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

Lahmidi, S.; El Hafi, M.; Moussaif, A.; Benchidmi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618012804

organic compounds

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ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181280

https://doi.org/10.1107/S2414314618012804

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

Sanae Lahmidi,^a ^* Mohamed El Hafi,^a Ahmed Moussaif,^b Mohammed Benchidmi,^a El Mokhtar Essassi ^a and Joel T. Mague ^c

^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, ^bNational Center of Energy Sciences and Nuclear Techniques, Rabat, Morocco, and ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: lahmidi_sanae@yahoo.fr

Edited by S. Parkin, University of Kentucky, USA (Received 30 August 2018; accepted 11 September 2018; online 21 September 2018)

In the title molecule, C₁₃H₁₆N₄O₂, the fused triazolopyrimidine ring system is planar. In the crystal, inversion-related C—H⋯O hydrogen bonds form dimers that are linked into chains extending along the a-axis direction by inversion-related C—H⋯π(ring) interactions.

Keywords: crystal structure; triazole; pyrimidine; hydrogen bond; C—H⋯π(ring) interaction.

CCDC reference: 1866951

Structure description

Among the various classes of nitrogen-containing heterocyclic compounds, triazolopyrimidine derivatives display a broad spectrum of biological activities, including anti-inflammatory (Ashour et al., 2013 ), anticancer (Hoffmann et al., 2017 ) and antibacterial properties (Mabkhot et al., 2016 ). The present work is a continuation of the investigation of the triazolopyrimidine derivatives published by our team (El Otmani et al., 2002 ; Lahmidi et al., 2016 ).

The fused triazolopyrimidine ring system is planar to within 0.011 (1) Å (r.m.s. deviation = 0.001) while the pent-4-enoate unit is nearly orthogonal to this plane as indicated by the C3—C4—C7—H7 torsion angle of −6.5 (9)° (Fig. 1). In the crystal, inversion-related C5—H5⋯O1 hydrogen bonds form dimers which are connected into chains running along the a-axis direction by inversion-related C10—H10B⋯Cg1 interactions, where Cg1 is the centroid of the C5/N2/C6/N4/N3 ring (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5/N2/C6/N4/N3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	1.000 (12)	2.532 (12)	3.4147 (19)	147.1 (9)
C10—H10B⋯Cg1ⁱⁱ	0.962 (17)	2.747 (18)	3.657 (3)	143.9 (13)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Figure 1
The title molecule with labelling scheme and 50% probability ellipsoids. For the sake of clarity, disorder of methyl group C1 is not shown.

Figure 2
A portion of one chain viewed along the c-axis direction. C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions are shown, respectively, by black and green dashed lines.

Synthesis and crystallization

To a solution of ethyl 2-(5-methyl1,2,4-triazolo[1,5-a]pyrimidin-7-yl)acetate (1 g, 4.5 mmol) was added potassium hydroxide (0.3 g, 5.4 mmol) in acetone (20 ml). After 10 min of stirring, allyl bromide (0.94 ml, 10 mmol) was added dropwise. Upon disappearance of the starting material as indicated by TLC, the resulting mixture was evaporated. The crude material was dissolved with EtOAc (50 ml), washed with water and brine, dried over MgSO₄ and the solvent was evaporated in vacuo. The resulting residue was purified by column chromatography (EtOAc/hexane 2:8). The title compound was recrystallized from ethanol at room temperature giving colourless crystals (yield: 55%; m.p. 350–352 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl group based on C1 is rotationally disordered over two sites in approximately equal amounts.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₄O₂
M_r	260.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	9.069 (5), 13.319 (7), 11.851 (7)
β (°)	112.161 (7)
V (Å³)	1325.8 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.97, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	24464, 3472, 2810
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.115, 1.13
No. of reflections	3472
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1866951

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618012804/pk4019sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2414314618012804/pk4019Isup3.cdx

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618012804/pk4019Isup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618012804/pk4019Isup4.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: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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

Crystal data top

C₁₃H₁₆N₄O₂	F(000) = 552
M_r = 260.30	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.069 (5) Å	Cell parameters from 9961 reflections
b = 13.319 (7) Å	θ = 2.4–29.0°
c = 11.851 (7) Å	µ = 0.09 mm⁻¹
β = 112.161 (7)°	T = 120 K
V = 1325.8 (13) Å³	Block, colourless
Z = 4	0.28 × 0.26 × 0.23 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3472 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.1°, θ_min = 2.4°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −17→18
T_min = 0.97, T_max = 0.98	l = −15→16
24464 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)] = 0.039	Hydrogen site location: mixed
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0711P)² + 0.0365P] where P = (F_o² + 2F_c²)/3
3472 reflections	(Δ/σ)_max = 0.014
225 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 deg. in omega, colllected at phi = 0.00, 90.00 and 180.00 deg. and 2 sets of 800 frames, each of width 0.45 deg in phi, collected at omega = -30.00 and 210.00 deg. The scan time was 20 sec/frame.

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. The methyl group based on C1 is rotationally disordered over two sites in approximately equal amounts. The pertinent H-atoms were included as riding contributions with an AFIX 127 instruction.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.56233 (10)	0.23682 (6)	0.58967 (7)	0.0344 (2)
O2	0.64639 (8)	0.31664 (5)	0.77039 (6)	0.02493 (18)
N1	0.32526 (10)	0.55771 (6)	0.86016 (8)	0.02209 (19)
N2	0.41823 (10)	0.63445 (6)	0.71457 (8)	0.0239 (2)
N3	0.43853 (9)	0.48972 (6)	0.61662 (7)	0.02074 (19)
N4	0.38663 (9)	0.46935 (5)	0.70826 (7)	0.01672 (18)
C1	0.23525 (14)	0.46863 (8)	0.99890 (11)	0.0300 (2)
H1A	0.272897	0.529471	1.047853	0.045*	0.5
H1B	0.277616	0.409356	1.049848	0.045*	0.5
H1C	0.118632	0.466814	0.966951	0.045*	0.5
H1D	0.173199	0.407623	0.995248	0.045*	0.5
H1E	0.168480	0.527738	0.993253	0.045*	0.5
H1F	0.327464	0.470281	1.076151	0.045*	0.5
C2	0.29106 (11)	0.46900 (7)	0.89531 (9)	0.0209 (2)
C3	0.30429 (11)	0.37708 (7)	0.83846 (9)	0.0196 (2)
H3	0.2757 (14)	0.3120 (9)	0.8652 (11)	0.027 (3)*
C4	0.35412 (11)	0.37704 (6)	0.74367 (8)	0.0176 (2)
C5	0.45486 (12)	0.58899 (7)	0.62636 (9)	0.0231 (2)
H5	0.4937 (15)	0.6272 (8)	0.5704 (11)	0.025 (3)*
C6	0.37471 (11)	0.55701 (7)	0.76663 (9)	0.0188 (2)
C7	0.37022 (12)	0.28654 (7)	0.67375 (9)	0.0199 (2)
H7	0.3497 (13)	0.2254 (9)	0.7171 (11)	0.023 (3)*
C8	0.24441 (12)	0.28407 (8)	0.54242 (9)	0.0230 (2)
H8A	0.2732 (14)	0.3346 (9)	0.4912 (11)	0.025 (3)*
H8B	0.2499 (14)	0.2163 (9)	0.5127 (11)	0.027 (3)*
C9	0.08070 (12)	0.30597 (8)	0.53659 (10)	0.0258 (2)
H9	0.0388 (16)	0.2663 (10)	0.5872 (12)	0.032 (3)*
C10	−0.01043 (15)	0.37689 (9)	0.46752 (11)	0.0348 (3)
H10A	0.0325 (18)	0.4190 (11)	0.4135 (14)	0.046 (4)*
H10B	−0.1163 (18)	0.3876 (10)	0.4648 (14)	0.046 (4)*
C11	0.53584 (12)	0.27690 (7)	0.67105 (9)	0.0227 (2)
C12	0.80941 (13)	0.31869 (10)	0.77462 (11)	0.0321 (3)
H12A	0.8249 (16)	0.2611 (10)	0.7309 (13)	0.035 (3)*
H12B	0.8722 (16)	0.3147 (9)	0.8617 (13)	0.033 (3)*
C13	0.84073 (14)	0.41573 (11)	0.72326 (12)	0.0384 (3)
H13A	0.8213 (18)	0.4730 (11)	0.7691 (15)	0.048 (4)*
H13B	0.9544 (19)	0.4119 (11)	0.7269 (14)	0.048 (4)*
H13C	0.7697 (18)	0.4231 (11)	0.6367 (14)	0.047 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0358 (4)	0.0395 (4)	0.0304 (4)	0.0086 (3)	0.0153 (3)	−0.0084 (3)
O2	0.0220 (4)	0.0319 (4)	0.0213 (4)	0.0054 (3)	0.0086 (3)	0.0003 (3)
N1	0.0237 (4)	0.0214 (4)	0.0231 (4)	−0.0003 (3)	0.0111 (3)	−0.0032 (3)
N2	0.0272 (4)	0.0193 (4)	0.0269 (5)	−0.0022 (3)	0.0123 (4)	0.0002 (3)
N3	0.0231 (4)	0.0225 (4)	0.0194 (4)	−0.0009 (3)	0.0112 (3)	0.0030 (3)
N4	0.0178 (4)	0.0173 (4)	0.0165 (4)	0.0000 (3)	0.0081 (3)	−0.0003 (3)
C1	0.0361 (6)	0.0337 (6)	0.0273 (6)	−0.0027 (5)	0.0201 (5)	−0.0037 (4)
C2	0.0201 (4)	0.0230 (5)	0.0202 (5)	0.0004 (4)	0.0083 (4)	−0.0017 (3)
C3	0.0205 (4)	0.0186 (4)	0.0203 (5)	0.0001 (3)	0.0085 (4)	0.0010 (3)
C4	0.0165 (4)	0.0165 (4)	0.0188 (5)	0.0010 (3)	0.0057 (3)	0.0011 (3)
C5	0.0245 (5)	0.0217 (5)	0.0242 (5)	−0.0022 (4)	0.0104 (4)	0.0022 (4)
C6	0.0181 (4)	0.0167 (4)	0.0206 (5)	0.0005 (3)	0.0062 (4)	−0.0015 (3)
C7	0.0252 (5)	0.0159 (4)	0.0199 (5)	0.0010 (4)	0.0099 (4)	−0.0001 (3)
C8	0.0284 (5)	0.0207 (5)	0.0197 (5)	−0.0022 (4)	0.0089 (4)	−0.0022 (4)
C9	0.0268 (5)	0.0254 (5)	0.0240 (5)	−0.0053 (4)	0.0081 (4)	−0.0045 (4)
C10	0.0317 (6)	0.0358 (6)	0.0316 (6)	0.0027 (5)	0.0060 (5)	−0.0027 (5)
C11	0.0265 (5)	0.0204 (4)	0.0219 (5)	0.0064 (4)	0.0100 (4)	0.0018 (4)
C12	0.0211 (5)	0.0476 (7)	0.0277 (6)	0.0110 (5)	0.0094 (4)	0.0019 (5)
C13	0.0250 (6)	0.0630 (9)	0.0291 (6)	0.0004 (6)	0.0123 (5)	0.0060 (6)

Geometric parameters (Å, º) top

O1—C11	1.2032 (13)	C3—H3	0.990 (12)
O2—C11	1.3345 (13)	C4—C7	1.5008 (14)
O2—C12	1.4605 (15)	C5—H5	1.000 (12)
N1—C2	1.3279 (14)	C7—C11	1.5198 (16)
N1—C6	1.3434 (14)	C7—C8	1.5445 (15)
N2—C6	1.3357 (13)	C7—H7	1.017 (12)
N2—C5	1.3535 (14)	C8—C9	1.4889 (16)
N3—C5	1.3306 (15)	C8—H8A	1.005 (12)
N3—N4	1.3638 (12)	C8—H8B	0.977 (12)
N4—C4	1.3667 (13)	C9—C10	1.3172 (17)
N4—C6	1.3820 (13)	C9—H9	0.978 (14)
C1—C2	1.4940 (16)	C10—H10A	1.032 (15)
C1—H1A	0.9800	C10—H10B	0.959 (15)
C1—H1B	0.9800	C12—C13	1.501 (2)
C1—H1C	0.9800	C12—H12A	0.965 (14)
C1—H1D	0.9800	C12—H12B	0.974 (14)
C1—H1E	0.9800	C13—H13A	0.990 (16)
C1—H1F	0.9800	C13—H13B	1.017 (16)
C2—C3	1.4241 (14)	C13—H13C	0.989 (15)
C3—C4	1.3599 (14)

C11—O2—C12	116.85 (9)	N3—C5—H5	120.3 (7)
C2—N1—C6	116.29 (8)	N2—C5—H5	122.4 (7)
C6—N2—C5	102.29 (9)	N2—C6—N1	128.65 (9)
C5—N3—N4	100.91 (8)	N2—C6—N4	109.18 (9)
N3—N4—C4	127.07 (8)	N1—C6—N4	122.17 (9)
N3—N4—C6	110.26 (8)	C4—C7—C11	112.47 (8)
C4—N4—C6	122.65 (9)	C4—C7—C8	112.63 (8)
C2—C1—H1A	109.5	C11—C7—C8	109.71 (9)
C2—C1—H1B	109.5	C4—C7—H7	106.9 (7)
H1A—C1—H1B	109.5	C11—C7—H7	108.3 (6)
C2—C1—H1C	109.5	C8—C7—H7	106.6 (7)
H1A—C1—H1C	109.5	C9—C8—C7	112.78 (9)
H1B—C1—H1C	109.5	C9—C8—H8A	108.8 (7)
C2—C1—H1D	109.5	C7—C8—H8A	109.5 (7)
H1A—C1—H1D	141.1	C9—C8—H8B	110.5 (7)
H1B—C1—H1D	56.3	C7—C8—H8B	105.3 (7)
H1C—C1—H1D	56.3	H8A—C8—H8B	110.0 (10)
C2—C1—H1E	109.5	C10—C9—C8	123.39 (11)
H1A—C1—H1E	56.3	C10—C9—H9	118.1 (8)
H1B—C1—H1E	141.1	C8—C9—H9	118.5 (8)
H1C—C1—H1E	56.3	C9—C10—H10A	118.7 (8)
H1D—C1—H1E	109.5	C9—C10—H10B	120.9 (9)
C2—C1—H1F	109.5	H10A—C10—H10B	120.4 (12)
H1A—C1—H1F	56.3	O1—C11—O2	124.92 (10)
H1B—C1—H1F	56.3	O1—C11—C7	123.51 (9)
H1C—C1—H1F	141.1	O2—C11—C7	111.56 (8)
H1D—C1—H1F	109.5	O2—C12—C13	110.25 (9)
H1E—C1—H1F	109.5	O2—C12—H12A	108.5 (8)
N1—C2—C3	123.03 (10)	C13—C12—H12A	112.2 (8)
N1—C2—C1	116.90 (9)	O2—C12—H12B	102.4 (8)
C3—C2—C1	120.07 (9)	C13—C12—H12B	110.6 (8)
C4—C3—C2	120.31 (9)	H12A—C12—H12B	112.3 (11)
C4—C3—H3	118.2 (7)	C12—C13—H13A	110.0 (9)
C2—C3—H3	121.5 (7)	C12—C13—H13B	106.5 (8)
C3—C4—N4	115.52 (8)	H13A—C13—H13B	113.7 (12)
C3—C4—C7	126.04 (9)	C12—C13—H13C	110.9 (9)
N4—C4—C7	118.41 (9)	H13A—C13—H13C	108.1 (12)
N3—C5—N2	117.37 (9)	H13B—C13—H13C	107.6 (12)

C5—N3—N4—C4	−177.92 (9)	N3—N4—C6—N2	−0.07 (10)
C5—N3—N4—C6	0.17 (10)	C4—N4—C6—N2	178.12 (8)
C6—N1—C2—C3	−0.25 (14)	N3—N4—C6—N1	179.66 (8)
C6—N1—C2—C1	−179.75 (9)	C4—N4—C6—N1	−2.16 (14)
N1—C2—C3—C4	0.13 (15)	C3—C4—C7—C11	−125.28 (10)
C1—C2—C3—C4	179.61 (9)	N4—C4—C7—C11	57.08 (11)
C2—C3—C4—N4	−0.91 (14)	C3—C4—C7—C8	110.12 (12)
C2—C3—C4—C7	−178.61 (8)	N4—C4—C7—C8	−67.52 (12)
N3—N4—C4—C3	179.76 (8)	C4—C7—C8—C9	−46.69 (12)
C6—N4—C4—C3	1.90 (13)	C11—C7—C8—C9	−172.79 (8)
N3—N4—C4—C7	−2.35 (13)	C7—C8—C9—C10	125.75 (11)
C6—N4—C4—C7	179.78 (8)	C12—O2—C11—O1	5.43 (15)
N4—N3—C5—N2	−0.23 (11)	C12—O2—C11—C7	−175.66 (8)
C6—N2—C5—N3	0.19 (12)	C4—C7—C11—O1	−151.70 (10)
C5—N2—C6—N1	−179.76 (10)	C8—C7—C11—O1	−25.51 (13)
C5—N2—C6—N4	−0.07 (10)	C4—C7—C11—O2	29.37 (11)
C2—N1—C6—N2	−179.11 (9)	C8—C7—C11—O2	155.55 (8)
C2—N1—C6—N4	1.22 (14)	C11—O2—C12—C13	91.48 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C5/N2/C6/N4/N3 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	1.000 (12)	2.532 (12)	3.4147 (19)	147.1 (9)
C10—H10B···Cg1ⁱⁱ	0.962 (17)	2.747 (18)	3.657 (3)	143.9 (13)

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

Acknowledgements

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

References

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IUCrDATA

ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181280

https://doi.org/10.1107/S2414314618012804

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

Ethyl 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