Ethyl 2-allyl-2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate

El Hafi, M.; Lahmidi, S.; Boulhaoua, M.; Essaghouani, A.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617012433

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 9| September 2017| x171243

https://doi.org/10.1107/S2414314617012433

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Ethyl 2-allyl-2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate

Mohamed El Hafi,^a ^* Sanae Lahmidi,^a Mohammed Boulhaoua,^a Abdelhanine Essaghouani,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: elhafi.mohamed1@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 25 August 2017; accepted 28 August 2017; online 5 September 2017)

In the title molecule, C₁₆H₂₀N₄O₂, the dihedral angle between the planes of the fused rings is 2.26 (8)°. In the crystal, [ $[\overline{2}]$ 10] chains of molecules linked by C—H⋯O and C—H⋯N hydrogen bonds arise, which are further linked by weak C—H⋯π interactions.

Keywords: crystal structure; triazolopyrimidine; alkylation; hydrogen bond.

CCDC reference: 1571230

Structure description

Triazolopyrimidine derivatives display various pharmacological properties, including anti-inflammatory (Ashour et al., 2013 ), anticancer (Hoffmann et al., 2017 ) and antibacterial (Mabkhot et al., 2016 ) activities. The present work is a continuation of our structural studies of triazolopyrimidine derivatives (Lahmidi et al., 2016 ) and reports the synthesis and structure of the title compound, ethyl 2-allyl-2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate (Fig. 1).

Figure 1
The title molecule, shown with 50% probability displacement ellipsoids.

The bicyclic unit is slightly nonplanar, as indicated by the dihedral angle of 2.26 (8)° between the planes of the five- and six-membered rings. In the crystal, molecules form centrosymmetric dimers through complementary C1—H1⋯O1ⁱ hydrogen bonds, which are connected into [ $[\overline{2}]$ 10] chains by C16—H16A⋯N4ⁱⁱ hydrogen bonds (Table 1 and Fig. 2). The chains are connected by C12—H12⋯Cg1ⁱⁱⁱ (Cg1 is the centroid of the C1/N3/C2/N1/N2 ring) interactions (Table 1 and Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.962 (14)	2.315 (14)	3.2388 (15)	160.7 (11)
C16—H16A⋯N4ⁱⁱ	0.976 (16)	2.610 (16)	3.4354 (18)	142.4 (12)
C12—H12⋯Cg1ⁱⁱⁱ	0.981 (15)	2.955 (15)	3.6559 (15)	129.3 (11)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Detail of the intermolecular interactions, with C—H⋯O and C—H⋯N hydrogen bonds shown as black dashed lines, while the C—H⋯π(ring) is shown as a green dashed line. [Symmetry codes: (i) −x + 1, −y + 1, −z + 2; (ii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; (iii) −x + $[{1\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ .]

Figure 3
The packing of the title compound, viewed along the c-axis direction, with intermolecular interactions depicted as in Fig. 2

Synthesis and crystallization

Allyl bromide (0.22 ml, 2.5 mmol), potassium carbonate (0.34 g, 2.5 mmol) and a catalytic quantity of tetra-n-butylammonium iodide were added to a solution of ethyl 2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)acetate (0.5 g, 2.3 mmol) in DMF (15 ml). The mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent removed under reduced pressure. The resulting residue was purified by column chromatography (EtOAc–hexane 1/9 v/v). The title compound was recrystallized from an ethanol solution at room temperature to yield colourless plates (yield 30%; m.p. 364–366 K).

Refinement

Crystal and refinement data are presented in Table 2. The H atoms were located in difference maps and their positions and U_iso(H) values were refined freely.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₄O₂
M_r	300.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.0937 (9), 13.4926 (12), 11.6936 (11)
β (°)	92.999 (1)
V (Å³)	1590.4 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.24 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.83, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	14774, 3914, 2819
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.03
No. of reflections	3914
No. of parameters	279
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.18
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1571230

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617012433/hb4166sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617012433/hb4166Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012433/hb4166Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617012433/hb4166Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2016).

Ethyl 2-allyl-2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate top

Crystal data top

C₁₆H₂₀N₄O₂	F(000) = 640
M_r = 300.36	D_x = 1.254 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0937 (9) Å	Cell parameters from 4361 reflections
b = 13.4926 (12) Å	θ = 2.3–27.5°
c = 11.6936 (11) Å	µ = 0.09 mm⁻¹
β = 92.999 (1)°	T = 100 K
V = 1590.4 (2) Å³	Plate, colourless
Z = 4	0.30 × 0.24 × 0.07 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3914 independent reflections
Radiation source: fine-focus sealed tube	2819 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.3°, θ_min = 2.3°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −17→17
T_min = 0.83, T_max = 0.99	l = −15→15
14774 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
3914 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.37418 (8)	0.59703 (6)	0.81629 (7)	0.0269 (2)
O2	0.52312 (8)	0.53189 (6)	0.70030 (7)	0.0237 (2)
N1	0.45281 (9)	0.32484 (7)	0.77637 (8)	0.0195 (2)
N2	0.47572 (10)	0.37149 (8)	0.87926 (8)	0.0231 (2)
N3	0.58922 (10)	0.22459 (8)	0.87571 (9)	0.0252 (3)
N4	0.51065 (10)	0.17365 (7)	0.68593 (9)	0.0230 (2)
C1	0.55721 (12)	0.30760 (9)	0.93342 (11)	0.0245 (3)
H1	0.5901 (13)	0.3219 (10)	1.0103 (12)	0.027 (4)*
C2	0.52088 (11)	0.23590 (9)	0.77578 (10)	0.0207 (3)
C3	0.43401 (12)	0.20285 (9)	0.59705 (11)	0.0226 (3)
C4	0.36816 (12)	0.29598 (9)	0.59266 (10)	0.0210 (3)
H4	0.3144 (12)	0.3147 (9)	0.5254 (11)	0.019 (3)*
C5	0.37784 (11)	0.35921 (8)	0.68375 (10)	0.0189 (3)
C6	0.41670 (16)	0.13343 (11)	0.49806 (12)	0.0309 (3)
H6A	0.343 (2)	0.0885 (15)	0.5148 (17)	0.068 (6)*
H6B	0.4950 (19)	0.0955 (13)	0.4883 (15)	0.057 (5)*
H6C	0.3894 (18)	0.1684 (13)	0.4266 (16)	0.057 (5)*
C7	0.31002 (11)	0.45886 (8)	0.69306 (10)	0.0198 (3)
C8	0.18878 (12)	0.44847 (9)	0.76874 (11)	0.0222 (3)
H8A	0.2226 (13)	0.4273 (10)	0.8461 (12)	0.023 (3)*
H8B	0.1481 (13)	0.5139 (10)	0.7775 (11)	0.026 (3)*
C9	0.08519 (13)	0.37797 (11)	0.72205 (11)	0.0292 (3)
H9	0.1090 (14)	0.3062 (11)	0.7130 (12)	0.036 (4)*
C10	−0.03729 (15)	0.40450 (14)	0.69308 (13)	0.0409 (4)
H10A	−0.1047 (16)	0.3565 (12)	0.6617 (14)	0.047 (5)*
H10B	−0.0668 (18)	0.4742 (14)	0.7006 (15)	0.058 (5)*
C11	0.26878 (13)	0.49788 (9)	0.57071 (10)	0.0219 (3)
H11A	0.2026 (14)	0.4522 (11)	0.5368 (12)	0.032 (4)*
H11B	0.3478 (13)	0.4967 (10)	0.5237 (12)	0.027 (4)*
C12	0.21439 (14)	0.60122 (10)	0.57129 (11)	0.0274 (3)
H12	0.1231 (15)	0.6095 (11)	0.5947 (12)	0.036 (4)*
C13	0.27982 (17)	0.67987 (11)	0.54030 (14)	0.0383 (4)
H13A	0.373 (2)	0.6753 (14)	0.5132 (16)	0.065 (6)*
H13B	0.2415 (16)	0.7449 (13)	0.5415 (14)	0.051 (5)*
C14	0.40517 (12)	0.53624 (8)	0.74715 (10)	0.0213 (3)
C15	0.62385 (14)	0.60166 (10)	0.74566 (13)	0.0290 (3)
H15A	0.5776 (15)	0.6664 (11)	0.7541 (12)	0.035 (4)*
H15B	0.6865 (14)	0.6049 (11)	0.6882 (13)	0.032 (4)*
C16	0.68866 (14)	0.56365 (12)	0.85544 (13)	0.0329 (3)
H16A	0.7608 (15)	0.6089 (11)	0.8776 (13)	0.038 (4)*
H16B	0.7315 (16)	0.4978 (13)	0.8408 (13)	0.041 (4)*
H16C	0.6263 (15)	0.5586 (11)	0.9181 (13)	0.039 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0307 (5)	0.0223 (5)	0.0272 (5)	0.0025 (4)	−0.0037 (4)	−0.0072 (4)
O2	0.0236 (4)	0.0226 (5)	0.0246 (5)	−0.0033 (3)	−0.0010 (4)	−0.0015 (3)
N1	0.0227 (5)	0.0183 (5)	0.0173 (5)	−0.0003 (4)	−0.0009 (4)	−0.0019 (4)
N2	0.0262 (5)	0.0244 (5)	0.0183 (5)	−0.0010 (4)	−0.0035 (4)	−0.0021 (4)
N3	0.0257 (6)	0.0244 (6)	0.0251 (6)	0.0010 (4)	−0.0025 (4)	0.0015 (4)
N4	0.0257 (5)	0.0197 (5)	0.0238 (6)	0.0005 (4)	0.0026 (4)	−0.0009 (4)
C1	0.0258 (6)	0.0266 (7)	0.0206 (7)	−0.0005 (5)	−0.0027 (5)	0.0013 (5)
C2	0.0198 (6)	0.0183 (6)	0.0240 (6)	0.0010 (5)	0.0018 (5)	0.0014 (5)
C3	0.0243 (6)	0.0204 (6)	0.0234 (6)	−0.0017 (5)	0.0048 (5)	−0.0018 (5)
C4	0.0235 (6)	0.0211 (6)	0.0183 (6)	−0.0009 (5)	0.0000 (5)	−0.0004 (5)
C5	0.0192 (6)	0.0200 (6)	0.0176 (6)	−0.0008 (4)	0.0013 (5)	0.0006 (5)
C6	0.0408 (8)	0.0251 (7)	0.0267 (7)	0.0039 (6)	0.0008 (6)	−0.0070 (6)
C7	0.0218 (6)	0.0189 (6)	0.0185 (6)	0.0015 (5)	−0.0021 (5)	−0.0022 (5)
C8	0.0238 (6)	0.0236 (7)	0.0190 (6)	0.0032 (5)	−0.0003 (5)	−0.0019 (5)
C9	0.0294 (7)	0.0353 (8)	0.0234 (7)	−0.0056 (6)	0.0054 (5)	−0.0044 (6)
C10	0.0302 (8)	0.0600 (11)	0.0319 (8)	−0.0114 (7)	−0.0046 (6)	0.0064 (7)
C11	0.0244 (6)	0.0226 (6)	0.0184 (6)	0.0017 (5)	−0.0020 (5)	−0.0011 (5)
C12	0.0316 (7)	0.0284 (7)	0.0217 (7)	0.0073 (6)	−0.0027 (5)	0.0004 (5)
C13	0.0447 (9)	0.0251 (8)	0.0441 (9)	0.0024 (7)	−0.0063 (7)	0.0061 (6)
C14	0.0252 (6)	0.0180 (6)	0.0204 (6)	0.0022 (5)	−0.0032 (5)	0.0010 (5)
C15	0.0272 (7)	0.0262 (7)	0.0332 (8)	−0.0088 (6)	−0.0008 (6)	0.0000 (6)
C16	0.0257 (7)	0.0413 (9)	0.0312 (8)	−0.0088 (6)	−0.0025 (6)	−0.0015 (6)

Geometric parameters (Å, º) top

O1—C14	1.2044 (14)	C7—C11	1.5605 (16)
O2—C14	1.3377 (15)	C8—C9	1.4954 (18)
O2—C15	1.4645 (15)	C8—H8A	0.992 (14)
N1—N2	1.3668 (14)	C8—H8B	0.981 (14)
N1—C5	1.3693 (15)	C9—C10	1.314 (2)
N1—C2	1.3830 (15)	C9—H9	1.004 (15)
N2—C1	1.3290 (16)	C10—H10A	0.995 (17)
N3—C2	1.3342 (15)	C10—H10B	0.992 (18)
N3—C1	1.3553 (16)	C11—C12	1.4987 (18)
N4—C3	1.3228 (16)	C11—H11A	0.977 (14)
N4—C2	1.3449 (16)	C11—H11B	0.992 (15)
C1—H1	0.962 (14)	C12—C13	1.311 (2)
C3—C4	1.4211 (17)	C12—H12	0.981 (15)
C3—C6	1.4922 (18)	C13—H13A	1.01 (2)
C4—C5	1.3642 (16)	C13—H13B	0.960 (17)
C4—H4	0.965 (13)	C15—C16	1.500 (2)
C5—C7	1.5154 (16)	C15—H15A	0.998 (15)
C6—H6A	0.99 (2)	C15—H15B	0.947 (15)
C6—H6B	0.954 (19)	C16—H16A	0.976 (16)
C6—H6C	0.986 (18)	C16—H16B	1.007 (17)
C7—C14	1.5326 (16)	C16—H16C	0.993 (16)
C7—C8	1.5536 (17)

C14—O2—C15	116.06 (10)	C9—C8—H8B	108.8 (8)
N2—N1—C5	126.97 (10)	C7—C8—H8B	109.0 (8)
N2—N1—C2	110.05 (9)	H8A—C8—H8B	106.8 (11)
C5—N1—C2	122.96 (10)	C10—C9—C8	123.45 (15)
C1—N2—N1	101.11 (10)	C10—C9—H9	117.5 (8)
C2—N3—C1	102.46 (10)	C8—C9—H9	119.0 (8)
C3—N4—C2	116.47 (10)	C9—C10—H10A	122.2 (9)
N2—C1—N3	117.16 (11)	C9—C10—H10B	121.2 (10)
N2—C1—H1	119.4 (8)	H10A—C10—H10B	116.6 (14)
N3—C1—H1	123.5 (8)	C12—C11—C7	112.95 (10)
N3—C2—N4	128.89 (11)	C12—C11—H11A	110.2 (8)
N3—C2—N1	109.21 (10)	C7—C11—H11A	107.6 (8)
N4—C2—N1	121.86 (11)	C12—C11—H11B	108.8 (8)
N4—C3—C4	123.02 (11)	C7—C11—H11B	108.6 (8)
N4—C3—C6	117.55 (11)	H11A—C11—H11B	108.6 (11)
C4—C3—C6	119.43 (11)	C13—C12—C11	124.19 (14)
C5—C4—C3	120.69 (11)	C13—C12—H12	118.6 (9)
C5—C4—H4	119.1 (7)	C11—C12—H12	117.1 (9)
C3—C4—H4	120.2 (8)	C12—C13—H13A	121.9 (11)
C4—C5—N1	114.82 (10)	C12—C13—H13B	121.8 (10)
C4—C5—C7	126.65 (11)	H13A—C13—H13B	116.3 (14)
N1—C5—C7	118.47 (10)	O1—C14—O2	124.94 (11)
C3—C6—H6A	106.9 (11)	O1—C14—C7	124.18 (11)
C3—C6—H6B	111.5 (11)	O2—C14—C7	110.67 (10)
H6A—C6—H6B	109.3 (15)	O2—C15—C16	110.70 (11)
C3—C6—H6C	111.9 (10)	O2—C15—H15A	106.2 (8)
H6A—C6—H6C	106.4 (15)	C16—C15—H15A	113.6 (8)
H6B—C6—H6C	110.7 (14)	O2—C15—H15B	104.4 (9)
C5—C7—C14	111.00 (9)	C16—C15—H15B	110.2 (9)
C5—C7—C8	109.46 (10)	H15A—C15—H15B	111.3 (12)
C14—C7—C8	108.77 (9)	C15—C16—H16A	107.4 (9)
C5—C7—C11	109.47 (9)	C15—C16—H16B	109.2 (9)
C14—C7—C11	106.26 (10)	H16A—C16—H16B	106.1 (13)
C8—C7—C11	111.86 (9)	C15—C16—H16C	112.9 (9)
C9—C8—C7	113.95 (10)	H16A—C16—H16C	109.9 (12)
C9—C8—H8A	110.5 (8)	H16B—C16—H16C	111.1 (13)
C7—C8—H8A	107.6 (8)

C5—N1—N2—C1	−177.62 (11)	N1—C5—C7—C14	45.52 (14)
C2—N1—N2—C1	0.51 (12)	C4—C5—C7—C8	102.45 (13)
N1—N2—C1—N3	0.09 (14)	N1—C5—C7—C8	−74.56 (13)
C2—N3—C1—N2	−0.64 (14)	C4—C5—C7—C11	−20.49 (16)
C1—N3—C2—N4	−177.09 (12)	N1—C5—C7—C11	162.50 (10)
C1—N3—C2—N1	0.91 (12)	C5—C7—C8—C9	−61.13 (13)
C3—N4—C2—N3	179.07 (12)	C14—C7—C8—C9	177.43 (11)
C3—N4—C2—N1	1.30 (17)	C11—C7—C8—C9	60.38 (14)
N2—N1—C2—N3	−0.95 (13)	C7—C8—C9—C10	−118.44 (14)
C5—N1—C2—N3	177.27 (10)	C5—C7—C11—C12	−173.66 (10)
N2—N1—C2—N4	177.22 (10)	C14—C7—C11—C12	−53.73 (14)
C5—N1—C2—N4	−4.56 (18)	C8—C7—C11—C12	64.83 (14)
C2—N4—C3—C4	2.01 (17)	C7—C11—C12—C13	104.71 (15)
C2—N4—C3—C6	−177.65 (11)	C15—O2—C14—O1	5.68 (17)
N4—C3—C4—C5	−2.33 (18)	C15—O2—C14—C7	−179.35 (9)
C6—C3—C4—C5	177.32 (12)	C5—C7—C14—O1	−139.28 (12)
C3—C4—C5—N1	−0.75 (17)	C8—C7—C14—O1	−18.80 (16)
C3—C4—C5—C7	−177.85 (11)	C11—C7—C14—O1	101.79 (13)
N2—N1—C5—C4	−178.06 (11)	C5—C7—C14—O2	45.70 (13)
C2—N1—C5—C4	4.03 (16)	C8—C7—C14—O2	166.19 (9)
N2—N1—C5—C7	−0.71 (17)	C11—C7—C14—O2	−73.23 (11)
C2—N1—C5—C7	−178.61 (10)	C14—O2—C15—C16	80.88 (14)
C4—C5—C7—C14	−137.48 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.962 (14)	2.315 (14)	3.2388 (15)	160.7 (11)
C16—H16A···N4ⁱⁱ	0.976 (16)	2.610 (16)	3.4354 (18)	142.4 (12)
C12—H12···Cg1ⁱⁱⁱ	0.981 (15)	2.955 (15)	3.6559 (15)	129.3 (11)

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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IUCrDATA

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Volume 2| Part 9| September 2017| x171243

https://doi.org/10.1107/S2414314617012433

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-allyl-2-(5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)pent-4-enoate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds