1-(Carbamoylmeth­yl)-5-oxopyrrolidin-3-yl acetate

The title compound, C₈H₁₂N₂O₄, was prepared from 2-(4-hydr­oxy-2-oxopyrrolidin-1-yl)acetamide and acetic anhydride. In the crystal structure, molecules are linked through N—H...O hydrogen bonds to form an extended network, which contributes to the stability of the structure in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.082
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.71
           From the CIF: _reflns_number_total               1157
           Count of symmetry unique reflns         1162
           Completeness (_total/calc)             99.57%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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.

1-(Carbamoylmethyl)-5-oxopyrrolidin-3-yl acetate

Crystal data

C8H12N2O4	F(000) = 1696
Mr = 200.20	Dx = 1.433 Mg m^−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 1534 reflections
a = 16.838 (9) Å	θ = 2.8–21.8°
b = 26.184 (14) Å	µ = 0.12 mm^−1
c = 8.419 (5) Å	T = 294 K
V = 3712 (3) Å^3	Block, white
Z = 16	0.56 × 0.34 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1157 independent reflections
Radiation source: fine-focus sealed tube	929 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.7°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→21
Tmin = 0.924, Tmax = 0.975	k = −19→34
5984 measured reflections	l = −10→10

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0537P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1157 reflections	Δρmax = 0.12 e Å^−3
136 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Absolute structure: Friedel Pairs merged
Primary atom site location: structure-invariant direct methods

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
O1	−0.08196 (8)	0.39630 (6)	0.1799 (2)	0.0548 (4)
O2	−0.05504 (10)	0.28254 (6)	0.4490 (2)	0.0521 (4)
O3	0.05305 (8)	0.40066 (6)	0.60059 (19)	0.0453 (4)
O4	0.09383 (10)	0.47893 (7)	0.6730 (3)	0.0682 (5)
N1	0.02518 (9)	0.35143 (6)	0.2690 (2)	0.0352 (4)
N2	−0.05271 (13)	0.22155 (8)	0.2603 (3)	0.0541 (5)
H2C	−0.0374 (17)	0.2130 (11)	0.167 (5)	0.067 (9)*
H2D	−0.0880 (19)	0.2029 (14)	0.321 (6)	0.095 (11)*
C1	−0.01983 (11)	0.39341 (7)	0.2541 (3)	0.0377 (4)
C2	0.02165 (13)	0.43620 (8)	0.3411 (3)	0.0430 (5)
H2A	−0.0155	0.4549	0.4071	0.052*
H2B	0.0461	0.4597	0.2668	0.052*
C3	0.08403 (12)	0.41003 (8)	0.4419 (3)	0.0420 (5)
H3	0.1334	0.4298	0.4454	0.050*
C4	0.09620 (11)	0.35903 (8)	0.3635 (3)	0.0421 (5)
H4A	0.1431	0.3594	0.2967	0.051*
H4B	0.1018	0.3322	0.4421	0.051*
C5	0.00571 (12)	0.30290 (7)	0.1991 (3)	0.0408 (5)
H5A	0.0541	0.2863	0.1636	0.049*
H5B	−0.0277	0.3084	0.1068	0.049*
C6	−0.03703 (11)	0.26827 (7)	0.3154 (2)	0.0361 (4)
C7	0.06030 (12)	0.43965 (10)	0.7043 (3)	0.0466 (5)
C8	0.02190 (15)	0.42761 (11)	0.8599 (3)	0.0584 (6)
H8A	0.0596	0.4324	0.9441	0.088*
H8B	0.0040	0.3928	0.8595	0.088*
H8C	−0.0226	0.4499	0.8760	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0506 (9)	0.0535 (9)	0.0602 (10)	0.0079 (7)	−0.0110 (9)	0.0081 (9)
O2	0.0710 (10)	0.0450 (9)	0.0402 (9)	0.0044 (7)	0.0167 (8)	0.0004 (7)
O3	0.0486 (8)	0.0515 (9)	0.0359 (8)	−0.0102 (6)	0.0049 (7)	−0.0033 (7)
O4	0.0751 (11)	0.0626 (11)	0.0668 (12)	−0.0191 (9)	0.0109 (10)	−0.0217 (10)
N1	0.0364 (8)	0.0312 (8)	0.0380 (9)	0.0018 (6)	−0.0007 (7)	−0.0013 (7)
N2	0.0743 (13)	0.0445 (10)	0.0436 (12)	−0.0142 (9)	−0.0019 (11)	−0.0024 (10)
C1	0.0411 (10)	0.0358 (10)	0.0362 (10)	0.0019 (8)	0.0066 (8)	0.0069 (9)
C2	0.0511 (11)	0.0309 (10)	0.0469 (12)	−0.0028 (8)	0.0131 (9)	0.0022 (9)
C3	0.0410 (9)	0.0446 (10)	0.0405 (11)	−0.0106 (9)	0.0091 (9)	−0.0025 (10)
C4	0.0349 (9)	0.0467 (11)	0.0447 (12)	0.0045 (8)	0.0003 (8)	−0.0010 (10)
C5	0.0508 (11)	0.0368 (10)	0.0348 (10)	0.0015 (8)	0.0045 (9)	−0.0035 (9)
C6	0.0389 (9)	0.0338 (9)	0.0357 (11)	0.0053 (8)	−0.0029 (8)	0.0013 (8)
C7	0.0408 (10)	0.0599 (14)	0.0390 (12)	0.0056 (10)	−0.0037 (9)	−0.0091 (11)
C8	0.0567 (13)	0.0784 (17)	0.0401 (12)	0.0113 (11)	−0.0006 (11)	−0.0057 (13)

Geometric parameters (Å, º)

O1—C1	1.221 (3)	C2—H2A	0.9700
O2—C6	1.224 (3)	C2—H2B	0.9700
O3—C7	1.349 (3)	C3—C4	1.504 (3)
O3—C3	1.455 (3)	C3—H3	0.9800
O4—C7	1.203 (3)	C4—H4A	0.9700
N1—C1	1.341 (2)	C4—H4B	0.9700
N1—C5	1.438 (2)	C5—C6	1.516 (3)
N1—C4	1.450 (3)	C5—H5A	0.9700
N2—C6	1.335 (3)	C5—H5B	0.9700
N2—H2C	0.86 (4)	C7—C8	1.494 (4)
N2—H2D	0.92 (4)	C8—H8A	0.9600
C1—C2	1.510 (3)	C8—H8B	0.9600
C2—C3	1.514 (3)	C8—H8C	0.9600
C7—O3—C3	115.75 (17)	N1—C4—H4A	110.9
C1—N1—C5	123.84 (17)	C3—C4—H4A	110.9
C1—N1—C4	113.91 (16)	N1—C4—H4B	110.9
C5—N1—C4	122.25 (15)	C3—C4—H4B	110.9
C6—N2—H2C	119.9 (19)	H4A—C4—H4B	108.9
C6—N2—H2D	115 (2)	N1—C5—C6	111.84 (17)
H2C—N2—H2D	124 (3)	N1—C5—H5A	109.2
O1—C1—N1	125.69 (19)	C6—C5—H5A	109.2
O1—C1—C2	126.76 (18)	N1—C5—H5B	109.2
N1—C1—C2	107.52 (17)	C6—C5—H5B	109.2
C1—C2—C3	104.90 (17)	H5A—C5—H5B	107.9
C1—C2—H2A	110.8	O2—C6—N2	123.4 (2)
C3—C2—H2A	110.8	O2—C6—C5	121.92 (19)
C1—C2—H2B	110.8	N2—C6—C5	114.7 (2)
C3—C2—H2B	110.8	O4—C7—O3	123.2 (2)
H2A—C2—H2B	108.8	O4—C7—C8	125.2 (2)
O3—C3—C4	107.61 (18)	O3—C7—C8	111.6 (2)
O3—C3—C2	110.02 (17)	C7—C8—H8A	109.5
C4—C3—C2	104.47 (19)	C7—C8—H8B	109.5
O3—C3—H3	111.5	H8A—C8—H8B	109.5
C4—C3—H3	111.5	C7—C8—H8C	109.5
C2—C3—H3	111.5	H8A—C8—H8C	109.5
N1—C4—C3	104.50 (16)	H8B—C8—H8C	109.5
C5—N1—C1—O1	−0.4 (3)	C1—N1—C4—C3	12.2 (2)
C4—N1—C1—O1	179.75 (19)	C5—N1—C4—C3	−167.59 (17)
C5—N1—C1—C2	−178.81 (18)	O3—C3—C4—N1	96.8 (2)
C4—N1—C1—C2	1.4 (2)	C2—C3—C4—N1	−20.1 (2)
O1—C1—C2—C3	167.3 (2)	C1—N1—C5—C6	−95.6 (2)
N1—C1—C2—C3	−14.3 (2)	C4—N1—C5—C6	84.2 (2)
C7—O3—C3—C4	161.18 (16)	N1—C5—C6—O2	3.4 (3)
C7—O3—C3—C2	−85.6 (2)	N1—C5—C6—N2	−176.38 (17)
C1—C2—C3—O3	−94.21 (19)	C3—O3—C7—O4	−3.9 (3)
C1—C2—C3—C4	21.0 (2)	C3—O3—C7—C8	176.10 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O2^i	0.86 (4)	2.41 (4)	3.189 (4)	152 (3)
N2—H2D···O1^ii	0.92 (4)	2.20 (4)	3.113 (3)	168 (4)

Symmetry codes: (i) −x, −y+1/2, z−1/2; (ii) −x−1/4, y−1/4, z+1/4.