N-But-oxy-carbonyl-5-oxo-l-proline ethyl ester.

The mol-ecular structure of the title compound, C12H19NO5, may be visualized as made up of two nearly perpendicular planes [dihedral angle = 87.39 (12)°] and its crystal structure is a good example of C-H⋯O inter-actions assuming significance in optimizing supra-molecular aggregation in crystals in a mol-ecule which is severely imbalanced in terms of donors to acceptor atoms. The pyrrolidine ring adopts a ((3) T 2) twist conformation with puckering parameters Q = 0.2630 (4) Å and ϕ = 59 (9)°. The crystal structure features R 2 (4)(10) and R 3 (4)(26) ring motifs formed by four weak C-H⋯O inter-actions, leading to supra-molecular sheets lying parallel to the bc plane.

Related literature

For general background, see: Holladay et al. (1991 ▶); Kayushina & Vainshtein (1966 ▶); Wu (2009 ▶). For the biological activity of proline derivatives, see: Hayashi et al. (2003 ▶); Nishikawa & Murakami (2005 ▶). For hydrogen bonding, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C12H19NO5

M = 257.28

Orthorhombic,

a = 26.6884 (13) Å

b = 5.7650 (3) Å

c = 8.7054 (4) Å

V = 1339.40 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.83 mm−1

T = 100 K

0.44 × 0.21 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.711, T max = 0.914

9641 measured reflections

2184 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.166

S = 1.09

2184 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007265/bx2436sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007265/bx2436Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007265/bx2436Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H19NO5	F(000) = 552
Mr = 257.28	Dx = 1.276 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2145 reflections
a = 26.6884 (13) Å	θ = 5.2–67.7°
b = 5.7650 (3) Å	µ = 0.83 mm−1
c = 8.7054 (4) Å	T = 100 K
V = 1339.40 (11) Å3	Block, colourless
Z = 4	0.44 × 0.21 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	2184 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 65.0°, θmin = 7.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −31→31
Tmin = 0.711, Tmax = 0.914	k = −5→6
9641 measured reflections	l = −10→10

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0688P)2 + 1.9721P] where P = (Fo2 + 2Fc2)/3
2184 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

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.

	x	y	z	Uiso*/Ueq
O1	0.90408 (10)	0.9206 (5)	0.6629 (3)	0.0370 (7)
O4	0.87203 (9)	0.6029 (5)	0.3651 (3)	0.0363 (6)
O3	0.95830 (10)	1.1864 (5)	0.2879 (3)	0.0385 (6)
O2	0.91287 (10)	0.5496 (5)	0.7415 (3)	0.0418 (7)
O5	0.88646 (10)	0.8660 (5)	0.1762 (3)	0.0390 (7)
N1	0.93969 (11)	0.8201 (6)	0.3819 (3)	0.0322 (7)
C5	0.96730 (14)	1.0270 (7)	0.3731 (4)	0.0336 (8)
C4	1.00831 (15)	1.0151 (7)	0.4918 (4)	0.0386 (9)
H4A	1.0015	1.1235	0.5774	0.046*
H4B	1.0411	1.0549	0.4456	0.046*
C3	1.00806 (15)	0.7635 (7)	0.5485 (4)	0.0378 (9)
H3A	1.0148	0.7561	0.6603	0.045*
H3B	1.0335	0.6700	0.4938	0.045*
C2	0.95504 (14)	0.6769 (7)	0.5120 (4)	0.0346 (8)
H2A	0.9563	0.5103	0.4803	0.042*
C1	0.92075 (14)	0.7041 (7)	0.6499 (4)	0.0362 (9)
C6	0.87505 (15)	0.9735 (8)	0.8004 (4)	0.0412 (9)
H6A	0.8760	1.1427	0.8195	0.049*
H6B	0.8904	0.8948	0.8898	0.049*
C7	0.82162 (16)	0.8971 (8)	0.7847 (5)	0.0473 (10)
H7A	0.8025	0.9492	0.8744	0.071*
H7B	0.8203	0.7276	0.7781	0.071*
H7C	0.8072	0.9647	0.6915	0.071*
C8	0.89734 (14)	0.7707 (7)	0.2939 (4)	0.0351 (9)
C9	0.82710 (14)	0.4960 (7)	0.2939 (5)	0.0414 (9)
C10	0.81499 (16)	0.3074 (8)	0.4085 (6)	0.0484 (11)
H10A	0.8427	0.1963	0.4126	0.073*
H10B	0.7843	0.2271	0.3769	0.073*
H10C	0.8101	0.3764	0.5102	0.073*
C11	0.78525 (15)	0.6769 (8)	0.2898 (6)	0.0510 (11)
H11A	0.7814	0.7463	0.3920	0.077*
H11B	0.7538	0.6023	0.2597	0.077*
H11C	0.7937	0.7981	0.2153	0.077*
C12	0.83972 (17)	0.3976 (8)	0.1365 (5)	0.0483 (11)
H12A	0.8695	0.2986	0.1444	0.072*
H12B	0.8464	0.5251	0.0650	0.072*
H12C	0.8114	0.3056	0.0987	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0497 (15)	0.0307 (15)	0.0307 (14)	−0.0008 (11)	0.0045 (11)	0.0004 (11)
O4	0.0413 (14)	0.0347 (15)	0.0327 (14)	−0.0024 (11)	−0.0049 (11)	0.0012 (11)
O3	0.0514 (15)	0.0343 (15)	0.0299 (13)	−0.0023 (12)	0.0013 (11)	0.0055 (13)
O2	0.0514 (16)	0.0403 (17)	0.0337 (14)	−0.0004 (12)	−0.0029 (12)	0.0086 (13)
O5	0.0558 (16)	0.0319 (15)	0.0292 (14)	0.0016 (12)	−0.0065 (11)	0.0035 (11)
N1	0.0416 (16)	0.0317 (17)	0.0233 (14)	0.0021 (13)	−0.0015 (13)	−0.0043 (14)
C5	0.043 (2)	0.033 (2)	0.0250 (17)	0.0001 (16)	0.0050 (15)	−0.0017 (17)
C4	0.044 (2)	0.042 (2)	0.0294 (19)	−0.0046 (18)	0.0010 (16)	−0.0040 (18)
C3	0.042 (2)	0.043 (2)	0.0288 (19)	0.0037 (17)	−0.0004 (15)	0.0043 (17)
C2	0.044 (2)	0.029 (2)	0.0311 (18)	0.0025 (16)	−0.0027 (15)	0.0054 (16)
C1	0.0379 (19)	0.041 (2)	0.0293 (19)	−0.0021 (16)	−0.0072 (15)	−0.0011 (18)
C6	0.051 (2)	0.045 (2)	0.0272 (18)	0.0005 (18)	0.0077 (17)	−0.0008 (18)
C7	0.052 (2)	0.046 (3)	0.044 (2)	0.0044 (19)	0.0069 (19)	−0.002 (2)
C8	0.041 (2)	0.030 (2)	0.034 (2)	0.0048 (15)	0.0007 (16)	0.0002 (16)
C9	0.041 (2)	0.034 (2)	0.048 (2)	−0.0004 (17)	−0.0083 (17)	−0.005 (2)
C10	0.048 (2)	0.037 (3)	0.061 (3)	−0.0058 (18)	−0.001 (2)	0.004 (2)
C11	0.044 (2)	0.040 (3)	0.069 (3)	0.0004 (18)	−0.011 (2)	−0.003 (3)
C12	0.064 (3)	0.037 (2)	0.044 (2)	−0.002 (2)	−0.015 (2)	−0.003 (2)

O1—C1	1.330 (5)	C6—C7	1.499 (6)
O1—C6	1.458 (4)	C6—H6A	0.9900
O4—C8	1.332 (5)	C6—H6B	0.9900
O4—C9	1.484 (5)	C7—H7A	0.9800
O3—C5	1.205 (5)	C7—H7B	0.9800
O2—C1	1.214 (5)	C7—H7C	0.9800
O5—C8	1.198 (5)	C9—C10	1.510 (6)
N1—C8	1.395 (5)	C9—C12	1.521 (6)
N1—C5	1.404 (5)	C9—C11	1.529 (6)
N1—C2	1.461 (5)	C10—H10A	0.9800
C5—C4	1.506 (5)	C10—H10B	0.9800
C4—C3	1.533 (6)	C10—H10C	0.9800
C4—H4A	0.9900	C11—H11A	0.9800
C4—H4B	0.9900	C11—H11B	0.9800
C3—C2	1.534 (5)	C11—H11C	0.9800
C3—H3A	0.9900	C12—H12A	0.9800
C3—H3B	0.9900	C12—H12B	0.9800
C2—C1	1.517 (5)	C12—H12C	0.9800
C2—H2A	1.0000
C1—O1—C6	116.4 (3)	H6A—C6—H6B	107.9
C8—O4—C9	121.1 (3)	C6—C7—H7A	109.5
C8—N1—C5	124.7 (3)	C6—C7—H7B	109.5
C8—N1—C2	122.5 (3)	H7A—C7—H7B	109.5
C5—N1—C2	112.0 (3)	C6—C7—H7C	109.5
O3—C5—N1	125.2 (3)	H7A—C7—H7C	109.5
O3—C5—C4	127.0 (4)	H7B—C7—H7C	109.5
N1—C5—C4	107.8 (3)	O5—C8—O4	127.4 (4)
C5—C4—C3	105.1 (3)	O5—C8—N1	124.9 (4)
C5—C4—H4A	110.7	O4—C8—N1	107.7 (3)
C3—C4—H4A	110.7	O4—C9—C10	101.3 (3)
C5—C4—H4B	110.7	O4—C9—C12	110.6 (3)
C3—C4—H4B	110.7	C10—C9—C12	111.9 (4)
H4A—C4—H4B	108.8	O4—C9—C11	108.5 (3)
C4—C3—C2	104.2 (3)	C10—C9—C11	110.5 (4)
C4—C3—H3A	110.9	C12—C9—C11	113.3 (4)
C2—C3—H3A	110.9	C9—C10—H10A	109.5
C4—C3—H3B	110.9	C9—C10—H10B	109.5
C2—C3—H3B	110.9	H10A—C10—H10B	109.5
H3A—C3—H3B	108.9	C9—C10—H10C	109.5
N1—C2—C1	112.7 (3)	H10A—C10—H10C	109.5
N1—C2—C3	103.6 (3)	H10B—C10—H10C	109.5
C1—C2—C3	111.0 (3)	C9—C11—H11A	109.5
N1—C2—H2A	109.8	C9—C11—H11B	109.5
C1—C2—H2A	109.8	H11A—C11—H11B	109.5
C3—C2—H2A	109.8	C9—C11—H11C	109.5
O2—C1—O1	125.1 (4)	H11A—C11—H11C	109.5
O2—C1—C2	123.3 (4)	H11B—C11—H11C	109.5
O1—C1—C2	111.5 (3)	C9—C12—H12A	109.5
O1—C6—C7	111.7 (3)	C9—C12—H12B	109.5
O1—C6—H6A	109.3	H12A—C12—H12B	109.5
C7—C6—H6A	109.3	C9—C12—H12C	109.5
O1—C6—H6B	109.3	H12A—C12—H12C	109.5
C7—C6—H6B	109.3	H12B—C12—H12C	109.5
C8—N1—C5—O3	−0.8 (6)	N1—C2—C1—O2	149.4 (4)
C2—N1—C5—O3	−171.0 (4)	C3—C2—C1—O2	−94.8 (4)
C8—N1—C5—C4	177.3 (3)	N1—C2—C1—O1	−35.4 (4)
C2—N1—C5—C4	7.1 (4)	C3—C2—C1—O1	80.3 (4)
O3—C5—C4—C3	−171.4 (4)	C1—O1—C6—C7	−81.1 (4)
N1—C5—C4—C3	10.6 (4)	C9—O4—C8—O5	5.8 (6)
C5—C4—C3—C2	−23.0 (4)	C9—O4—C8—N1	−174.7 (3)
C8—N1—C2—C1	−72.0 (4)	C5—N1—C8—O5	19.8 (6)
C5—N1—C2—C1	98.5 (4)	C2—N1—C8—O5	−170.9 (4)
C8—N1—C2—C3	167.9 (3)	C5—N1—C8—O4	−159.7 (3)
C5—N1—C2—C3	−21.6 (4)	C2—N1—C8—O4	9.5 (5)
C4—C3—C2—N1	26.7 (4)	C8—O4—C9—C10	175.3 (3)
C4—C3—C2—C1	−94.6 (4)	C8—O4—C9—C12	56.5 (5)
C6—O1—C1—O2	1.3 (5)	C8—O4—C9—C11	−68.4 (4)
C6—O1—C1—C2	−173.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3i	1.00	2.51	3.436 (5)	154
C3—H3B···O3ii	0.99	2.46	3.095 (5)	121
C6—H6B···O5iii	0.99	2.50	3.344 (5)	143
C12—H12A···O5i	0.98	2.55	3.327 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3i	1.00	2.51	3.436 (5)	154
C3—H3B⋯O3ii	0.99	2.46	3.095 (5)	121
C6—H6B⋯O5iii	0.99	2.50	3.344 (5)	143
C12—H12A⋯O5i	0.98	2.55	3.327 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) .