Crystal structure of 1-benzyl-2-hy­droxy-5-oxopyrrolidin-3-yl acetate

Caracelli, I.; Zukerman-Schpector, J.; Stefani, H.A.; Ali, B.; Tiekink, E.R.T.

doi:10.1107/S2056989015013353

organic compounds

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ISSN: 2056-9890

Volume 71| Part 8| August 2015| Pages o582-o583

https://doi.org/10.1107/S2056989015013353

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Crystal structure of 1-benzyl-2-hydroxy-5-oxopyrrolidin-3-yl acetate

Ignez Caracelli,^a ^* Julio Zukerman-Schpector,^b Hélio A. Stefani,^c Bakhat Ali ^c and Edward R. T. Tiekink ^d

^aDepartmento de Física, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^bDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, ^cDepartamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900 São Paulo-SP, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: julio@power.ufscar.br

Edited by P. C. Healy, Griffith University, Australia (Received 7 July 2015; accepted 12 July 2015; online 17 July 2015)

In the title compound, C₁₃H₁₅NO₄, the oxopyrrolidin-3-yl ring has an envelope conformation, with the C atom bearing the acetate group being the flap. The acetate and phenyl groups are inclined with respect to the central ring, forming dihedral angles of 50.20 (12) and 87.40 (9)°, respectively, with the least-squares plane through the ring. The dihedral angle between the acetate group and the phenyl ring is 63.22 (8)°, indicating a twisted conformation in the molecule. In the crystal, supramolecular chains along the b axis are formed by (hydroxy)O—H⋯O(ring carbonyl) hydrogen bonds. The chains are consolidated into the three-dimensional architecture by C—H⋯O interactions.

Keywords: crystal structure; oxopyrrolidin-3-yl; hydrogen bonding; conformation.

CCDC reference: 1412190

1. Related literature

For the synthesis of symmetrical 1,4-dioxanes, including the title compound, via Lewis-acid-catalysed N-acyliminium ion cyclodimerization, and for a related structure, see: Ali et al. (2015 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₅NO₄
M_r = 249.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 26.504 (2) Å
b = 6.3668 (5) Å
c = 7.6040 (6) Å
V = 1283.14 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.56 × 0.40 × 0.36 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.673, T_max = 0.745
4917 measured reflections
2246 independent reflections
2087 reflections with I > 2σ(I)
R_int = 0.014

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.06
2246 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4ⁱ	0.82	1.86	2.671 (2)	170
C5—H5A⋯O2ⁱⁱ	0.97	2.49	3.452 (3)	170
C5—H5B⋯O3ⁱⁱⁱ	0.97	2.51	3.437 (3)	160
C12—H12⋯O2^iv	0.93	2.54	3.421 (4)	158
Symmetry code: (i) x, y-1, z; (ii) x, y+1, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1412190

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015013353/hg5452sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013353/hg5452Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015013353/hg5452Isup3.cml

checkCIF report

Related literature top

For the synthesis of symmetrical 1,4-dioxanes, including the title compound, via Lewis-acid-catalysed N-acyliminium ion cyclodimerization, and for a related structure, see: Ali et al. (2015).

Experimental top

The title compound was prepared as described in the literature (Ali et al., 2015) and crystals were obtained from the slow evaporation of its methanol solution.

Structure description top

For the synthesis of symmetrical 1,4-dioxanes, including the title compound, via Lewis-acid-catalysed N-acyliminium ion cyclodimerization, and for a related structure, see: Ali et al. (2015).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the supramolecular chain along the b axis mediated by O—H···O hydrogen bonding shown as orange dashed lines.
	Fig. 3. A view in projection down the b axis of the unit-cell contents. The O—H···O and C—H···O interactions shown as orange and blue dashed lines, respectively.

1-Benzyl-2-hydroxy-5-oxopyrrolidin-3-yl acetate top

Crystal data top

C₁₃H₁₅NO₄	D_x = 1.290 Mg m⁻³
M_r = 249.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3310 reflections
a = 26.504 (2) Å	θ = 2.8–25.3°
b = 6.3668 (5) Å	µ = 0.10 mm⁻¹
c = 7.6040 (6) Å	T = 293 K
V = 1283.14 (17) Å³	Block, colourless
Z = 4	0.56 × 0.40 × 0.36 mm
F(000) = 528

Data collection top

Bruker APEXII CCD diffractometer	2087 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.014
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 25.3°, θ_min = 2.8°
T_min = 0.673, T_max = 0.745	h = −31→26
4917 measured reflections	k = −5→7
2246 independent reflections	l = −9→7

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0507P)² + 0.1542P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2246 reflections	Δρ_max = 0.10 e Å⁻³
165 parameters	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₃H₁₅NO₄	V = 1283.14 (17) Å³
M_r = 249.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 26.504 (2) Å	µ = 0.10 mm⁻¹
b = 6.3668 (5) Å	T = 293 K
c = 7.6040 (6) Å	0.56 × 0.40 × 0.36 mm

Data collection top

Bruker APEXII CCD diffractometer	2246 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2087 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.745	R_int = 0.014
4917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	Δρ_max = 0.10 e Å⁻³
2246 reflections	Δρ_min = −0.18 e Å⁻³
165 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.04798 (6)	0.8021 (3)	0.0393 (2)	0.0590 (4)
O2	0.10250 (7)	0.5494 (3)	−0.0319 (3)	0.0797 (6)
O3	0.05817 (6)	0.6595 (2)	0.3698 (2)	0.0626 (5)
H3O	0.0678	0.5486	0.4131	0.094*
O4	0.09632 (7)	1.2919 (2)	0.4745 (3)	0.0736 (5)
N1	0.11194 (6)	0.9434 (3)	0.4315 (3)	0.0528 (5)
C1	0.08701 (8)	0.8984 (3)	0.1433 (3)	0.0540 (5)
H1	0.1175	0.9160	0.0717	0.065*
C2	0.09990 (8)	0.7747 (3)	0.3111 (3)	0.0497 (5)
H2	0.1291	0.6831	0.2924	0.060*
C4	0.09357 (8)	1.1311 (3)	0.3844 (3)	0.0547 (5)
C5	0.06905 (10)	1.1103 (4)	0.2074 (4)	0.0614 (6)
H5A	0.0799	1.2216	0.1289	0.074*
H5B	0.0326	1.1139	0.2173	0.074*
C6	0.06079 (10)	0.6229 (4)	−0.0410 (3)	0.0594 (6)
C7	0.01803 (12)	0.5271 (5)	−0.1385 (4)	0.0792 (8)
H7A	0.0041	0.4141	−0.0706	0.119*
H7B	0.0299	0.4738	−0.2492	0.119*
H7C	−0.0075	0.6314	−0.1589	0.119*
C8	0.13462 (9)	0.9012 (4)	0.6024 (3)	0.0605 (6)
H8A	0.1153	0.7925	0.6613	0.073*
H8B	0.1328	1.0272	0.6738	0.073*
C9	0.18888 (8)	0.8323 (4)	0.5891 (3)	0.0525 (5)
C10	0.20395 (10)	0.6420 (4)	0.6570 (4)	0.0707 (7)
H10	0.1803	0.5528	0.7079	0.085*
C11	0.25400 (13)	0.5831 (6)	0.6500 (5)	0.0973 (11)
H11	0.2643	0.4563	0.6991	0.117*
C12	0.28864 (12)	0.7121 (8)	0.5703 (5)	0.1080 (14)
H12	0.3222	0.6711	0.5627	0.130*
C13	0.27379 (11)	0.9002 (9)	0.5023 (4)	0.1085 (14)
H13	0.2974	0.9877	0.4491	0.130*
C14	0.22412 (10)	0.9614 (6)	0.5120 (4)	0.0799 (9)
H14	0.2143	1.0905	0.4662	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0530 (9)	0.0571 (9)	0.0668 (10)	0.0025 (7)	−0.0072 (7)	0.0012 (8)
O2	0.0751 (12)	0.0781 (12)	0.0861 (13)	0.0164 (10)	0.0149 (10)	0.0015 (11)
O3	0.0543 (8)	0.0431 (8)	0.0902 (12)	−0.0007 (7)	0.0038 (8)	0.0173 (8)
O4	0.0824 (12)	0.0420 (8)	0.0963 (13)	−0.0005 (8)	−0.0194 (10)	0.0025 (9)
N1	0.0482 (9)	0.0437 (9)	0.0664 (11)	0.0037 (8)	−0.0082 (9)	0.0093 (8)
C1	0.0446 (11)	0.0507 (12)	0.0667 (13)	−0.0019 (9)	−0.0034 (9)	0.0113 (11)
C2	0.0414 (10)	0.0410 (10)	0.0667 (13)	0.0048 (9)	0.0002 (9)	0.0066 (10)
C4	0.0470 (11)	0.0385 (10)	0.0785 (15)	−0.0031 (9)	−0.0072 (10)	0.0097 (11)
C5	0.0593 (13)	0.0433 (11)	0.0817 (16)	0.0010 (10)	−0.0149 (12)	0.0136 (11)
C6	0.0685 (15)	0.0562 (12)	0.0535 (12)	0.0004 (12)	0.0092 (11)	0.0130 (11)
C7	0.103 (2)	0.0685 (16)	0.0663 (15)	−0.0102 (16)	−0.0066 (16)	−0.0010 (13)
C8	0.0590 (13)	0.0645 (14)	0.0578 (12)	0.0100 (11)	−0.0006 (10)	0.0109 (11)
C9	0.0502 (11)	0.0596 (13)	0.0478 (10)	−0.0003 (10)	−0.0082 (9)	0.0043 (11)
C10	0.0658 (15)	0.0616 (14)	0.0847 (17)	0.0089 (12)	−0.0054 (13)	0.0060 (15)
C11	0.080 (2)	0.099 (2)	0.113 (3)	0.038 (2)	−0.021 (2)	−0.009 (2)
C12	0.0561 (16)	0.185 (4)	0.083 (2)	0.029 (2)	−0.0068 (16)	−0.022 (3)
C13	0.0540 (16)	0.197 (4)	0.0745 (19)	−0.027 (2)	−0.0063 (14)	0.025 (3)
C14	0.0660 (16)	0.103 (2)	0.0712 (16)	−0.0153 (15)	−0.0117 (13)	0.0294 (17)

Geometric parameters (Å, º) top

O1—C6	1.338 (3)	C7—H7A	0.9600
O1—C1	1.439 (3)	C7—H7B	0.9600
O2—C6	1.202 (3)	C7—H7C	0.9600
O3—C2	1.400 (3)	C8—C9	1.507 (3)
O3—H3O	0.8200	C8—H8A	0.9700
O4—C4	1.234 (3)	C8—H8B	0.9700
N1—C4	1.339 (3)	C9—C14	1.375 (4)
N1—C2	1.447 (3)	C9—C10	1.376 (4)
N1—C8	1.457 (3)	C10—C11	1.380 (4)
C1—C5	1.512 (3)	C10—H10	0.9300
C1—C2	1.538 (3)	C11—C12	1.373 (5)
C1—H1	0.9800	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.363 (6)
C4—C5	1.501 (4)	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.375 (5)
C5—H5B	0.9700	C13—H13	0.9300
C6—C7	1.486 (4)	C14—H14	0.9300

C6—O1—C1	115.57 (18)	C6—C7—H7B	109.5
C2—O3—H3O	109.5	H7A—C7—H7B	109.5
C4—N1—C2	114.41 (18)	C6—C7—H7C	109.5
C4—N1—C8	123.6 (2)	H7A—C7—H7C	109.5
C2—N1—C8	121.22 (18)	H7B—C7—H7C	109.5
O1—C1—C5	109.34 (18)	N1—C8—C9	112.81 (19)
O1—C1—C2	113.42 (17)	N1—C8—H8A	109.0
C5—C1—C2	105.0 (2)	C9—C8—H8A	109.0
O1—C1—H1	109.6	N1—C8—H8B	109.0
C5—C1—H1	109.6	C9—C8—H8B	109.0
C2—C1—H1	109.6	H8A—C8—H8B	107.8
O3—C2—N1	111.19 (18)	C14—C9—C10	119.3 (2)
O3—C2—C1	110.93 (17)	C14—C9—C8	120.2 (2)
N1—C2—C1	101.18 (17)	C10—C9—C8	120.5 (2)
O3—C2—H2	111.1	C9—C10—C11	120.3 (3)
N1—C2—H2	111.1	C9—C10—H10	119.9
C1—C2—H2	111.1	C11—C10—H10	119.9
O4—C4—N1	124.8 (2)	C12—C11—C10	119.8 (3)
O4—C4—C5	126.6 (2)	C12—C11—H11	120.1
N1—C4—C5	108.6 (2)	C10—C11—H11	120.1
C4—C5—C1	103.40 (18)	C13—C12—C11	120.0 (3)
C4—C5—H5A	111.1	C13—C12—H12	120.0
C1—C5—H5A	111.1	C11—C12—H12	120.0
C4—C5—H5B	111.1	C12—C13—C14	120.3 (3)
C1—C5—H5B	111.1	C12—C13—H13	119.8
H5A—C5—H5B	109.0	C14—C13—H13	119.8
O2—C6—O1	122.6 (2)	C13—C14—C9	120.3 (3)
O2—C6—C7	124.8 (3)	C13—C14—H14	119.9
O1—C6—C7	112.6 (2)	C9—C14—H14	119.9
C6—C7—H7A	109.5

C6—O1—C1—C5	173.36 (18)	O1—C1—C5—C4	146.44 (18)
C6—O1—C1—C2	−69.8 (2)	C2—C1—C5—C4	24.4 (2)
C4—N1—C2—O3	−97.9 (2)	C1—O1—C6—O2	−2.1 (3)
C8—N1—C2—O3	72.3 (2)	C1—O1—C6—C7	177.2 (2)
C4—N1—C2—C1	20.0 (2)	C4—N1—C8—C9	−119.2 (2)
C8—N1—C2—C1	−169.84 (18)	C2—N1—C8—C9	71.6 (3)
O1—C1—C2—O3	−27.8 (3)	N1—C8—C9—C14	59.4 (3)
C5—C1—C2—O3	91.5 (2)	N1—C8—C9—C10	−121.9 (2)
O1—C1—C2—N1	−145.88 (18)	C14—C9—C10—C11	1.0 (4)
C5—C1—C2—N1	−26.6 (2)	C8—C9—C10—C11	−177.7 (3)
C2—N1—C4—O4	174.5 (2)	C9—C10—C11—C12	−1.9 (5)
C8—N1—C4—O4	4.6 (4)	C10—C11—C12—C13	1.6 (6)
C2—N1—C4—C5	−4.9 (3)	C11—C12—C13—C14	−0.4 (6)
C8—N1—C4—C5	−174.8 (2)	C12—C13—C14—C9	−0.6 (5)
O4—C4—C5—C1	167.7 (2)	C10—C9—C14—C13	0.3 (4)
N1—C4—C5—C1	−13.0 (3)	C8—C9—C14—C13	179.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4ⁱ	0.82	1.86	2.671 (2)	170
C5—H5A···O2ⁱⁱ	0.97	2.49	3.452 (3)	170
C5—H5B···O3ⁱⁱⁱ	0.97	2.51	3.437 (3)	160
C12—H12···O2^iv	0.93	2.54	3.421 (4)	158

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4ⁱ	0.82	1.86	2.671 (2)	170
C5—H5A···O2ⁱⁱ	0.97	2.49	3.452 (3)	170
C5—H5B···O3ⁱⁱⁱ	0.97	2.51	3.437 (3)	160
C12—H12···O2^iv	0.93	2.54	3.421 (4)	158

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

Acknowledgements

We thank Professor Regina H. A. Santos from IQSC–USP for the X-ray data collection. The Brazilian agencies CNPq (305626/2013-2 to JZS, 306121/2013-2 to IC and 308320/2010-7 to HAS), FAPESP (2012/17954-4 and 2013/21925-2) and CAPES are acknowledged for financial support.

References

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