5-Ethoxy-5-(1-hydroxy­ethyl)-1-methyl­pyrrolidin-2-one

In the title compound, C₉H₁₇NO₃, the pyrrolidine ring is almost planar, in contrast with the classical envelope conformation observed in other pyrrolidine-containing derivatives. The enantiomers are joined into a centrosymmetric dimer by complementary intermolecular O—H...O hydrogen bonds between the hydroxyl and carbonyl groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.130
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

5-Ethoxy-5-(1-hydroxyethyl)-1-methylpyrrolidin-2-one

Crystal data

C9H17NO3	F(000) = 408
Mr = 187.24	Dx = 1.203 Mg m^−3
Monoclinic, P21/c	Melting point: 394(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.188 (2) Å	Cell parameters from 848 reflections
b = 17.363 (5) Å	θ = 2.4–24.8°
c = 8.297 (2) Å	µ = 0.09 mm^−1
β = 93.267 (5)°	T = 293 K
V = 1033.8 (5) Å^3	Block, colourless
Z = 4	0.20 × 0.14 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2122 independent reflections
Radiation source: fine-focus sealed tube	1362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.971, Tmax = 0.991	k = −21→18
5897 measured reflections	l = −10→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.2892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2122 reflections	Δρmax = 0.15 e Å^−3
126 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2056 (2)	0.57381 (9)	0.60819 (19)	0.0498 (5)
O1	0.2865 (2)	0.46519 (10)	0.4763 (2)	0.0739 (5)
O2	0.29844 (19)	0.67954 (7)	0.77324 (17)	0.0524 (4)
O3	−0.0972 (2)	0.55630 (10)	0.8151 (2)	0.0749 (5)
H3	−0.152 (5)	0.5484 (19)	0.715 (4)	0.130 (13)*
C1	0.2812 (3)	0.50390 (13)	0.5994 (3)	0.0531 (5)
C2	0.3587 (4)	0.48100 (13)	0.7625 (3)	0.0663 (6)
H2A	0.4930	0.4753	0.7629	0.080*
H2B	0.3052	0.4325	0.7951	0.080*
C3	0.3078 (3)	0.54442 (12)	0.8739 (3)	0.0582 (6)
H3A	0.4188	0.5653	0.9298	0.070*
H3B	0.2257	0.5251	0.9535	0.070*
C4	0.2092 (3)	0.60679 (11)	0.7703 (2)	0.0461 (5)
C5	0.0125 (3)	0.62414 (13)	0.8213 (3)	0.0568 (6)
H5	−0.0452	0.6623	0.7472	0.068*
C6	0.0112 (4)	0.65467 (16)	0.9921 (3)	0.0816 (8)
H6A	−0.1119	0.6721	1.0129	0.122*
H6B	0.0971	0.6969	1.0050	0.122*
H6C	0.0476	0.6144	1.0668	0.122*
C7	0.4881 (3)	0.68104 (13)	0.7303 (3)	0.0655 (6)
H7A	0.4998	0.6557	0.6271	0.079*
H7B	0.5664	0.6542	0.8111	0.079*
C8	0.5469 (4)	0.76259 (15)	0.7201 (4)	0.0861 (9)
H8A	0.4659	0.7891	0.6426	0.129*
H8B	0.6726	0.7650	0.6872	0.129*
H8C	0.5401	0.7865	0.8239	0.129*
C9	0.1338 (4)	0.61587 (15)	0.4667 (3)	0.0708 (7)
H9A	0.1657	0.5890	0.3710	0.106*
H9B	0.1874	0.6665	0.4671	0.106*
H9C	0.0007	0.6199	0.4684	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0568 (11)	0.0475 (10)	0.0453 (10)	−0.0024 (8)	0.0038 (7)	0.0021 (8)
O1	0.0671 (11)	0.0794 (12)	0.0759 (11)	−0.0046 (8)	0.0091 (8)	−0.0334 (9)
O2	0.0479 (8)	0.0432 (8)	0.0675 (9)	−0.0040 (6)	0.0153 (6)	−0.0037 (6)
O3	0.0698 (11)	0.0886 (13)	0.0669 (12)	−0.0333 (9)	0.0085 (9)	0.0059 (9)
C1	0.0457 (12)	0.0515 (13)	0.0629 (14)	−0.0087 (10)	0.0114 (9)	−0.0104 (11)
C2	0.0701 (15)	0.0581 (14)	0.0708 (16)	0.0127 (12)	0.0059 (12)	0.0048 (12)
C3	0.0659 (15)	0.0550 (13)	0.0536 (13)	−0.0019 (11)	0.0031 (10)	0.0085 (10)
C4	0.0506 (12)	0.0434 (11)	0.0445 (11)	−0.0043 (9)	0.0053 (9)	0.0004 (9)
C5	0.0492 (13)	0.0617 (14)	0.0606 (13)	−0.0039 (10)	0.0117 (10)	0.0037 (11)
C6	0.0679 (16)	0.097 (2)	0.0825 (18)	−0.0064 (14)	0.0308 (13)	−0.0241 (15)
C7	0.0530 (13)	0.0651 (15)	0.0800 (16)	−0.0083 (11)	0.0173 (11)	−0.0069 (12)
C8	0.0774 (19)	0.0721 (17)	0.112 (2)	−0.0235 (14)	0.0285 (16)	−0.0015 (15)
C9	0.0792 (17)	0.0802 (17)	0.0525 (13)	−0.0055 (13)	−0.0011 (11)	0.0135 (12)

Geometric parameters (Å, º)

N1—C1	1.333 (3)	C4—C5	1.529 (3)
N1—C9	1.452 (3)	C5—C6	1.514 (3)
N1—C4	1.461 (2)	C5—H5	0.9800
O1—C1	1.225 (2)	C6—H6A	0.9600
O2—C4	1.416 (2)	C6—H6B	0.9600
O2—C7	1.429 (3)	C6—H6C	0.9600
O3—C5	1.417 (3)	C7—C8	1.481 (3)
O3—H3	0.91 (4)	C7—H7A	0.9700
C1—C2	1.488 (3)	C7—H7B	0.9700
C2—C3	1.496 (3)	C8—H8A	0.9600
C2—H2A	0.9700	C8—H8B	0.9600
C2—H2B	0.9700	C8—H8C	0.9600
C3—C4	1.531 (3)	C9—H9A	0.9600
C3—H3A	0.9700	C9—H9B	0.9600
C3—H3B	0.9700	C9—H9C	0.9600
C1—N1—C9	122.73 (18)	C6—C5—C4	112.54 (18)
C1—N1—C4	114.92 (16)	O3—C5—H5	109.0
C9—N1—C4	122.28 (18)	C6—C5—H5	109.0
C4—O2—C7	116.73 (15)	C4—C5—H5	109.0
C5—O3—H3	112 (2)	C5—C6—H6A	109.5
O1—C1—N1	125.3 (2)	C5—C6—H6B	109.5
O1—C1—C2	125.7 (2)	H6A—C6—H6B	109.5
N1—C1—C2	109.03 (18)	C5—C6—H6C	109.5
C1—C2—C3	105.82 (18)	H6A—C6—H6C	109.5
C1—C2—H2A	110.6	H6B—C6—H6C	109.5
C3—C2—H2A	110.6	O2—C7—C8	108.10 (19)
C1—C2—H2B	110.6	O2—C7—H7A	110.1
C3—C2—H2B	110.6	C8—C7—H7A	110.1
H2A—C2—H2B	108.7	O2—C7—H7B	110.1
C2—C3—C4	107.20 (18)	C8—C7—H7B	110.1
C2—C3—H3A	110.3	H7A—C7—H7B	108.4
C4—C3—H3A	110.3	C7—C8—H8A	109.5
C2—C3—H3B	110.3	C7—C8—H8B	109.5
C4—C3—H3B	110.3	H8A—C8—H8B	109.5
H3A—C3—H3B	108.5	C7—C8—H8C	109.5
O2—C4—N1	110.49 (15)	H8A—C8—H8C	109.5
O2—C4—C5	104.17 (16)	H8B—C8—H8C	109.5
N1—C4—C5	111.34 (16)	N1—C9—H9A	109.5
O2—C4—C3	115.23 (17)	N1—C9—H9B	109.5
N1—C4—C3	102.88 (16)	H9A—C9—H9B	109.5
C5—C4—C3	112.94 (17)	N1—C9—H9C	109.5
O3—C5—C6	106.96 (18)	H9A—C9—H9C	109.5
O3—C5—C4	110.36 (17)	H9B—C9—H9C	109.5
C9—N1—C1—O1	−5.7 (3)	C9—N1—C4—C5	62.7 (2)
C4—N1—C1—O1	177.35 (19)	C1—N1—C4—C3	0.9 (2)
C9—N1—C1—C2	173.87 (19)	C9—N1—C4—C3	−176.07 (18)
C4—N1—C1—C2	−3.0 (2)	C2—C3—C4—O2	−118.65 (19)
O1—C1—C2—C3	−176.5 (2)	C2—C3—C4—N1	1.6 (2)
N1—C1—C2—C3	3.9 (2)	C2—C3—C4—C5	121.8 (2)
C1—C2—C3—C4	−3.3 (2)	O2—C4—C5—O3	176.80 (16)
C7—O2—C4—N1	−60.5 (2)	N1—C4—C5—O3	57.7 (2)
C7—O2—C4—C5	179.87 (17)	C3—C4—C5—O3	−57.4 (2)
C7—O2—C4—C3	55.6 (2)	O2—C4—C5—C6	−63.8 (2)
C1—N1—C4—O2	124.37 (18)	N1—C4—C5—C6	177.12 (18)
C9—N1—C4—O2	−52.6 (2)	C3—C4—C5—C6	62.0 (2)
C1—N1—C4—C5	−120.38 (19)	C4—O2—C7—C8	172.68 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.91 (4)	1.83 (4)	2.732 (3)	174 (3)

Symmetry code: (i) −x, −y+1, −z+1.