.007 (2) |
| C19 | 0.075 (2) | 0.054 (2) | 0.0432 (18) | −0.0142 (18) | 0.0092 (16) | −0.0003 (16) |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Geometric parameters (Å, º)
| Cl1—C19 | 1.734 (4) | C7—H7 | 0.9300 |
| Cl2—C5 | 1.749 (3) | C9—C10 | 1.488 (4) |
| O1—N1 | 1.220 (4) | C9—H9A | 0.9700 |
| O2—N1 | 1.215 (4) | C9—H9B | 0.9700 |
| O3—C8 | 1.365 (3) | C10—C13 | 1.336 (4) |
| O3—C9 | 1.448 (3) | C10—C11 | 1.491 (4) |
| O4—C11 | 1.198 (4) | C12—H12A | 0.9600 |
| O5—C11 | 1.328 (4) | C12—H12B | 0.9600 |
| O5—C12 | 1.440 (4) | C12—H12C | 0.9600 |
| N1—C1 | 1.444 (4) | C13—C14 | 1.467 (4) |
| C1—C2 | 1.332 (4) | C13—H13 | 0.9300 |
| C1—H1 | 0.9300 | C14—C19 | 1.393 (4) |
| C2—C3 | 1.442 (4) | C14—C15 | 1.396 (4) |
| C2—H2 | 0.9300 | C15—C16 | 1.374 (5) |
| C3—C4 | 1.409 (4) | C15—H15 | 0.9300 |
| C3—C8 | 1.410 (4) | C16—C17 | 1.372 (6) |
| C4—C5 | 1.365 (5) | C16—H16 | 0.9300 |
| C4—H4 | 0.9300 | C17—C18 | 1.364 (6) |
| C5—C6 | 1.367 (5) | C17—H17 | 0.9300 |
| C6—C7 | 1.379 (4) | C18—C19 | 1.374 (5) |
| C6—H6 | 0.9300 | C18—H18 | 0.9300 |
| C7—C8 | 1.378 (4) | ||
| C8—O3—C9 | 116.6 (2) | H9A—C9—H9B | 108.4 |
| C11—O5—C12 | 117.3 (3) | C13—C10—C9 | 124.4 (3) |
| O2—N1—O1 | 122.4 (3) | C13—C10—C11 | 117.5 (3) |
| O2—N1—C1 | 119.8 (3) | C9—C10—C11 | 118.0 (2) |
| O1—N1—C1 | 117.8 (3) | O4—C11—O5 | 123.3 (3) |
| C2—C1—N1 | 119.1 (3) | O4—C11—C10 | 124.9 (3) |
| C2—C1—H1 | 120.4 | O5—C11—C10 | 111.8 (3) |
| N1—C1—H1 | 120.4 | O5—C12—H12A | 109.5 |
| C1—C2—C3 | 129.5 (3) | O5—C12—H12B | 109.5 |
| C1—C2—H2 | 115.3 | H12A—C12—H12B | 109.5 |
| C3—C2—H2 | 115.3 | O5—C12—H12C | 109.5 |
| C4—C3—C8 | 117.4 (3) | H12A—C12—H12C | 109.5 |
| C4—C3—C2 | 117.5 (3) | H12B—C12—H12C | 109.5 |
| C8—C3—C2 | 125.1 (3) | C10—C13—C14 | 126.8 (3) |
| C5—C4—C3 | 120.8 (3) | C10—C13—H13 | 116.6 |
| C5—C4—H4 | 119.6 | C14—C13—H13 | 116.6 |
| C3—C4—H4 | 119.6 | C19—C14—C15 | 117.3 (3) |
| C4—C5—C6 | 121.1 (3) | C19—C14—C13 | 120.9 (3) |
| C4—C5—Cl2 | 119.7 (3) | C15—C14—C13 | 121.8 (3) |
| C6—C5—Cl2 | 119.2 (3) | C16—C15—C14 | 121.1 (3) |
| C5—C6—C7 | 119.5 (3) | C16—C15—H15 | 119.5 |
| C5—C6—H6 | 120.2 | C14—C15—H15 | 119.5 |
| C7—C6—H6 | 120.2 | C17—C16—C15 | 120.2 (4) |
| C8—C7—C6 | 120.9 (3) | C17—C16—H16 | 119.9 |
| C8—C7—H7 | 119.6 | C15—C16—H16 | 119.9 |
| C6—C7—H7 | 119.6 | C18—C17—C16 | 120.0 (3) |
| O3—C8—C7 | 123.9 (2) | C18—C17—H17 | 120.0 |
| O3—C8—C3 | 115.9 (2) | C16—C17—H17 | 120.0 |
| C7—C8—C3 | 120.2 (3) | C17—C18—C19 | 120.3 (4) |
| O3—C9—C10 | 108.2 (2) | C17—C18—H18 | 119.8 |
| O3—C9—H9A | 110.1 | C19—C18—H18 | 119.8 |
| C10—C9—H9A | 110.1 | C18—C19—C14 | 121.1 (3) |
| O3—C9—H9B | 110.1 | C18—C19—Cl1 | 119.3 (3) |
| C10—C9—H9B | 110.1 | C14—C19—Cl1 | 119.5 (3) |
| O2—N1—C1—C2 | 11.6 (5) | O3—C9—C10—C11 | 81.2 (3) |
| O1—N1—C1—C2 | −169.3 (3) | C12—O5—C11—O4 | −1.3 (5) |
| N1—C1—C2—C3 | −179.8 (3) | C12—O5—C11—C10 | 178.1 (3) |
| C1—C2—C3—C4 | −175.6 (3) | C13—C10—C11—O4 | −2.9 (5) |
| C1—C2—C3—C8 | 5.8 (5) | C9—C10—C11—O4 | 173.0 (3) |
| C8—C3—C4—C5 | −0.5 (4) | C13—C10—C11—O5 | 177.7 (3) |
| C2—C3—C4—C5 | −179.3 (3) | C9—C10—C11—O5 | −6.3 (4) |
| C3—C4—C5—C6 | −0.4 (5) | C9—C10—C13—C14 | 5.3 (5) |
| C3—C4—C5—Cl2 | 179.1 (2) | C11—C10—C13—C14 | −179.0 (3) |
| C4—C5—C6—C7 | 1.0 (5) | C10—C13—C14—C19 | −137.2 (3) |
| Cl2—C5—C6—C7 | −178.5 (2) | C10—C13—C14—C15 | 45.7 (4) |
| C5—C6—C7—C8 | −0.5 (5) | C19—C14—C15—C16 | 1.1 (5) |
| C9—O3—C8—C7 | −10.8 (4) | C13—C14—C15—C16 | 178.3 (3) |
| C9—O3—C8—C3 | 168.6 (2) | C14—C15—C16—C17 | 0.0 (5) |
| C6—C7—C8—O3 | 178.8 (3) | C15—C16—C17—C18 | −0.6 (6) |
| C6—C7—C8—C3 | −0.5 (4) | C16—C17—C18—C19 | 0.0 (6) |
| C4—C3—C8—O3 | −178.3 (2) | C17—C18—C19—C14 | 1.1 (6) |
| C2—C3—C8—O3 | 0.3 (4) | C17—C18—C19—Cl1 | −179.1 (3) |
| C4—C3—C8—C7 | 1.0 (4) | C15—C14—C19—C18 | −1.7 (5) |
| C2—C3—C8—C7 | 179.7 (3) | C13—C14—C19—C18 | −178.9 (3) |
| C8—O3—C9—C10 | −167.7 (2) | C15—C14—C19—Cl1 | 178.6 (2) |
| O3—C9—C10—C13 | −103.1 (3) | C13—C14—C19—Cl1 | 1.4 (4) |
(II) Methyl (E)-2-({4-chloro-2-[(E)-2-nitrovinyl]phenoxy}methyl)-3-(2-chlorophenyl)acrylate . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C6—H6···O4i | 0.93 | 2.56 | 3.371 (4) | 146 |
| C7—H7···O2ii | 0.93 | 2.58 | 3.476 (4) | 161 |
| C18—H18···O1iii | 0.93 | 2.60 | 3.485 (5) | 160 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, −y, −z+2.
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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/S2056989016001493/su5265sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016001493/su5265Isup2.hkl
Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989016001493/su5265IIsup3.hkl
Supporting information file. DOI: 10.1107/S2056989016001493/su5265Isup4.cml
Supporting information file. DOI: 10.1107/S2056989016001493/su5265IIsup5.cml
Additional supporting information: crystallographic information; 3D view; checkCIF report