3,3-Dimethyl­pyrrolidine-2,4-dione

In the title compound, C₆H₉NO₂, the asymmetric unit consists of three mol­ecules. All the five-membered rings are essentially planar. The mol­ecule is stabilized by inter­molecular N—H...O and C—H...O inter­actions, forming a two-dimensional network parallel to (100).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    -   C16     ..       5.19 su

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3,3-Dimethylpyrrolidine-2,4-dione

Crystal data

C6H9NO2	F(000) = 1632
Mr = 127.14	Dx = 1.229 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4272 reflections
a = 28.745 (6) Å	θ = 1.4–26.0°
b = 12.653 (2) Å	µ = 0.09 mm^−1
c = 11.588 (2) Å	T = 293 K
β = 101.966 (3)°	Block, colorless
V = 4122.9 (14) Å^3	0.44 × 0.36 × 0.26 mm
Z = 24

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4053 independent reflections
Radiation source: fine-focus sealed tube	3168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 1.4°
ω scans	h = −35→32
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −13→15
Tmin = 0.960, Tmax = 0.976	l = −14→14
10969 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0623P)^2 + 0.9776P] where P = (Fo^2 + 2Fc^2)/3
4053 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−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
O1	0.21539 (4)	0.14880 (10)	0.06303 (13)	0.0727 (4)
O2	0.33034 (5)	−0.11670 (9)	0.07031 (13)	0.0715 (4)
O3	0.35883 (5)	0.51059 (9)	0.28424 (12)	0.0721 (4)
O4	0.44104 (5)	0.80054 (9)	0.48385 (12)	0.0721 (4)
O5	0.42845 (5)	0.28958 (10)	0.56501 (12)	0.0793 (4)
O6	0.39132 (5)	0.01377 (9)	0.29263 (10)	0.0629 (4)
N1	0.29011 (5)	0.14130 (10)	0.02638 (12)	0.0525 (3)
H1A	0.2913	0.2063	0.0055	0.063*
N2	0.38185 (5)	0.77945 (10)	0.32147 (12)	0.0501 (3)
H2C	0.3775	0.8456	0.3059	0.060*
N3	0.43450 (5)	0.02780 (10)	0.48007 (11)	0.0503 (3)
H3A	0.4409	−0.0384	0.4899	0.060*
C1	0.25225 (6)	0.10054 (12)	0.05919 (15)	0.0492 (4)
C2	0.32908 (6)	0.06878 (12)	0.02820 (15)	0.0499 (4)
H2A	0.3572	0.0906	0.0850	0.060*
H2B	0.3369	0.0630	−0.0490	0.060*
C3	0.30963 (6)	−0.03359 (12)	0.06416 (14)	0.0486 (4)
C4	0.26077 (6)	−0.01503 (12)	0.09032 (14)	0.0465 (4)
C5	0.26230 (7)	−0.03284 (17)	0.22185 (16)	0.0712 (5)
H5A	0.2853	0.0137	0.2676	0.107*
H5B	0.2710	−0.1048	0.2420	0.107*
H5C	0.2315	−0.0186	0.2384	0.107*
C6	0.22311 (7)	−0.08410 (14)	0.01425 (19)	0.0678 (5)
H6A	0.1926	−0.0685	0.0314	0.102*
H6B	0.2306	−0.1572	0.0309	0.102*
H6C	0.2224	−0.0702	−0.0675	0.102*
C7	0.41462 (6)	0.74450 (12)	0.41232 (14)	0.0491 (4)
C8	0.35414 (6)	0.69772 (12)	0.25084 (14)	0.0512 (4)
H8A	0.3587	0.6992	0.1703	0.061*
H8B	0.3205	0.7055	0.2504	0.061*
C9	0.37364 (6)	0.59770 (12)	0.31230 (14)	0.0489 (4)
C10	0.41504 (6)	0.62458 (12)	0.41241 (15)	0.0503 (4)
C11	0.46072 (7)	0.58680 (15)	0.3767 (2)	0.0784 (6)
H11A	0.4624	0.6161	0.3013	0.118*
H11B	0.4606	0.5110	0.3719	0.118*
H11C	0.4878	0.6096	0.4346	0.118*
C12	0.40941 (9)	0.57856 (15)	0.52987 (18)	0.0759 (6)
H12A	0.4356	0.6008	0.5907	0.114*
H12B	0.4090	0.5028	0.5251	0.114*
H12C	0.3801	0.6030	0.5480	0.114*
C13	0.41040 (5)	0.06705 (11)	0.37850 (14)	0.0454 (4)
C14	0.44909 (6)	0.10522 (13)	0.57284 (15)	0.0553 (4)
H14A	0.4835	0.1087	0.5966	0.066*
H14B	0.4358	0.0892	0.6412	0.066*
C15	0.42895 (6)	0.20663 (13)	0.51479 (15)	0.0536 (4)
C16	0.41035 (6)	0.18679 (11)	0.38437 (14)	0.0486 (4)
C17	0.36177 (7)	0.23502 (14)	0.33749 (18)	0.0697 (5)
H17A	0.3514	0.2173	0.2556	0.105*
H17B	0.3637	0.3105	0.3460	0.105*
H17C	0.3394	0.2078	0.3812	0.105*
C18	0.44734 (7)	0.22915 (16)	0.31750 (17)	0.0715 (5)
H18A	0.4386	0.2086	0.2361	0.107*
H18B	0.4780	0.2005	0.3516	0.107*
H18C	0.4485	0.3048	0.3230	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0582 (8)	0.0490 (7)	0.1200 (11)	0.0148 (6)	0.0394 (7)	0.0199 (7)
O2	0.0765 (9)	0.0489 (7)	0.0930 (10)	0.0230 (6)	0.0269 (7)	0.0087 (6)
O3	0.0814 (9)	0.0406 (7)	0.0881 (10)	−0.0110 (6)	0.0032 (7)	−0.0076 (6)
O4	0.0791 (9)	0.0409 (6)	0.0812 (9)	−0.0033 (6)	−0.0184 (7)	−0.0026 (6)
O5	0.1108 (11)	0.0518 (8)	0.0801 (9)	−0.0172 (7)	0.0313 (8)	−0.0249 (7)
O6	0.0860 (9)	0.0411 (6)	0.0547 (7)	−0.0015 (6)	−0.0015 (6)	−0.0063 (5)
N1	0.0482 (8)	0.0382 (7)	0.0728 (9)	0.0055 (6)	0.0166 (6)	0.0091 (6)
N2	0.0580 (8)	0.0326 (6)	0.0565 (8)	0.0023 (6)	0.0045 (6)	0.0040 (6)
N3	0.0543 (8)	0.0397 (7)	0.0551 (8)	−0.0003 (6)	0.0071 (6)	−0.0021 (6)
C1	0.0486 (9)	0.0413 (8)	0.0582 (10)	0.0059 (7)	0.0120 (7)	0.0038 (7)
C2	0.0469 (9)	0.0495 (9)	0.0534 (9)	0.0076 (7)	0.0106 (7)	0.0042 (7)
C3	0.0554 (9)	0.0450 (9)	0.0443 (9)	0.0097 (7)	0.0081 (7)	0.0025 (7)
C4	0.0522 (9)	0.0399 (8)	0.0483 (9)	0.0051 (6)	0.0127 (7)	0.0052 (6)
C5	0.0773 (13)	0.0839 (14)	0.0564 (11)	0.0185 (10)	0.0231 (9)	0.0156 (10)
C6	0.0709 (12)	0.0550 (11)	0.0769 (13)	−0.0077 (9)	0.0138 (10)	−0.0018 (9)
C7	0.0513 (9)	0.0358 (8)	0.0578 (9)	0.0003 (7)	0.0061 (7)	0.0004 (7)
C8	0.0557 (10)	0.0455 (9)	0.0499 (9)	−0.0034 (7)	0.0051 (7)	0.0020 (7)
C9	0.0534 (9)	0.0392 (8)	0.0557 (9)	−0.0021 (7)	0.0150 (7)	−0.0019 (7)
C10	0.0513 (9)	0.0348 (8)	0.0616 (10)	0.0022 (6)	0.0042 (7)	0.0031 (7)
C11	0.0598 (12)	0.0565 (11)	0.1171 (18)	0.0099 (9)	0.0145 (11)	−0.0042 (11)
C12	0.1015 (16)	0.0535 (11)	0.0655 (12)	−0.0066 (10)	0.0007 (11)	0.0114 (9)
C13	0.0499 (9)	0.0376 (8)	0.0500 (9)	−0.0013 (7)	0.0133 (7)	−0.0026 (7)
C14	0.0562 (10)	0.0592 (10)	0.0500 (9)	−0.0100 (8)	0.0098 (8)	−0.0068 (8)
C15	0.0598 (10)	0.0443 (9)	0.0617 (10)	−0.0150 (7)	0.0243 (8)	−0.0105 (7)
C16	0.0591 (10)	0.0362 (8)	0.0530 (9)	−0.0066 (7)	0.0176 (7)	−0.0018 (6)
C17	0.0771 (13)	0.0465 (10)	0.0849 (13)	0.0090 (9)	0.0152 (10)	0.0028 (9)
C18	0.0844 (14)	0.0671 (12)	0.0692 (12)	−0.0189 (10)	0.0301 (10)	0.0039 (10)

Geometric parameters (Å, º)

O1—C1	1.2317 (19)	C6—H6C	0.9600
O2—C3	1.2031 (18)	C7—C10	1.517 (2)
O3—C9	1.2018 (18)	C8—C9	1.502 (2)
O4—C7	1.2270 (18)	C8—H8A	0.9700
O5—C15	1.2016 (19)	C8—H8B	0.9700
O6—C13	1.2326 (18)	C9—C10	1.518 (2)
N1—C1	1.329 (2)	C10—C12	1.520 (3)
N1—C2	1.445 (2)	C10—C11	1.533 (3)
N1—H1A	0.8600	C11—H11A	0.9600
N2—C7	1.334 (2)	C11—H11B	0.9600
N2—C8	1.4503 (19)	C11—H11C	0.9600
N2—H2C	0.8600	C12—H12A	0.9600
N3—C13	1.3318 (19)	C12—H12B	0.9600
N3—C14	1.451 (2)	C12—H12C	0.9600
N3—H3A	0.8600	C13—C16	1.517 (2)
C1—C4	1.514 (2)	C14—C15	1.508 (2)
C2—C3	1.503 (2)	C14—H14A	0.9700
C2—H2A	0.9700	C14—H14B	0.9700
C2—H2B	0.9700	C15—C16	1.516 (2)
C3—C4	1.515 (2)	C16—C17	1.517 (2)
C4—C6	1.522 (2)	C16—C18	1.536 (2)
C4—C5	1.532 (2)	C17—H17A	0.9600
C5—H5A	0.9600	C17—H17B	0.9600
C5—H5B	0.9600	C17—H17C	0.9600
C5—H5C	0.9600	C18—H18A	0.9600
C6—H6A	0.9600	C18—H18B	0.9600
C6—H6B	0.9600	C18—H18C	0.9600
C1—N1—C2	115.32 (13)	C8—C9—C10	109.26 (12)
C1—N1—H1A	122.3	C7—C10—C9	102.63 (12)
C2—N1—H1A	122.3	C7—C10—C12	112.43 (15)
C7—N2—C8	115.10 (12)	C9—C10—C12	112.74 (15)
C7—N2—H2C	122.4	C7—C10—C11	108.58 (14)
C8—N2—H2C	122.4	C9—C10—C11	107.67 (15)
C13—N3—C14	114.88 (13)	C12—C10—C11	112.24 (16)
C13—N3—H3A	122.6	C10—C11—H11A	109.5
C14—N3—H3A	122.6	C10—C11—H11B	109.5
O1—C1—N1	125.42 (15)	H11A—C11—H11B	109.5
O1—C1—C4	124.62 (15)	C10—C11—H11C	109.5
N1—C1—C4	109.96 (13)	H11A—C11—H11C	109.5
N1—C2—C3	102.68 (13)	H11B—C11—H11C	109.5
N1—C2—H2A	111.2	C10—C12—H12A	109.5
C3—C2—H2A	111.2	C10—C12—H12B	109.5
N1—C2—H2B	111.2	H12A—C12—H12B	109.5
C3—C2—H2B	111.2	C10—C12—H12C	109.5
H2A—C2—H2B	109.1	H12A—C12—H12C	109.5
O2—C3—C2	124.16 (16)	H12B—C12—H12C	109.5
O2—C3—C4	126.25 (15)	O6—C13—N3	124.92 (14)
C2—C3—C4	109.59 (12)	O6—C13—C16	125.32 (14)
C1—C4—C3	102.29 (12)	N3—C13—C16	109.76 (13)
C1—C4—C6	110.86 (13)	N3—C14—C15	102.64 (13)
C3—C4—C6	111.87 (14)	N3—C14—H14A	111.2
C1—C4—C5	110.42 (14)	C15—C14—H14A	111.2
C3—C4—C5	109.85 (13)	N3—C14—H14B	111.2
C6—C4—C5	111.21 (15)	C15—C14—H14B	111.2
C4—C5—H5A	109.5	H14A—C14—H14B	109.2
C4—C5—H5B	109.5	O5—C15—C14	124.70 (16)
H5A—C5—H5B	109.5	O5—C15—C16	126.18 (16)
C4—C5—H5C	109.5	C14—C15—C16	109.11 (13)
H5A—C5—H5C	109.5	C15—C16—C13	101.93 (13)
H5B—C5—H5C	109.5	C15—C16—C17	113.48 (14)
C4—C6—H6A	109.5	C13—C16—C17	113.27 (13)
C4—C6—H6B	109.5	C15—C16—C18	107.89 (13)
H6A—C6—H6B	109.5	C13—C16—C18	108.59 (14)
C4—C6—H6C	109.5	C17—C16—C18	111.16 (15)
H6A—C6—H6C	109.5	C16—C17—H17A	109.5
H6B—C6—H6C	109.5	C16—C17—H17B	109.5
O4—C7—N2	125.33 (14)	H17A—C17—H17B	109.5
O4—C7—C10	125.02 (14)	C16—C17—H17C	109.5
N2—C7—C10	109.64 (13)	H17A—C17—H17C	109.5
N2—C8—C9	103.05 (12)	H17B—C17—H17C	109.5
N2—C8—H8A	111.2	C16—C18—H18A	109.5
C9—C8—H8A	111.2	C16—C18—H18B	109.5
N2—C8—H8B	111.2	H18A—C18—H18B	109.5
C9—C8—H8B	111.2	C16—C18—H18C	109.5
H8A—C8—H8B	109.1	H18A—C18—H18C	109.5
O3—C9—C8	124.60 (15)	H18B—C18—H18C	109.5
O3—C9—C10	126.13 (15)
C2—N1—C1—O1	−179.55 (16)	O4—C7—C10—C11	−70.0 (2)
C2—N1—C1—C4	−0.1 (2)	N2—C7—C10—C11	108.80 (17)
C1—N1—C2—C3	2.50 (19)	O3—C9—C10—C7	−175.50 (17)
N1—C2—C3—O2	175.96 (16)	C8—C9—C10—C7	5.59 (18)
N1—C2—C3—C4	−3.87 (17)	O3—C9—C10—C12	−54.3 (2)
O1—C1—C4—C3	177.14 (16)	C8—C9—C10—C12	126.78 (16)
N1—C1—C4—C3	−2.31 (17)	O3—C9—C10—C11	70.0 (2)
O1—C1—C4—C6	57.7 (2)	C8—C9—C10—C11	−108.87 (15)
N1—C1—C4—C6	−121.72 (16)	C14—N3—C13—O6	−173.29 (16)
O1—C1—C4—C5	−66.0 (2)	C14—N3—C13—C16	7.15 (19)
N1—C1—C4—C5	114.57 (16)	C13—N3—C14—C15	1.25 (18)
O2—C3—C4—C1	−176.02 (17)	N3—C14—C15—O5	171.59 (16)
C2—C3—C4—C1	3.81 (16)	N3—C14—C15—C16	−9.12 (17)
O2—C3—C4—C6	−57.3 (2)	O5—C15—C16—C13	−168.00 (17)
C2—C3—C4—C6	122.51 (15)	C14—C15—C16—C13	12.73 (17)
O2—C3—C4—C5	66.7 (2)	O5—C15—C16—C17	−45.9 (2)
C2—C3—C4—C5	−113.47 (16)	C14—C15—C16—C17	134.87 (15)
C8—N2—C7—O4	−178.53 (17)	O5—C15—C16—C18	77.8 (2)
C8—N2—C7—C10	2.7 (2)	C14—C15—C16—C18	−101.51 (16)
C7—N2—C8—C9	1.00 (19)	O6—C13—C16—C15	168.38 (16)
N2—C8—C9—O3	176.84 (17)	N3—C13—C16—C15	−12.06 (17)
N2—C8—C9—C10	−4.24 (18)	O6—C13—C16—C17	46.1 (2)
O4—C7—C10—C9	176.17 (17)	N3—C13—C16—C17	−134.34 (15)
N2—C7—C10—C9	−5.01 (18)	O6—C13—C16—C18	−77.9 (2)
O4—C7—C10—C12	54.8 (2)	N3—C13—C16—C18	101.66 (16)
N2—C7—C10—C12	−126.40 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	1.99	2.8433 (19)	171
N2—H2C···O6^ii	0.86	2.18	3.0023 (18)	161
N3—H3A···O4^iii	0.86	2.04	2.8814 (18)	166
C2—H2A···O6	0.97	2.59	3.287 (2)	129
C5—H5C···O3^iv	0.96	2.58	3.511 (3)	163
C8—H8A···O5^v	0.97	2.56	3.337 (2)	137
C17—H17C···O2^vi	0.96	2.54	3.369 (3)	145

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+1/2, y−1/2, −z+1/2; (v) x, −y+1, z−1/2; (vi) x, −y, z+1/2.