4-Hydr-oxy-5-(4-methoxy-phen-yl)pyrrolidin-2-one.

In the title compound, C(11)H(13)NO(3), the pyrrolidin-2-one ring is in an envelope conformation with the hydroxyl and 4-methoxy-phenyl substituents mutually cis. The methoxy group is slighty twisted away from the mean plane of the attached benzene ring. The mol-ecules are arranged into screw chains along the c axis. These chains are inter-connected via inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into sheets parallel to the ac plane. The crystal structure is further stabilized by weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For details of ring conformations, see: Cremer & Pople (1975 ▶). For the biological properties of pyrrolidine alkaloids, see for example: Iida et al. (1986 ▶); Royles (1996 ▶). For the syntheses of compounds containing the tetra­mic acid ring, see for example: Chandrasekhar et al. (2006 ▶); Gurjar et al. (2006 ▶); Yoda et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H13NO3

M = 207.22

Orthorhombic,

a = 11.9862 (6) Å

b = 11.6251 (6) Å

c = 7.1539 (4) Å

V = 996.83 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.43 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.958, T max = 0.983

8681 measured reflections

1562 independent reflections

1218 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.109

S = 1.09

1562 reflections

145 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003899/sj2463sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003899/sj2463Isup2.hkl

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

C11H13NO3	F000 = 440
Mr = 207.22	Dx = 1.381 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1562 reflections
a = 11.9862 (6) Å	θ = 1.8–30.0º
b = 11.6251 (6) Å	µ = 0.10 mm−1
c = 7.1539 (4) Å	T = 100.0 (1) K
V = 996.83 (9) Å3	Block, colorless
Z = 4	0.43 × 0.20 × 0.17 mm

Bruker SMART APEX2 CCD area-detector diffractometer	1562 independent reflections
Radiation source: fine-focus sealed tube	1218 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.066
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.8º
ω scans	h = −16→13
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.958, Tmax = 0.983	l = −10→9
8681 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.0367P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1562 reflections	Δρmax = 0.22 e Å−3
145 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.69354 (13)	1.02873 (16)	1.1878 (3)	0.0282 (5)
O2	0.93282 (14)	0.80442 (16)	1.3464 (3)	0.0238 (4)
H1O2	0.977 (3)	0.742 (3)	1.345 (6)	0.045 (10)*
O3	0.87847 (13)	0.33500 (15)	0.8900 (3)	0.0239 (4)
N1	0.76602 (18)	0.86418 (18)	1.0604 (3)	0.0228 (5)
H1N1	0.704 (3)	0.838 (3)	1.009 (6)	0.043 (10)*
C1	0.7727 (2)	0.9651 (2)	1.1524 (4)	0.0223 (6)
C2	0.89395 (19)	0.9844 (2)	1.2029 (5)	0.0243 (6)
H2A	0.9012	1.0105	1.3311	0.029*
H2B	0.9279	1.0408	1.1206	0.029*
C3	0.94736 (19)	0.8665 (2)	1.1771 (4)	0.0222 (6)
H3A	1.0262	0.8725	1.1423	0.027*
C4	0.8761 (2)	0.8158 (2)	1.0169 (4)	0.0207 (6)
H4A	0.9018	0.8495	0.8989	0.025*
C5	0.8762 (2)	0.6876 (2)	0.9962 (4)	0.0199 (6)
C6	0.79693 (19)	0.6171 (2)	1.0788 (4)	0.0221 (6)
H6A	0.7435	0.6497	1.1568	0.027*
C7	0.79523 (19)	0.4993 (2)	1.0483 (4)	0.0229 (6)
H7A	0.7403	0.4538	1.1030	0.028*
C8	0.8756 (2)	0.4503 (2)	0.9363 (4)	0.0214 (6)
C9	0.95804 (18)	0.5175 (2)	0.8550 (4)	0.0226 (6)
H9A	1.0130	0.4839	0.7812	0.027*
C10	0.95734 (19)	0.6345 (2)	0.8850 (4)	0.0220 (6)
H10A	1.0124	0.6796	0.8298	0.026*
C11	0.7980 (2)	0.2604 (2)	0.9764 (5)	0.0287 (7)
H11A	0.8057	0.1841	0.9266	0.043*
H11B	0.7242	0.2885	0.9512	0.043*
H11C	0.8103	0.2588	1.1089	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0208 (9)	0.0270 (10)	0.0367 (12)	0.0068 (8)	−0.0016 (9)	−0.0014 (9)
O2	0.0184 (8)	0.0253 (10)	0.0276 (11)	0.0048 (8)	−0.0014 (8)	0.0003 (9)
O3	0.0211 (8)	0.0217 (9)	0.0288 (11)	0.0006 (7)	0.0017 (8)	−0.0027 (8)
N1	0.0133 (10)	0.0230 (11)	0.0321 (14)	0.0000 (9)	−0.0023 (10)	−0.0027 (10)
C1	0.0202 (12)	0.0228 (12)	0.0238 (16)	0.0016 (10)	−0.0008 (10)	0.0026 (12)
C2	0.0194 (12)	0.0219 (13)	0.0317 (16)	−0.0007 (10)	−0.0029 (11)	−0.0019 (12)
C3	0.0137 (11)	0.0240 (13)	0.0289 (14)	0.0009 (10)	0.0009 (11)	−0.0020 (12)
C4	0.0179 (12)	0.0200 (13)	0.0242 (14)	0.0006 (10)	−0.0001 (10)	−0.0017 (11)
C5	0.0137 (11)	0.0218 (13)	0.0243 (15)	0.0006 (10)	0.0000 (10)	0.0009 (11)
C6	0.0170 (11)	0.0255 (13)	0.0239 (14)	0.0016 (9)	0.0024 (11)	−0.0013 (12)
C7	0.0167 (12)	0.0243 (13)	0.0278 (15)	−0.0008 (10)	0.0027 (11)	0.0001 (12)
C8	0.0178 (12)	0.0212 (13)	0.0251 (15)	0.0021 (10)	−0.0030 (10)	−0.0015 (11)
C9	0.0173 (12)	0.0254 (13)	0.0252 (14)	0.0029 (9)	0.0040 (11)	−0.0021 (12)
C10	0.0170 (12)	0.0239 (13)	0.0251 (14)	−0.0011 (9)	0.0024 (11)	0.0013 (13)
C11	0.0250 (13)	0.0263 (15)	0.0346 (18)	−0.0003 (11)	0.0035 (12)	0.0030 (14)

O1—C1	1.229 (3)	C4—H4A	0.9800
O2—C3	1.420 (3)	C5—C6	1.387 (4)
O2—H1O2	0.90 (3)	C5—C10	1.399 (4)
O3—C8	1.381 (3)	C6—C7	1.387 (4)
O3—C11	1.437 (3)	C6—H6A	0.9300
N1—C1	1.347 (3)	C7—C8	1.376 (4)
N1—C4	1.468 (3)	C7—H7A	0.9300
N1—H1N1	0.88 (4)	C8—C9	1.387 (3)
C1—C2	1.515 (3)	C9—C10	1.378 (4)
C2—C3	1.524 (4)	C9—H9A	0.9300
C2—H2A	0.9700	C10—H10A	0.9300
C2—H2B	0.9700	C11—H11A	0.9600
C3—C4	1.547 (4)	C11—H11B	0.9600
C3—H3A	0.9800	C11—H11C	0.9600
C4—C5	1.498 (3)
C3—O2—H1O2	109 (3)	C3—C4—H4A	108.2
C8—O3—C11	117.8 (2)	C6—C5—C10	117.2 (2)
C1—N1—C4	112.6 (2)	C6—C5—C4	123.0 (2)
C1—N1—H1N1	123 (2)	C10—C5—C4	119.7 (2)
C4—N1—H1N1	123 (2)	C7—C6—C5	121.8 (2)
O1—C1—N1	125.4 (2)	C7—C6—H6A	119.1
O1—C1—C2	127.0 (2)	C5—C6—H6A	119.1
N1—C1—C2	107.6 (2)	C8—C7—C6	119.3 (2)
C1—C2—C3	103.9 (2)	C8—C7—H7A	120.3
C1—C2—H2A	111.0	C6—C7—H7A	120.3
C3—C2—H2A	111.0	C7—C8—O3	124.0 (2)
C1—C2—H2B	111.0	C7—C8—C9	120.7 (2)
C3—C2—H2B	111.0	O3—C8—C9	115.3 (2)
H2A—C2—H2B	109.0	C10—C9—C8	119.1 (2)
O2—C3—C2	107.6 (2)	C10—C9—H9A	120.5
O2—C3—C4	111.8 (2)	C8—C9—H9A	120.5
C2—C3—C4	101.6 (2)	C9—C10—C5	121.9 (2)
O2—C3—H3A	111.8	C9—C10—H10A	119.1
C2—C3—H3A	111.8	C5—C10—H10A	119.1
C4—C3—H3A	111.8	O3—C11—H11A	109.5
N1—C4—C5	113.8 (2)	O3—C11—H11B	109.5
N1—C4—C3	101.1 (2)	H11A—C11—H11B	109.5
C5—C4—C3	116.9 (2)	O3—C11—H11C	109.5
N1—C4—H4A	108.2	H11A—C11—H11C	109.5
C5—C4—H4A	108.2	H11B—C11—H11C	109.5
C4—N1—C1—O1	172.0 (3)	N1—C4—C5—C10	154.0 (2)
C4—N1—C1—C2	−8.0 (3)	C3—C4—C5—C10	−88.6 (3)
O1—C1—C2—C3	164.1 (3)	C10—C5—C6—C7	−2.1 (4)
N1—C1—C2—C3	−15.8 (3)	C4—C5—C6—C7	176.1 (3)
C1—C2—C3—O2	−86.1 (3)	C5—C6—C7—C8	1.4 (4)
C1—C2—C3—C4	31.4 (3)	C6—C7—C8—O3	−176.9 (2)
C1—N1—C4—C5	154.0 (2)	C6—C7—C8—C9	0.3 (4)
C1—N1—C4—C3	27.9 (3)	C11—O3—C8—C7	−5.2 (4)
O2—C3—C4—N1	79.4 (2)	C11—O3—C8—C9	177.4 (2)
C2—C3—C4—N1	−35.1 (2)	C7—C8—C9—C10	−1.2 (4)
O2—C3—C4—C5	−44.7 (3)	O3—C8—C9—C10	176.3 (2)
C2—C3—C4—C5	−159.2 (2)	C8—C9—C10—C5	0.4 (4)
N1—C4—C5—C6	−24.2 (4)	C6—C5—C10—C9	1.2 (4)
C3—C4—C5—C6	93.2 (3)	C4—C5—C10—C9	−177.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2—H1O2···O3ii	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3—H3A···O1iii	0.98	2.33	3.193 (3)	146
C11—H11A···O1iv	0.96	2.49	3.395 (3)	158
C6—H6A···Cg1v	0.93	2.81	3.514 (3)	133
C9—H9A···Cg1vi	0.93	2.68	3.554 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.88 (4)	2.05 (4)	2.917 (3)	167 (4)
O2—H1O2⋯O3ii	0.90 (4)	1.98 (4)	2.800 (2)	152 (3)
C3—H3A⋯O1iii	0.98	2.33	3.193 (3)	146
C11—H11A⋯O1iv	0.96	2.49	3.395 (3)	158
C6—H6A⋯Cg1v	0.93	2.81	3.514 (3)	133
C9—H9A⋯Cg1vi	0.93	2.68	3.554 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .