(Z)-Ethyl 3-(2,6-diisopropyl­anilino)but-2-enoate

Amézquita-Valencia, M.; Hernández-Ortega, S.; Suárez-Ortiz, G.A.; Cabrera, A.

doi:10.1107/S1600536810003260

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o500

doi:10.1107/S1600536810003260

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(Z)-Ethyl 3-(2,6-diisopropylanilino)but-2-enoate

Manuel Amézquita-Valencia,^a ^* Simón Hernández-Ortega,^a G. Alejandra Suárez-Ortiz ^a and Armando Cabrera ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
^*Correspondence e-mail: simonho@unam.mx, majo00@yahoo.com

(Received 1 December 2009; accepted 26 January 2010; online 3 February 2010)

The title compound, C₁₈H₂₇NO₂, crystallizes as the enamine form with Z geometry. The β-enaminoester fragment forms a dihedral angle of 87.5 (1)° with the isopropylphenyl frame. The structure exhibits an intramolecular N—H⋯O hydrogen bond. In addition, in the crystal, molecules are linked by a centrosymmetric intermolecular N—H⋯O hydrogen bond.

Related literature

For methods used in the preparation of β-enaminoketones and β-enaminoesters, see: Zhang & Yang (2009 ); Bartoli et al. (2004 ); Braibante et al. (2006 ). These compounds are used the preparation of key intermediates of pharmaceutical products (Michael et al., 1999 ), aminoacids (Palmieri & Cimmerelli, 1996 ), peptides and alkaloids (David et al., 1999 ). For our work on the synthesis of enaminoesters, see: Amézquita-Valencia et al. (2009 ).

Experimental

Crystal data

C₁₈H₂₇NO₂
M_r = 289.41
Triclinic, $[P \overline 1]$
a = 8.4750 (17) Å
b = 8.8995 (18) Å
c = 11.956 (2) Å
α = 94.901 (3)°
β = 91.801 (3)°
γ = 101.255 (4)°
V = 880.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.29 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
7319 measured reflections
3233 independent reflections
1574 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.085
S = 0.84
3233 reflections
199 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Selected Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.89 (1)	2.02 (1)	2.7402 (18)	137 (1)
N1—H1⋯O1ⁱ	0.89 (1)	2.68 (1)	3.3371 (18)	132 (1)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003260/gw2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003260/gw2075Isup2.hkl

checkCIF report

Comment top

Several methods have been carried out in the β-enaminoketones and β-enaminoesters preparations, for instances; catalysis by silica-supported antimony (III) chloride (Zhang & Yang, 2009), the use of Lewis acids (Bartoli, et al. 2004) solid acids such as montmorillonite K10 (Braibante, et al. 2006). Is necessary to improve this reaction, due to the named compounds are important precursors in organic synthesis, these are particularly useful as they can be further transformed to key intermediates of several pharmaceutical products (Michael et al., 1999). They have been utilized for the preparation of different important aminoacids (Palmieri et al., 1996), peptides and alkaloids (David et al., 1999). In continuation of our work in enaminoesters synthesis (Amézquita-Valencia, et al. 2009), we describe the structure of title compound (I) obtained using a Mexican bentonitic clay as catalist.

The structure with numbering scheme of the title compound is shown in fig. 1. The 2,6-diisopropylphenyl substituent is almost perpendicular to the β-enaminoester function (dihedral angle 87.5°), similar to described in ethyl 3-(2,6-dimethylphenylamino)but-2-enoate (Amézquita-Valencia, et al. 2009). A strong intramolecular N—H···O hydrogen bond is present in the structure, in addition, the molecules are linked by centrosymmetric intermolecular N—H···O hydrogen bond, the symmetry code is 1-x, -y 1-z, fig. 2.

Related literature top

For methods used in the preparation of β-enaminoketones and β-enaminoesters, see: Zhang & Yang (2009); Bartoli et al. (2004); Braibante et al. (2006). These compounds are used the preparation of key intermediates of pharmaceutical products (Michael et al., 1999), aminoacids (Palmieri et al., 1996), peptides and alkaloids (David et al., 1999). For our work on the synthesis of enaminoesters, see: Amézquita-Valencia et al. (2009).

Experimental top

Compound (I) was obtained following the procedure described in Amézquita-Valencia, et al. 2009. The product recrystallized from methanol. Yield: 92%, M.p. 326.3°

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The Molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms bonded to C omitted. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The centrosymmetric intermolecular N—H···O hydrogen bonding network in dashes lines. symmetry code 1-x, -y, 1-z.

(Z)-Ethyl 3-(2,6-diisopropylanilino)but-2-enoate top

Crystal data top

C₁₈H₂₇NO₂	Z = 2
M_r = 289.41	F(000) = 316
Triclinic, P1	D_x = 1.092 Mg m⁻³
Hall symbol: -P 1	Melting point: 326.3(2) K
a = 8.4750 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8995 (18) Å	Cell parameters from 1942 reflections
c = 11.956 (2) Å	θ = 2.5–24.1°
α = 94.901 (3)°	µ = 0.07 mm⁻¹
β = 91.801 (3)°	T = 298 K
γ = 101.255 (4)°	Prism, colorless
V = 880.1 (3) Å³	0.29 × 0.21 × 0.05 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.052
Graphite monochromator	θ_max = 25.4°, θ_min = 1.7°
Detector resolution: 0.83 pixels mm^-1	h = −10→10
ω scans	k = −10→10
7319 measured reflections	l = −14→14
3233 independent 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.11 e Å⁻³
1 restraint	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₁₈H₂₇NO₂	γ = 101.255 (4)°
M_r = 289.41	V = 880.1 (3) Å³
Triclinic, P1	Z = 2
a = 8.4750 (17) Å	Mo Kα radiation
b = 8.8995 (18) Å	µ = 0.07 mm⁻¹
c = 11.956 (2) Å	T = 298 K
α = 94.901 (3)°	0.29 × 0.21 × 0.05 mm
β = 91.801 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1574 reflections with I > 2σ(I)
7319 measured reflections	R_int = 0.052
3233 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	Δρ_max = 0.11 e Å⁻³
3233 reflections	Δρ_min = −0.10 e Å⁻³
199 parameters

Special details top

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 > σ(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	0.40766 (16)	0.15127 (14)	0.48653 (10)	0.0730 (4)
O2	0.30098 (15)	0.36079 (13)	0.46776 (9)	0.0683 (4)
N1	0.49463 (18)	0.01679 (16)	0.28928 (11)	0.0554 (4)
H1	0.4882 (18)	0.0192 (18)	0.3638 (8)	0.066*
C1	0.3661 (2)	0.2415 (2)	0.42624 (15)	0.0556 (5)
C2	0.3774 (2)	0.23743 (19)	0.30792 (14)	0.0574 (5)
H2	0.3404	0.3129	0.2713	0.069*
C3	0.4383 (2)	0.1311 (2)	0.24509 (14)	0.0521 (5)
C4	0.4449 (2)	0.1348 (2)	0.12035 (14)	0.0821 (7)
H4A	0.5552	0.1526	0.0999	0.123*
H4B	0.3952	0.2161	0.0974	0.123*
H4C	0.3885	0.0382	0.0838	0.123*
C5	0.5595 (2)	−0.1002 (2)	0.22757 (13)	0.0508 (5)
C6	0.7234 (2)	−0.0729 (2)	0.20876 (14)	0.0579 (5)
C7	0.7848 (2)	−0.1914 (3)	0.15333 (15)	0.0697 (6)
H7	0.8937	−0.1763	0.1392	0.084*
C8	0.6859 (3)	−0.3301 (3)	0.11939 (15)	0.0710 (6)
H8	0.7291	−0.4091	0.0842	0.085*
C9	0.5242 (3)	−0.3537 (2)	0.13675 (14)	0.0638 (5)
H9	0.4591	−0.4480	0.1118	0.077*
C10	0.4557 (2)	−0.2397 (2)	0.19079 (13)	0.0529 (5)
C11	0.8341 (2)	0.0779 (2)	0.24878 (18)	0.0793 (6)
H11	0.7657	0.1534	0.2650	0.095*
C12	0.9507 (3)	0.1411 (3)	0.1612 (2)	0.1274 (9)
H12A	1.0269	0.0753	0.1486	0.191*
H12B	1.0068	0.2428	0.1879	0.191*
H12C	0.8915	0.1448	0.0920	0.191*
C13	0.9264 (3)	0.0662 (3)	0.35821 (18)	0.1140 (8)
H13A	0.8516	0.0412	0.4157	0.171*
H13B	0.9972	0.1628	0.3807	0.171*
H13C	0.9884	−0.0129	0.3471	0.171*
C14	0.2780 (2)	−0.2639 (2)	0.21149 (15)	0.0665 (5)
H14	0.2455	−0.1650	0.2053	0.080*
C15	0.2454 (2)	−0.3071 (2)	0.33083 (17)	0.0971 (7)
H15A	0.2766	−0.4035	0.3403	0.146*
H15B	0.1326	−0.3164	0.3431	0.146*
H15C	0.3064	−0.2286	0.3840	0.146*
C16	0.1727 (2)	−0.3808 (2)	0.12593 (19)	0.1022 (8)
H16A	0.1915	−0.3503	0.0516	0.153*
H16B	0.0614	−0.3855	0.1412	0.153*
H16C	0.1988	−0.4803	0.1311	0.153*
C17	0.2874 (3)	0.3794 (2)	0.58714 (14)	0.0862 (7)
H17A	0.3930	0.3940	0.6249	0.103*
H17B	0.2202	0.2884	0.6120	0.103*
C18	0.2146 (2)	0.5158 (2)	0.61480 (15)	0.0817 (6)
H18A	0.2811	0.6051	0.5891	0.123*
H18B	0.2064	0.5312	0.6947	0.123*
H18C	0.1092	0.4994	0.5785	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1105 (11)	0.0678 (9)	0.0517 (8)	0.0418 (8)	0.0065 (7)	0.0118 (7)
O2	0.1025 (11)	0.0614 (8)	0.0497 (8)	0.0382 (8)	0.0095 (7)	0.0023 (6)
N1	0.0797 (11)	0.0503 (9)	0.0418 (8)	0.0262 (8)	0.0075 (8)	0.0038 (8)
C1	0.0659 (14)	0.0490 (12)	0.0539 (12)	0.0173 (11)	0.0035 (10)	0.0014 (10)
C2	0.0800 (14)	0.0495 (11)	0.0487 (11)	0.0265 (10)	0.0032 (10)	0.0070 (9)
C3	0.0637 (13)	0.0487 (11)	0.0461 (11)	0.0158 (10)	0.0014 (9)	0.0067 (9)
C4	0.1282 (19)	0.0817 (15)	0.0491 (11)	0.0482 (14)	0.0115 (11)	0.0131 (11)
C5	0.0670 (14)	0.0497 (12)	0.0405 (10)	0.0222 (11)	0.0045 (10)	0.0052 (9)
C6	0.0666 (15)	0.0558 (13)	0.0546 (11)	0.0179 (12)	0.0060 (10)	0.0089 (10)
C7	0.0696 (15)	0.0803 (15)	0.0657 (13)	0.0283 (14)	0.0127 (11)	0.0091 (12)
C8	0.0917 (18)	0.0764 (16)	0.0537 (12)	0.0419 (14)	0.0057 (12)	−0.0036 (11)
C9	0.0837 (16)	0.0548 (12)	0.0541 (12)	0.0210 (12)	−0.0033 (11)	−0.0027 (10)
C10	0.0703 (15)	0.0498 (12)	0.0429 (10)	0.0222 (11)	0.0012 (10)	0.0050 (9)
C11	0.0711 (15)	0.0695 (15)	0.0960 (17)	0.0116 (13)	0.0051 (13)	0.0055 (13)
C12	0.112 (2)	0.124 (2)	0.139 (2)	−0.0138 (17)	0.0189 (18)	0.0496 (18)
C13	0.117 (2)	0.1073 (19)	0.0989 (18)	−0.0166 (16)	−0.0228 (16)	0.0004 (15)
C14	0.0711 (15)	0.0559 (13)	0.0741 (14)	0.0173 (11)	0.0021 (11)	0.0060 (11)
C15	0.0893 (18)	0.1064 (18)	0.0986 (17)	0.0148 (14)	0.0304 (14)	0.0286 (15)
C16	0.0800 (17)	0.0877 (17)	0.132 (2)	0.0130 (14)	−0.0184 (15)	−0.0127 (15)
C17	0.137 (2)	0.0852 (15)	0.0495 (12)	0.0540 (15)	0.0167 (12)	0.0017 (11)
C18	0.1002 (17)	0.0771 (15)	0.0726 (14)	0.0309 (13)	0.0199 (12)	−0.0032 (11)

Geometric parameters (Å, º) top

O1—C1	1.2173 (18)	C11—C13	1.525 (3)
O2—C1	1.3543 (18)	C11—C12	1.529 (2)
O2—C17	1.4337 (18)	C11—H11	0.9800
N1—C3	1.3439 (19)	C12—H12A	0.9600
N1—C5	1.4310 (19)	C12—H12B	0.9600
N1—H1	0.894 (8)	C12—H12C	0.9600
C1—C2	1.419 (2)	C13—H13A	0.9600
C2—C3	1.350 (2)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.497 (2)	C14—C16	1.525 (2)
C4—H4A	0.9600	C14—C15	1.529 (2)
C4—H4B	0.9600	C14—H14	0.9800
C4—H4C	0.9600	C15—H15A	0.9600
C5—C6	1.392 (2)	C15—H15B	0.9600
C5—C10	1.402 (2)	C15—H15C	0.9600
C6—C7	1.392 (2)	C16—H16A	0.9600
C6—C11	1.510 (2)	C16—H16B	0.9600
C7—C8	1.371 (3)	C16—H16C	0.9600
C7—H7	0.9300	C17—C18	1.483 (2)
C8—C9	1.370 (2)	C17—H17A	0.9700
C8—H8	0.9300	C17—H17B	0.9700
C9—C10	1.388 (2)	C18—H18A	0.9600
C9—H9	0.9300	C18—H18B	0.9600
C10—C14	1.510 (2)	C18—H18C	0.9600

C1—O2—C17	116.95 (14)	C11—C12—H12A	109.5
C3—N1—C5	125.68 (14)	C11—C12—H12B	109.5
C3—N1—H1	113.3 (10)	H12A—C12—H12B	109.5
C5—N1—H1	121.1 (10)	C11—C12—H12C	109.5
O1—C1—O2	121.97 (16)	H12A—C12—H12C	109.5
O1—C1—C2	126.24 (17)	H12B—C12—H12C	109.5
O2—C1—C2	111.79 (16)	C11—C13—H13A	109.5
C3—C2—C1	124.19 (16)	C11—C13—H13B	109.5
C3—C2—H2	117.9	H13A—C13—H13B	109.5
C1—C2—H2	117.9	C11—C13—H13C	109.5
N1—C3—C2	122.83 (15)	H13A—C13—H13C	109.5
N1—C3—C4	116.49 (15)	H13B—C13—H13C	109.5
C2—C3—C4	120.68 (15)	C10—C14—C16	113.93 (16)
C3—C4—H4A	109.5	C10—C14—C15	111.14 (15)
C3—C4—H4B	109.5	C16—C14—C15	110.36 (17)
H4A—C4—H4B	109.5	C10—C14—H14	107.0
C3—C4—H4C	109.5	C16—C14—H14	107.0
H4A—C4—H4C	109.5	C15—C14—H14	107.0
H4B—C4—H4C	109.5	C14—C15—H15A	109.5
C6—C5—C10	122.50 (16)	C14—C15—H15B	109.5
C6—C5—N1	118.98 (17)	H15A—C15—H15B	109.5
C10—C5—N1	118.49 (17)	C14—C15—H15C	109.5
C7—C6—C5	117.78 (18)	H15A—C15—H15C	109.5
C7—C6—C11	120.22 (19)	H15B—C15—H15C	109.5
C5—C6—C11	121.99 (17)	C14—C16—H16A	109.5
C8—C7—C6	120.58 (19)	C14—C16—H16B	109.5
C8—C7—H7	119.7	H16A—C16—H16B	109.5
C6—C7—H7	119.7	C14—C16—H16C	109.5
C9—C8—C7	120.76 (18)	H16A—C16—H16C	109.5
C9—C8—H8	119.6	H16B—C16—H16C	109.5
C7—C8—H8	119.6	O2—C17—C18	108.30 (15)
C8—C9—C10	121.37 (19)	O2—C17—H17A	110.0
C8—C9—H9	119.3	C18—C17—H17A	110.0
C10—C9—H9	119.3	O2—C17—H17B	110.0
C9—C10—C5	116.97 (17)	C18—C17—H17B	110.0
C9—C10—C14	122.14 (18)	H17A—C17—H17B	108.4
C5—C10—C14	120.88 (16)	C17—C18—H18A	109.5
C6—C11—C13	111.31 (17)	C17—C18—H18B	109.5
C6—C11—C12	113.78 (18)	H18A—C18—H18B	109.5
C13—C11—C12	110.29 (19)	C17—C18—H18C	109.5
C6—C11—H11	107.0	H18A—C18—H18C	109.5
C13—C11—H11	107.0	H18B—C18—H18C	109.5
C12—C11—H11	107.0

C17—O2—C1—O1	1.9 (2)	C7—C8—C9—C10	−1.2 (3)
C17—O2—C1—C2	−178.36 (16)	C8—C9—C10—C5	−0.6 (2)
O1—C1—C2—C3	−0.6 (3)	C8—C9—C10—C14	−179.51 (16)
O2—C1—C2—C3	179.68 (17)	C6—C5—C10—C9	1.9 (2)
C5—N1—C3—C2	179.47 (17)	N1—C5—C10—C9	−176.47 (13)
C5—N1—C3—C4	0.0 (3)	C6—C5—C10—C14	−179.16 (14)
C1—C2—C3—N1	0.2 (3)	N1—C5—C10—C14	2.5 (2)
C1—C2—C3—C4	179.67 (17)	C7—C6—C11—C13	−79.3 (2)
C3—N1—C5—C6	88.8 (2)	C5—C6—C11—C13	99.3 (2)
C3—N1—C5—C10	−92.8 (2)	C7—C6—C11—C12	46.0 (2)
C10—C5—C6—C7	−1.4 (2)	C5—C6—C11—C12	−135.40 (19)
N1—C5—C6—C7	176.92 (14)	C9—C10—C14—C16	−27.7 (2)
C10—C5—C6—C11	179.97 (15)	C5—C10—C14—C16	153.41 (16)
N1—C5—C6—C11	−1.7 (2)	C9—C10—C14—C15	97.75 (19)
C5—C6—C7—C8	−0.4 (2)	C5—C10—C14—C15	−81.16 (19)
C11—C6—C7—C8	178.25 (17)	C1—O2—C17—C18	179.70 (16)
C6—C7—C8—C9	1.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.89 (1)	2.02 (1)	2.7402 (18)	137 (1)
N1—H1···O1ⁱ	0.89 (1)	2.68 (1)	3.3371 (18)	132 (1)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₇NO₂
M_r	289.41
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.4750 (17), 8.8995 (18), 11.956 (2)
α, β, γ (°)	94.901 (3), 91.801 (3), 101.255 (4)
V (Å³)	880.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.29 × 0.21 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7319, 3233, 1574
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.085, 0.84
No. of reflections	3233
No. of parameters	199
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.10

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

O1—C1	1.2173 (18)	N1—C5	1.4310 (19)
O2—C1	1.3543 (18)	C1—C2	1.419 (2)
N1—C3	1.3439 (19)	C2—C3	1.350 (2)

C3—N1—C5	125.68 (14)	C3—C2—C1	124.19 (16)
O1—C1—C2	126.24 (17)	N1—C3—C2	122.83 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.894 (8)	2.020 (12)	2.7402 (18)	136.8 (13)
N1—H1···O1ⁱ	0.894 (8)	2.677 (13)	3.3371 (18)	131.5 (12)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

MAV and AC thank DGAPA–UNAM for financial support (PAPIIT IN203209) and CONACyT (Fellowship 229448).

References

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