tert-Butyl 5-(4-methoxy-phen-yl)-1-methyl-2-oxopyrrolidin-3-yl carbonate.

In the title compound, C(17)H(23)NO(5), the pyrrolidinone ring is in an envelope conformation. The tert-butyl carbonate and 4-methoxy-phenyl groups are arranged on the same side of the pyrrolidinone ring. The meth-oxy group is coplanar with the attached benzene ring. The mol-ecules are linked into chains along the b axis via C-H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the biological properties of pyrrolidine alkaloids, see: Iida et al. (1986 ▶); Matkhalikova et al. (1969 ▶); Reddy & Rao (2006 ▶); Royles (1996 ▶). For syntheses of compounds containing a tetra­mic acid ring, see: Chandrasekhar et al. (2005 ▶, 2006 ▶); Gurjar et al. (2006 ▶); Yoda et al. (1996 ▶). For a related structure, see: Mohammat et al. (2008 ▶).

Experimental

Crystal data

C17H23NO5

M = 321.36

Monoclinic,

a = 23.9157 (4) Å

b = 6.2788 (1) Å

c = 24.1224 (4) Å

β = 101.971 (1)°

V = 3543.49 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.49 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.958, T max = 0.986

21759 measured reflections

5155 independent reflections

3632 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.125

S = 1.09

5155 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.27 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/S1600536808005527/ci2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005527/ci2562Isup2.hkl

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

C17H23NO5	F000 = 1376
Mr = 321.36	Dx = 1.205 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5155 reflections
a = 23.9157 (4) Å	θ = 1.7–30.0º
b = 6.2788 (1) Å	µ = 0.09 mm−1
c = 24.1224 (4) Å	T = 100.0 (1) K
β = 101.971 (1)º	Block, colourless
V = 3543.49 (10) Å3	0.49 × 0.18 × 0.16 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	5155 independent reflections
Radiation source: fine-focus sealed tube	3632 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.7º
ω scans	h = −33→33
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.958, Tmax = 0.986	l = −33→33
21759 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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.7489P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
5155 reflections	Δρmax = 0.30 e Å−3
213 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.74746 (4)	1.13213 (14)	0.78815 (4)	0.0273 (2)
O2	0.62826 (4)	1.08149 (14)	0.74372 (3)	0.0269 (2)
O3	0.58372 (4)	0.94891 (18)	0.65973 (4)	0.0389 (3)
O4	0.55809 (4)	1.25800 (16)	0.69566 (4)	0.0339 (2)
O5	0.63462 (4)	0.40108 (16)	1.02990 (4)	0.0344 (2)
N1	0.73427 (4)	0.81417 (16)	0.83037 (4)	0.0214 (2)
C1	0.72075 (5)	0.9674 (2)	0.79119 (5)	0.0210 (2)
C2	0.66622 (5)	0.90078 (19)	0.75060 (5)	0.0215 (2)
H2	0.6747	0.8586	0.7132	0.026*
C3	0.64411 (5)	0.7111 (2)	0.77840 (5)	0.0264 (3)
H3A	0.6300	0.5991	0.7501	0.032*
H3B	0.6125	0.7541	0.7968	0.032*
C4	0.69576 (5)	0.6296 (2)	0.82289 (5)	0.0212 (2)
H4	0.7142	0.5077	0.8068	0.025*
C5	0.68121 (5)	0.56408 (19)	0.87850 (5)	0.0207 (2)
C6	0.69206 (5)	0.3607 (2)	0.89980 (5)	0.0237 (3)
H6	0.7095	0.2605	0.8792	0.028*
C7	0.67799 (5)	0.2985 (2)	0.95081 (5)	0.0261 (3)
H7	0.6861	0.1583	0.9649	0.031*
C8	0.65208 (5)	0.4434 (2)	0.98043 (5)	0.0260 (3)
C9	0.64158 (6)	0.6501 (2)	0.96005 (5)	0.0301 (3)
H9	0.6243	0.7505	0.9807	0.036*
C10	0.65630 (5)	0.7092 (2)	0.90992 (5)	0.0273 (3)
H10	0.6494	0.8510	0.8965	0.033*
C11	0.78953 (5)	0.8054 (2)	0.86899 (6)	0.0310 (3)
H11A	0.8114	0.9339	0.8644	0.046*
H11B	0.8105	0.6795	0.8605	0.046*
H11C	0.7840	0.7970	0.9081	0.046*
C12	0.58881 (5)	1.0836 (2)	0.69533 (5)	0.0235 (3)
C13	0.50992 (5)	1.3048 (2)	0.64753 (6)	0.0335 (3)
C14	0.48639 (8)	1.5091 (3)	0.66671 (10)	0.0726 (7)
H14A	0.4732	1.4835	0.7020	0.109*
H14B	0.4543	1.5585	0.6374	0.109*
H14C	0.5164	1.6179	0.6732	0.109*
C15	0.53223 (8)	1.3349 (4)	0.59443 (9)	0.0818 (8)
H15A	0.5462	1.1985	0.5830	0.123*
H15B	0.5636	1.4383	0.6014	0.123*
H15C	0.5015	1.3878	0.5642	0.123*
C16	0.46593 (6)	1.1316 (3)	0.64296 (8)	0.0547 (5)
H16A	0.4571	1.1058	0.6803	0.082*
H16B	0.4808	1.0008	0.6293	0.082*
H16C	0.4311	1.1753	0.6163	0.082*
C17	0.64211 (8)	0.1904 (3)	1.05145 (7)	0.0444 (4)
H17A	0.6283	0.1816	1.0869	0.067*
H17B	0.6828	0.1530	1.0586	0.067*
H17C	0.6204	0.0913	1.0237	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (5)	0.0219 (5)	0.0342 (5)	−0.0031 (4)	0.0121 (4)	0.0018 (4)
O2	0.0266 (4)	0.0269 (5)	0.0260 (4)	0.0102 (4)	0.0026 (3)	−0.0026 (4)
O3	0.0367 (5)	0.0479 (7)	0.0282 (5)	0.0156 (5)	−0.0021 (4)	−0.0096 (5)
O4	0.0270 (5)	0.0296 (5)	0.0414 (5)	0.0104 (4)	−0.0019 (4)	−0.0008 (4)
O5	0.0511 (6)	0.0321 (6)	0.0239 (4)	−0.0066 (5)	0.0167 (4)	−0.0021 (4)
N1	0.0198 (5)	0.0218 (5)	0.0217 (5)	−0.0030 (4)	0.0023 (4)	0.0007 (4)
C1	0.0222 (5)	0.0204 (6)	0.0224 (6)	0.0020 (5)	0.0098 (4)	−0.0017 (5)
C2	0.0228 (6)	0.0201 (6)	0.0216 (5)	0.0064 (5)	0.0046 (4)	−0.0001 (5)
C3	0.0241 (6)	0.0279 (7)	0.0248 (6)	−0.0042 (5)	−0.0002 (5)	0.0015 (5)
C4	0.0234 (6)	0.0180 (6)	0.0222 (6)	−0.0025 (5)	0.0050 (4)	−0.0011 (5)
C5	0.0202 (5)	0.0207 (6)	0.0210 (5)	−0.0027 (5)	0.0037 (4)	−0.0009 (5)
C6	0.0260 (6)	0.0212 (6)	0.0250 (6)	0.0007 (5)	0.0075 (5)	−0.0001 (5)
C7	0.0316 (6)	0.0206 (6)	0.0262 (6)	−0.0006 (5)	0.0064 (5)	0.0019 (5)
C8	0.0294 (6)	0.0281 (7)	0.0209 (6)	−0.0071 (5)	0.0060 (5)	−0.0031 (5)
C9	0.0389 (7)	0.0252 (7)	0.0287 (6)	−0.0007 (6)	0.0128 (5)	−0.0065 (6)
C10	0.0347 (7)	0.0208 (6)	0.0272 (6)	0.0004 (5)	0.0083 (5)	−0.0003 (5)
C11	0.0228 (6)	0.0358 (8)	0.0312 (7)	−0.0027 (6)	−0.0014 (5)	0.0025 (6)
C12	0.0206 (5)	0.0274 (7)	0.0240 (6)	0.0037 (5)	0.0083 (5)	0.0038 (5)
C13	0.0204 (6)	0.0369 (8)	0.0409 (8)	0.0074 (6)	0.0011 (5)	0.0119 (6)
C14	0.0545 (11)	0.0502 (12)	0.0977 (16)	0.0303 (10)	−0.0199 (11)	−0.0041 (11)
C15	0.0520 (10)	0.134 (2)	0.0651 (12)	0.0401 (13)	0.0254 (9)	0.0665 (14)
C16	0.0263 (7)	0.0538 (11)	0.0761 (12)	−0.0002 (7)	−0.0078 (7)	0.0168 (10)
C17	0.0646 (10)	0.0396 (9)	0.0351 (8)	−0.0043 (8)	0.0242 (7)	0.0091 (7)

O1—C1	1.2257 (15)	C7—H7	0.95
O2—C12	1.3403 (14)	C8—C9	1.3917 (19)
O2—C2	1.4411 (14)	C9—C10	1.3788 (18)
O3—C12	1.1934 (15)	C9—H9	0.95
O4—C12	1.3195 (15)	C10—H10	0.95
O4—C13	1.4854 (15)	C11—H11A	0.98
O5—C8	1.3694 (15)	C11—H11B	0.98
O5—C17	1.4188 (18)	C11—H11C	0.98
N1—C1	1.3404 (15)	C13—C15	1.498 (2)
N1—C11	1.4516 (15)	C13—C16	1.501 (2)
N1—C4	1.4679 (15)	C13—C14	1.512 (2)
C1—C2	1.5182 (16)	C14—H14A	0.98
C2—C3	1.5150 (18)	C14—H14B	0.98
C2—H2	1.00	C14—H14C	0.98
C3—C4	1.5459 (16)	C15—H15A	0.98
C3—H3A	0.99	C15—H15B	0.98
C3—H3B	0.99	C15—H15C	0.98
C4—C5	1.5112 (16)	C16—H16A	0.98
C4—H4	1.00	C16—H16B	0.98
C5—C6	1.3807 (17)	C16—H16C	0.98
C5—C10	1.3951 (17)	C17—H17A	0.98
C6—C7	1.3970 (17)	C17—H17B	0.98
C6—H6	0.95	C17—H17C	0.98
C7—C8	1.3807 (18)
C12—O2—C2	114.90 (9)	C9—C10—C5	121.08 (12)
C12—O4—C13	120.12 (11)	C9—C10—H10	119.5
C8—O5—C17	117.54 (11)	C5—C10—H10	119.5
C1—N1—C11	122.27 (10)	N1—C11—H11A	109.5
C1—N1—C4	115.26 (9)	N1—C11—H11B	109.5
C11—N1—C4	120.90 (10)	H11A—C11—H11B	109.5
O1—C1—N1	126.54 (11)	N1—C11—H11C	109.5
O1—C1—C2	125.62 (11)	H11A—C11—H11C	109.5
N1—C1—C2	107.83 (10)	H11B—C11—H11C	109.5
O2—C2—C3	113.61 (10)	O3—C12—O4	128.22 (11)
O2—C2—C1	107.08 (9)	O3—C12—O2	124.61 (11)
C3—C2—C1	105.26 (9)	O4—C12—O2	107.17 (10)
O2—C2—H2	110.2	O4—C13—C15	109.70 (11)
C3—C2—H2	110.2	O4—C13—C16	109.42 (12)
C1—C2—H2	110.2	C15—C13—C16	113.41 (17)
C2—C3—C4	105.40 (9)	O4—C13—C14	101.90 (12)
C2—C3—H3A	110.7	C15—C13—C14	112.05 (16)
C4—C3—H3A	110.7	C16—C13—C14	109.72 (14)
C2—C3—H3B	110.7	C13—C14—H14A	109.5
C4—C3—H3B	110.7	C13—C14—H14B	109.5
H3A—C3—H3B	108.8	H14A—C14—H14B	109.5
N1—C4—C5	111.08 (9)	C13—C14—H14C	109.5
N1—C4—C3	102.39 (10)	H14A—C14—H14C	109.5
C5—C4—C3	114.10 (10)	H14B—C14—H14C	109.5
N1—C4—H4	109.7	C13—C15—H15A	109.5
C5—C4—H4	109.7	C13—C15—H15B	109.5
C3—C4—H4	109.7	H15A—C15—H15B	109.5
C6—C5—C10	118.05 (11)	C13—C15—H15C	109.5
C6—C5—C4	121.46 (11)	H15A—C15—H15C	109.5
C10—C5—C4	120.49 (11)	H15B—C15—H15C	109.5
C5—C6—C7	121.68 (12)	C13—C16—H16A	109.5
C5—C6—H6	119.2	C13—C16—H16B	109.5
C7—C6—H6	119.2	H16A—C16—H16B	109.5
C8—C7—C6	119.19 (12)	C13—C16—H16C	109.5
C8—C7—H7	120.4	H16A—C16—H16C	109.5
C6—C7—H7	120.4	H16B—C16—H16C	109.5
O5—C8—C7	125.01 (12)	O5—C17—H17A	109.5
O5—C8—C9	115.06 (12)	O5—C17—H17B	109.5
C7—C8—C9	119.93 (12)	H17A—C17—H17B	109.5
C10—C9—C8	120.04 (12)	O5—C17—H17C	109.5
C10—C9—H9	120.0	H17A—C17—H17C	109.5
C8—C9—H9	120.0	H17B—C17—H17C	109.5
C11—N1—C1—O1	−12.17 (19)	C3—C4—C5—C10	−58.06 (15)
C4—N1—C1—O1	−177.97 (11)	C10—C5—C6—C7	0.94 (18)
C11—N1—C1—C2	167.57 (11)	C4—C5—C6—C7	−179.13 (11)
C4—N1—C1—C2	1.77 (13)	C5—C6—C7—C8	0.63 (18)
C12—O2—C2—C3	−88.44 (12)	C17—O5—C8—C7	−2.06 (19)
C12—O2—C2—C1	155.79 (10)	C17—O5—C8—C9	177.48 (13)
O1—C1—C2—O2	−48.13 (15)	C6—C7—C8—O5	177.96 (11)
N1—C1—C2—O2	132.13 (10)	C6—C7—C8—C9	−1.56 (19)
O1—C1—C2—C3	−169.34 (11)	O5—C8—C9—C10	−178.65 (12)
N1—C1—C2—C3	10.92 (12)	C7—C8—C9—C10	0.9 (2)
O2—C2—C3—C4	−135.30 (10)	C8—C9—C10—C5	0.7 (2)
C1—C2—C3—C4	−18.46 (12)	C6—C5—C10—C9	−1.61 (18)
C1—N1—C4—C5	−135.47 (11)	C4—C5—C10—C9	178.45 (11)
C11—N1—C4—C5	58.52 (14)	C13—O4—C12—O3	0.5 (2)
C1—N1—C4—C3	−13.27 (13)	C13—O4—C12—O2	−179.21 (10)
C11—N1—C4—C3	−179.29 (11)	C2—O2—C12—O3	0.52 (18)
C2—C3—C4—N1	18.89 (12)	C2—O2—C12—O4	−179.77 (9)
C2—C3—C4—C5	139.01 (11)	C12—O4—C13—C15	−63.23 (18)
N1—C4—C5—C6	−122.88 (12)	C12—O4—C13—C16	61.79 (16)
C3—C4—C5—C6	122.01 (12)	C12—O4—C13—C14	177.89 (14)
N1—C4—C5—C10	57.05 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	1.00	2.35	2.9633 (15)	119
C4—H4···O1ii	1.00	2.56	3.5238 (15)	162
C11—H11A···O1	0.98	2.47	2.8652 (16)	104
C15—H15A···O3	0.98	2.45	3.011 (3)	116
C16—H16B···O3	0.98	2.44	2.9904 (19)	115
C17—H17A···O3iii	0.98	2.38	3.324 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	1.00	2.35	2.9633 (15)	119
C4—H4⋯O1ii	1.00	2.56	3.5238 (15)	162
C11—H11A⋯O1	0.98	2.47	2.8652 (16)	104
C15—H15A⋯O3	0.98	2.45	3.011 (3)	116
C16—H16B⋯O3	0.98	2.44	2.9904 (19)	115
C17—H17A⋯O3iii	0.98	2.38	3.324 (2)	161

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