organic compounds
Diethyl 1-[(4-methyl-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)methyl]-1H-1,2,3-triazole-4,5-dicarboxylate
aFormation Doctorale Molécules Bioactives, Santé et Biotechnologies, Centre détudes Doctorales Sciences et Technologies, Faculté des Sciences Dhar El Marhaz, Fès, Morocco, bLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and cLaboratoire de Chimie des Matériaux et Biotechnologie des Produits Naturels, E.Ma.Me.P.S., Université Moulay Ismail, Faculté des Sciences, Meknès, Morocco
*Correspondence e-mail: anouar.alami@usmba.ac.ma
In the title compound, C19H22N4O5, the central triazole ring makes dihedral angles of 56.15 (8) and 43.25 (9)° with the oxazole and benzene rings, respectively. The mean planes of the two ethoxycarbonyl groups make dihedral angles of 24.16 (11) and 51.90 (10)° with the triazole ring. Globally, the molecule has a U-shape. In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into supramolecular layers in the bc plane.
Keywords: crystal structure; 1,2,3-triazole moiety; hydrogen bonds.
CCDC reference: 1587658
Structure description
Azide–alkyne cycloaddition is a useful and convenient method for the preparation of 1,2,3-triazoles (Lutz et al., 2008; Oliva et al., 2008; Kiss et al., 2010). The approach for the synthesis of 1,2,3-triazole-substituted compounds involves transformation of the azide function in a 1,3-dipolar cycloaddition reaction with acetylene derivatives. In this context, the title compound was obtained with good yield (Boukhssas et al., 2017).
In the title compound, Fig. 1, the central triazole ring is planar (r.m.s deviation = 0.0054 (13) Å) and makes dihedral angles of 56.15 (8) and 43.25 (9)° with the oxazol and benzene rings, respectively. The mean planes of the two ethoxycarbonyl groups make dihedral angles of 24.16 (11) and 51.90 (10)° with the triazole ring.
In the crystal, molecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into supramolecular layers in the bc plane, Table 1 and Fig. 2.
Synthesis and crystallization
A mixture of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole (0.65 mmol) and diethyl acetylenedicarboxylate (0.65 mmol) was stirred for 12 h. The crude product was treated with ethyl acetate, the organic layer was washed with water, dried with Na2SO4, and the solvent removed. The product was purified by recrystallization from ether–hexane to afford the pure product. Suitable crystals of the title compound were obtained by recrystallization from its CHCl3 solution. The structure of the product was established on the basis of NMR spectroscopy (1H and 13C) and MS data.
Yield = 75% (white solid); m.p. = 92–94°C; Rf = 0.23 (ether/hexane). 1H NMR (300.13 MHz; CDCl3): 1.30 (3H, CH3–CH2, t, J = 7.15 Hz); 1.38 (3H, CH3–CH2, t, J = 7.14 Hz); 1.41 (3H, CH3–Oxaz, s); 4.13–4.53 (2H, CH2–Oxaz, AB, J = 9.05 Hz); 4.24–4.38 (2H, –CH2–CH3, q, J = 7.15 Hz); 4.27–4.42 (2H, –CH2–CH3, q, J = 7.15 Hz); 4.76–4.93 (2H, --CH2–triazole, AB, J = 13.76 Hz); 7.35–7.84 (5Harom, m). 13C NMR (75.47 MHz; CDCl3): 13.66 (CH3–CH2); 14.14 (CH3–CH2); 25.22 (CH3–Oxaz); 56.38 (CH2–triazole); 61.71 (CH3–CH2); 62.76 (CH3–CH2); 70.77 (Cq–Oxaz); 75.13 (CH2–Oxaz); 127.00 (C-5, of triazole ring); 128.21; 128.46; 131.74 and 132.06 (6 Carom); 139.60 (C-4, of triazole ring); 158.73 and 159.93 (CO); 164.46 (CN). MS–EI: [M+1]+= 387.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1587658
https://doi.org/10.1107/S2414314617017011/tk4040sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017011/tk4040Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617017011/tk4040Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C19H22N4O5 | F(000) = 816 |
Mr = 386.41 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 298 reflections |
a = 13.9450 (9) Å | θ = 1.4–28.4° |
b = 16.3245 (10) Å | µ = 0.10 mm−1 |
c = 9.0473 (6) Å | T = 173 K |
β = 104.066 (2)° | Prism, colourless |
V = 1997.8 (2) Å3 | 0.34 × 0.21 × 0.17 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2938 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
φ and ω scan | h = −16→16 |
33174 measured reflections | k = −19→19 |
3529 independent reflections | l = −10→10 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.3505P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.24 e Å−3 |
3529 reflections | Δρmin = −0.26 e Å−3 |
257 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0066 (12) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.91074 (9) | 0.92709 (7) | −0.10242 (14) | 0.0694 (4) | |
O2 | 0.75141 (8) | 0.95729 (7) | −0.11812 (12) | 0.0566 (3) | |
O3 | 0.78857 (14) | 1.13220 (8) | −0.14989 (14) | 0.0965 (5) | |
O4 | 0.76719 (8) | 1.21752 (6) | 0.03184 (11) | 0.0509 (3) | |
O5 | 0.75886 (7) | 0.88651 (7) | 0.37008 (12) | 0.0594 (3) | |
N1 | 0.92249 (8) | 0.98814 (7) | 0.22234 (13) | 0.0422 (3) | |
N2 | 0.93045 (9) | 1.05074 (7) | 0.32281 (14) | 0.0503 (3) | |
N3 | 0.88258 (9) | 1.11341 (7) | 0.25090 (13) | 0.0485 (3) | |
N4 | 0.82672 (9) | 0.82643 (7) | 0.19534 (14) | 0.0495 (3) | |
C1 | 0.86797 (9) | 1.01117 (8) | 0.08517 (15) | 0.0401 (3) | |
C2 | 0.84362 (10) | 1.09149 (8) | 0.10399 (15) | 0.0421 (3) | |
C3 | 0.84737 (11) | 0.95944 (9) | −0.05463 (16) | 0.0465 (3) | |
C4 | 0.72235 (16) | 0.91941 (14) | −0.2678 (2) | 0.0810 (6) | |
H4A | 0.7292 | 0.8604 | −0.2587 | 0.097* | |
H4B | 0.7642 | 0.9389 | −0.3317 | 0.097* | |
C5 | 0.61798 (18) | 0.94152 (15) | −0.3363 (2) | 0.0955 (7) | |
H5A | 0.5771 | 0.9219 | −0.2723 | 0.143* | |
H5B | 0.5971 | 0.9170 | −0.4353 | 0.143* | |
H5C | 0.6121 | 1.0000 | −0.3455 | 0.143* | |
C6 | 0.79680 (12) | 1.14840 (9) | −0.01821 (16) | 0.0506 (4) | |
C7 | 0.72300 (14) | 1.27614 (10) | −0.08724 (19) | 0.0635 (4) | |
H7A | 0.6618 | 1.2543 | −0.1497 | 0.076* | |
H7B | 0.7678 | 1.2865 | −0.1522 | 0.076* | |
C8 | 0.7035 (2) | 1.35238 (13) | −0.0141 (2) | 0.1027 (8) | |
H8A | 0.6570 | 1.3421 | 0.0463 | 0.154* | |
H8B | 0.6768 | 1.3924 | −0.0909 | 0.154* | |
H8C | 0.7641 | 1.3726 | 0.0500 | 0.154* | |
C9 | 0.97441 (10) | 0.91127 (9) | 0.27105 (18) | 0.0484 (4) | |
H9A | 1.0317 | 0.9228 | 0.3536 | 0.058* | |
H9B | 0.9981 | 0.8892 | 0.1869 | 0.058* | |
C10 | 0.91134 (10) | 0.84644 (8) | 0.32417 (17) | 0.0480 (4) | |
C11 | 0.97659 (14) | 0.77174 (10) | 0.3755 (2) | 0.0743 (5) | |
H11A | 0.9375 | 0.7284 | 0.4023 | 0.111* | |
H11B | 1.0286 | 0.7859 | 0.4625 | 0.111* | |
H11C | 1.0047 | 0.7539 | 0.2941 | 0.111* | |
C12 | 0.86204 (11) | 0.87770 (11) | 0.44759 (17) | 0.0558 (4) | |
H12A | 0.8702 | 0.8387 | 0.5306 | 0.067* | |
H12B | 0.8900 | 0.9299 | 0.4880 | 0.067* | |
C13 | 0.74973 (10) | 0.85130 (8) | 0.23094 (16) | 0.0448 (3) | |
C14 | 0.64819 (10) | 0.84697 (9) | 0.13450 (17) | 0.0477 (4) | |
C15 | 0.57447 (12) | 0.89708 (11) | 0.1616 (2) | 0.0630 (4) | |
H15 | 0.5883 | 0.9334 | 0.2433 | 0.076* | |
C16 | 0.48023 (13) | 0.89344 (14) | 0.0675 (2) | 0.0753 (5) | |
H16 | 0.4309 | 0.9275 | 0.0857 | 0.090* | |
C17 | 0.45948 (13) | 0.83999 (14) | −0.0518 (2) | 0.0778 (6) | |
H17 | 0.3961 | 0.8378 | −0.1152 | 0.093* | |
C18 | 0.53193 (14) | 0.78945 (14) | −0.0784 (2) | 0.0795 (6) | |
H18 | 0.5172 | 0.7526 | −0.1591 | 0.095* | |
C19 | 0.62626 (13) | 0.79287 (11) | 0.0134 (2) | 0.0630 (4) | |
H19 | 0.6753 | 0.7588 | −0.0061 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0646 (7) | 0.0756 (8) | 0.0763 (8) | −0.0012 (6) | 0.0331 (6) | −0.0257 (6) |
O2 | 0.0532 (6) | 0.0723 (7) | 0.0424 (6) | −0.0056 (5) | 0.0080 (5) | −0.0191 (5) |
O3 | 0.1746 (16) | 0.0726 (8) | 0.0387 (7) | 0.0207 (9) | 0.0192 (8) | 0.0032 (6) |
O4 | 0.0572 (6) | 0.0520 (6) | 0.0406 (6) | 0.0088 (5) | 0.0060 (5) | 0.0069 (4) |
O5 | 0.0456 (6) | 0.0838 (8) | 0.0460 (6) | −0.0019 (5) | 0.0058 (5) | −0.0103 (5) |
N1 | 0.0384 (6) | 0.0426 (6) | 0.0439 (6) | −0.0020 (5) | 0.0067 (5) | −0.0030 (5) |
N2 | 0.0558 (7) | 0.0458 (7) | 0.0431 (7) | −0.0008 (6) | −0.0001 (6) | −0.0041 (5) |
N3 | 0.0561 (7) | 0.0454 (6) | 0.0396 (7) | 0.0007 (5) | 0.0031 (5) | −0.0038 (5) |
N4 | 0.0424 (7) | 0.0503 (7) | 0.0520 (7) | −0.0029 (5) | 0.0040 (6) | −0.0057 (5) |
C1 | 0.0364 (7) | 0.0449 (7) | 0.0399 (7) | −0.0048 (6) | 0.0110 (6) | −0.0033 (6) |
C2 | 0.0433 (7) | 0.0457 (7) | 0.0370 (7) | −0.0035 (6) | 0.0093 (6) | −0.0027 (6) |
C3 | 0.0515 (9) | 0.0460 (7) | 0.0458 (8) | −0.0048 (6) | 0.0189 (7) | −0.0065 (6) |
C4 | 0.0879 (14) | 0.0981 (14) | 0.0515 (10) | −0.0074 (11) | 0.0062 (10) | −0.0337 (10) |
C5 | 0.0958 (16) | 0.1154 (18) | 0.0590 (12) | −0.0133 (13) | −0.0128 (11) | −0.0138 (11) |
C6 | 0.0610 (9) | 0.0516 (8) | 0.0389 (8) | −0.0037 (7) | 0.0114 (7) | 0.0004 (6) |
C7 | 0.0762 (11) | 0.0596 (10) | 0.0493 (9) | 0.0064 (8) | 0.0048 (8) | 0.0160 (7) |
C8 | 0.159 (2) | 0.0744 (13) | 0.0639 (12) | 0.0469 (14) | 0.0051 (14) | 0.0081 (10) |
C9 | 0.0365 (7) | 0.0488 (8) | 0.0574 (9) | 0.0061 (6) | 0.0064 (6) | −0.0003 (7) |
C10 | 0.0415 (8) | 0.0449 (7) | 0.0518 (9) | −0.0004 (6) | 0.0002 (6) | −0.0002 (6) |
C11 | 0.0688 (11) | 0.0511 (9) | 0.0917 (14) | 0.0070 (8) | −0.0024 (10) | 0.0086 (9) |
C12 | 0.0470 (8) | 0.0709 (10) | 0.0446 (8) | −0.0075 (7) | 0.0018 (7) | 0.0023 (7) |
C13 | 0.0461 (8) | 0.0425 (7) | 0.0440 (8) | −0.0071 (6) | 0.0077 (6) | 0.0008 (6) |
C14 | 0.0416 (8) | 0.0529 (8) | 0.0474 (8) | −0.0087 (6) | 0.0084 (6) | 0.0021 (7) |
C15 | 0.0499 (9) | 0.0755 (11) | 0.0604 (10) | −0.0015 (8) | 0.0073 (8) | −0.0110 (8) |
C16 | 0.0457 (9) | 0.1039 (14) | 0.0738 (12) | 0.0070 (9) | 0.0100 (9) | −0.0087 (11) |
C17 | 0.0439 (9) | 0.1183 (16) | 0.0649 (12) | −0.0127 (10) | 0.0011 (8) | −0.0090 (11) |
C18 | 0.0589 (11) | 0.1041 (15) | 0.0685 (12) | −0.0138 (10) | 0.0020 (9) | −0.0284 (11) |
C19 | 0.0492 (9) | 0.0733 (11) | 0.0633 (10) | −0.0064 (8) | 0.0075 (8) | −0.0149 (8) |
O1—C3 | 1.1969 (17) | C7—H7B | 0.9700 |
O2—C3 | 1.3222 (18) | C8—H8A | 0.9600 |
O2—C4 | 1.4543 (19) | C8—H8B | 0.9600 |
O3—C6 | 1.1983 (18) | C8—H8C | 0.9600 |
O4—C6 | 1.3190 (18) | C9—C10 | 1.526 (2) |
O4—C7 | 1.4606 (18) | C9—H9A | 0.9700 |
O5—C13 | 1.3614 (17) | C9—H9B | 0.9700 |
O5—C12 | 1.4464 (18) | C10—C11 | 1.525 (2) |
N1—C1 | 1.3419 (17) | C10—C12 | 1.534 (2) |
N1—N2 | 1.3542 (16) | C11—H11A | 0.9600 |
N1—C9 | 1.4622 (18) | C11—H11B | 0.9600 |
N2—N3 | 1.3055 (16) | C11—H11C | 0.9600 |
N3—C2 | 1.3561 (17) | C12—H12A | 0.9700 |
N4—C13 | 1.2607 (18) | C12—H12B | 0.9700 |
N4—C10 | 1.4795 (19) | C13—C14 | 1.473 (2) |
C1—C2 | 1.3753 (19) | C14—C15 | 1.382 (2) |
C1—C3 | 1.4896 (19) | C14—C19 | 1.383 (2) |
C2—C6 | 1.470 (2) | C15—C16 | 1.383 (2) |
C4—C5 | 1.481 (3) | C15—H15 | 0.9300 |
C4—H4A | 0.9700 | C16—C17 | 1.364 (3) |
C4—H4B | 0.9700 | C16—H16 | 0.9300 |
C5—H5A | 0.9600 | C17—C18 | 1.370 (3) |
C5—H5B | 0.9600 | C17—H17 | 0.9300 |
C5—H5C | 0.9600 | C18—C19 | 1.376 (3) |
C7—C8 | 1.465 (3) | C18—H18 | 0.9300 |
C7—H7A | 0.9700 | C19—H19 | 0.9300 |
C3—O2—C4 | 116.06 (12) | N1—C9—C10 | 114.14 (11) |
C6—O4—C7 | 114.73 (12) | N1—C9—H9A | 108.7 |
C13—O5—C12 | 105.35 (11) | C10—C9—H9A | 108.7 |
C1—N1—N2 | 110.18 (11) | N1—C9—H9B | 108.7 |
C1—N1—C9 | 130.31 (12) | C10—C9—H9B | 108.7 |
N2—N1—C9 | 119.44 (11) | H9A—C9—H9B | 107.6 |
N3—N2—N1 | 107.95 (11) | N4—C10—C11 | 111.47 (12) |
N2—N3—C2 | 108.44 (11) | N4—C10—C9 | 108.38 (12) |
C13—N4—C10 | 107.05 (12) | C11—C10—C9 | 107.67 (13) |
N1—C1—C2 | 104.72 (11) | N4—C10—C12 | 103.54 (11) |
N1—C1—C3 | 125.13 (12) | C11—C10—C12 | 112.58 (14) |
C2—C1—C3 | 130.02 (13) | C9—C10—C12 | 113.14 (12) |
N3—C2—C1 | 108.70 (12) | C10—C11—H11A | 109.5 |
N3—C2—C6 | 124.71 (12) | C10—C11—H11B | 109.5 |
C1—C2—C6 | 125.97 (12) | H11A—C11—H11B | 109.5 |
O1—C3—O2 | 126.13 (14) | C10—C11—H11C | 109.5 |
O1—C3—C1 | 123.36 (14) | H11A—C11—H11C | 109.5 |
O2—C3—C1 | 110.48 (11) | H11B—C11—H11C | 109.5 |
O2—C4—C5 | 107.98 (16) | O5—C12—C10 | 104.43 (11) |
O2—C4—H4A | 110.1 | O5—C12—H12A | 110.9 |
C5—C4—H4A | 110.1 | C10—C12—H12A | 110.9 |
O2—C4—H4B | 110.1 | O5—C12—H12B | 110.9 |
C5—C4—H4B | 110.1 | C10—C12—H12B | 110.9 |
H4A—C4—H4B | 108.4 | H12A—C12—H12B | 108.9 |
C4—C5—H5A | 109.5 | N4—C13—O5 | 118.56 (13) |
C4—C5—H5B | 109.5 | N4—C13—C14 | 126.07 (13) |
H5A—C5—H5B | 109.5 | O5—C13—C14 | 115.36 (12) |
C4—C5—H5C | 109.5 | C15—C14—C19 | 119.22 (15) |
H5A—C5—H5C | 109.5 | C15—C14—C13 | 121.06 (14) |
H5B—C5—H5C | 109.5 | C19—C14—C13 | 119.71 (14) |
O3—C6—O4 | 124.59 (14) | C14—C15—C16 | 120.15 (16) |
O3—C6—C2 | 121.74 (14) | C14—C15—H15 | 119.9 |
O4—C6—C2 | 113.66 (12) | C16—C15—H15 | 119.9 |
O4—C7—C8 | 108.35 (14) | C17—C16—C15 | 120.13 (18) |
O4—C7—H7A | 110.0 | C17—C16—H16 | 119.9 |
C8—C7—H7A | 110.0 | C15—C16—H16 | 119.9 |
O4—C7—H7B | 110.0 | C16—C17—C18 | 120.06 (17) |
C8—C7—H7B | 110.0 | C16—C17—H17 | 120.0 |
H7A—C7—H7B | 108.4 | C18—C17—H17 | 120.0 |
C7—C8—H8A | 109.5 | C17—C18—C19 | 120.48 (18) |
C7—C8—H8B | 109.5 | C17—C18—H18 | 119.8 |
H8A—C8—H8B | 109.5 | C19—C18—H18 | 119.8 |
C7—C8—H8C | 109.5 | C18—C19—C14 | 119.95 (17) |
H8A—C8—H8C | 109.5 | C18—C19—H19 | 120.0 |
H8B—C8—H8C | 109.5 | C14—C19—H19 | 120.0 |
C1—N1—N2—N3 | −0.62 (15) | N2—N1—C9—C10 | 95.08 (15) |
C9—N1—N2—N3 | 176.55 (11) | C13—N4—C10—C11 | 128.55 (15) |
N1—N2—N3—C2 | −0.01 (15) | C13—N4—C10—C9 | −113.13 (13) |
N2—N1—C1—C2 | 0.96 (14) | C13—N4—C10—C12 | 7.27 (15) |
C9—N1—C1—C2 | −175.80 (12) | N1—C9—C10—N4 | 61.10 (16) |
N2—N1—C1—C3 | 177.17 (12) | N1—C9—C10—C11 | −178.19 (13) |
C9—N1—C1—C3 | 0.4 (2) | N1—C9—C10—C12 | −53.13 (16) |
N2—N3—C2—C1 | 0.61 (16) | C13—O5—C12—C10 | 9.24 (15) |
N2—N3—C2—C6 | −170.79 (13) | N4—C10—C12—O5 | −10.01 (15) |
N1—C1—C2—N3 | −0.96 (15) | C11—C10—C12—O5 | −130.54 (13) |
C3—C1—C2—N3 | −176.90 (13) | C9—C10—C12—O5 | 107.10 (13) |
N1—C1—C2—C6 | 170.31 (13) | C10—N4—C13—O5 | −1.56 (17) |
C3—C1—C2—C6 | −5.6 (2) | C10—N4—C13—C14 | 177.70 (13) |
C4—O2—C3—O1 | −7.0 (2) | C12—O5—C13—N4 | −5.31 (17) |
C4—O2—C3—C1 | 170.88 (14) | C12—O5—C13—C14 | 175.35 (12) |
N1—C1—C3—O1 | −53.3 (2) | N4—C13—C14—C15 | −159.58 (16) |
C2—C1—C3—O1 | 121.89 (18) | O5—C13—C14—C15 | 19.7 (2) |
N1—C1—C3—O2 | 128.71 (14) | N4—C13—C14—C19 | 19.4 (2) |
C2—C1—C3—O2 | −56.09 (19) | O5—C13—C14—C19 | −161.28 (14) |
C3—O2—C4—C5 | −165.55 (16) | C19—C14—C15—C16 | −0.6 (3) |
C7—O4—C6—O3 | −0.8 (2) | C13—C14—C15—C16 | 178.45 (16) |
C7—O4—C6—C2 | 178.29 (13) | C14—C15—C16—C17 | 0.4 (3) |
N3—C2—C6—O3 | 158.83 (17) | C15—C16—C17—C18 | 0.3 (3) |
C1—C2—C6—O3 | −11.1 (2) | C16—C17—C18—C19 | −0.9 (3) |
N3—C2—C6—O4 | −20.2 (2) | C17—C18—C19—C14 | 0.7 (3) |
C1—C2—C6—O4 | 169.83 (13) | C15—C14—C19—C18 | 0.0 (3) |
C6—O4—C7—C8 | −174.17 (17) | C13—C14—C19—C18 | −179.03 (17) |
C1—N1—C9—C10 | −88.40 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7B···N3i | 0.97 | 2.59 | 3.454 (2) | 149 |
C11—H11A···O1ii | 0.96 | 2.56 | 3.392 (2) | 145 |
Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+3/2, z+1/2. |
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