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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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012372/is2021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012372/is2021Isup2.hkl
Contains datablock I

CCDC reference: 608422

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

Computing details top

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 top
Crystal data top
C6H9NO2F(000) = 1632
Mr = 127.14Dx = 1.229 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4272 reflections
a = 28.745 (6) Åθ = 1.4–26.0°
b = 12.653 (2) ŵ = 0.09 mm1
c = 11.588 (2) ÅT = 293 K
β = 101.966 (3)°Block, colorless
V = 4122.9 (14) Å30.44 × 0.36 × 0.26 mm
Z = 24
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4053 independent reflections
Radiation source: fine-focus sealed tube3168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 1.4°
ω scansh = 3532
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1315
Tmin = 0.960, Tmax = 0.976l = 1414
10969 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0623P)2 + 0.9776P]
where P = (Fo2 + 2Fc2)/3
4053 reflections(Δ/σ)max < 0.001
250 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.21539 (4)0.14880 (10)0.06303 (13)0.0727 (4)
O20.33034 (5)0.11670 (9)0.07031 (13)0.0715 (4)
O30.35883 (5)0.51059 (9)0.28424 (12)0.0721 (4)
O40.44104 (5)0.80054 (9)0.48385 (12)0.0721 (4)
O50.42845 (5)0.28958 (10)0.56501 (12)0.0793 (4)
O60.39132 (5)0.01377 (9)0.29263 (10)0.0629 (4)
N10.29011 (5)0.14130 (10)0.02638 (12)0.0525 (3)
H1A0.29130.20630.00550.063*
N20.38185 (5)0.77945 (10)0.32147 (12)0.0501 (3)
H2C0.37750.84560.30590.060*
N30.43450 (5)0.02780 (10)0.48007 (11)0.0503 (3)
H3A0.44090.03840.48990.060*
C10.25225 (6)0.10054 (12)0.05919 (15)0.0492 (4)
C20.32908 (6)0.06878 (12)0.02820 (15)0.0499 (4)
H2A0.35720.09060.08500.060*
H2B0.33690.06300.04900.060*
C30.30963 (6)0.03359 (12)0.06416 (14)0.0486 (4)
C40.26077 (6)0.01503 (12)0.09032 (14)0.0465 (4)
C50.26230 (7)0.03284 (17)0.22185 (16)0.0712 (5)
H5A0.28530.01370.26760.107*
H5B0.27100.10480.24200.107*
H5C0.23150.01860.23840.107*
C60.22311 (7)0.08410 (14)0.01425 (19)0.0678 (5)
H6A0.19260.06850.03140.102*
H6B0.23060.15720.03090.102*
H6C0.22240.07020.06750.102*
C70.41462 (6)0.74450 (12)0.41232 (14)0.0491 (4)
C80.35414 (6)0.69772 (12)0.25084 (14)0.0512 (4)
H8A0.35870.69920.17030.061*
H8B0.32050.70550.25040.061*
C90.37364 (6)0.59770 (12)0.31230 (14)0.0489 (4)
C100.41504 (6)0.62458 (12)0.41241 (15)0.0503 (4)
C110.46072 (7)0.58680 (15)0.3767 (2)0.0784 (6)
H11A0.46240.61610.30130.118*
H11B0.46060.51100.37190.118*
H11C0.48780.60960.43460.118*
C120.40941 (9)0.57856 (15)0.52987 (18)0.0759 (6)
H12A0.43560.60080.59070.114*
H12B0.40900.50280.52510.114*
H12C0.38010.60300.54800.114*
C130.41040 (5)0.06705 (11)0.37850 (14)0.0454 (4)
C140.44909 (6)0.10522 (13)0.57284 (15)0.0553 (4)
H14A0.48350.10870.59660.066*
H14B0.43580.08920.64120.066*
C150.42895 (6)0.20663 (13)0.51479 (15)0.0536 (4)
C160.41035 (6)0.18679 (11)0.38437 (14)0.0486 (4)
C170.36177 (7)0.23502 (14)0.33749 (18)0.0697 (5)
H17A0.35140.21730.25560.105*
H17B0.36370.31050.34600.105*
H17C0.33940.20780.38120.105*
C180.44734 (7)0.22915 (16)0.31750 (17)0.0715 (5)
H18A0.43860.20860.23610.107*
H18B0.47800.20050.35160.107*
H18C0.44850.30480.32300.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0582 (8)0.0490 (7)0.1200 (11)0.0148 (6)0.0394 (7)0.0199 (7)
O20.0765 (9)0.0489 (7)0.0930 (10)0.0230 (6)0.0269 (7)0.0087 (6)
O30.0814 (9)0.0406 (7)0.0881 (10)0.0110 (6)0.0032 (7)0.0076 (6)
O40.0791 (9)0.0409 (6)0.0812 (9)0.0033 (6)0.0184 (7)0.0026 (6)
O50.1108 (11)0.0518 (8)0.0801 (9)0.0172 (7)0.0313 (8)0.0249 (7)
O60.0860 (9)0.0411 (6)0.0547 (7)0.0015 (6)0.0015 (6)0.0063 (5)
N10.0482 (8)0.0382 (7)0.0728 (9)0.0055 (6)0.0166 (6)0.0091 (6)
N20.0580 (8)0.0326 (6)0.0565 (8)0.0023 (6)0.0045 (6)0.0040 (6)
N30.0543 (8)0.0397 (7)0.0551 (8)0.0003 (6)0.0071 (6)0.0021 (6)
C10.0486 (9)0.0413 (8)0.0582 (10)0.0059 (7)0.0120 (7)0.0038 (7)
C20.0469 (9)0.0495 (9)0.0534 (9)0.0076 (7)0.0106 (7)0.0042 (7)
C30.0554 (9)0.0450 (9)0.0443 (9)0.0097 (7)0.0081 (7)0.0025 (7)
C40.0522 (9)0.0399 (8)0.0483 (9)0.0051 (6)0.0127 (7)0.0052 (6)
C50.0773 (13)0.0839 (14)0.0564 (11)0.0185 (10)0.0231 (9)0.0156 (10)
C60.0709 (12)0.0550 (11)0.0769 (13)0.0077 (9)0.0138 (10)0.0018 (9)
C70.0513 (9)0.0358 (8)0.0578 (9)0.0003 (7)0.0061 (7)0.0004 (7)
C80.0557 (10)0.0455 (9)0.0499 (9)0.0034 (7)0.0051 (7)0.0020 (7)
C90.0534 (9)0.0392 (8)0.0557 (9)0.0021 (7)0.0150 (7)0.0019 (7)
C100.0513 (9)0.0348 (8)0.0616 (10)0.0022 (6)0.0042 (7)0.0031 (7)
C110.0598 (12)0.0565 (11)0.1171 (18)0.0099 (9)0.0145 (11)0.0042 (11)
C120.1015 (16)0.0535 (11)0.0655 (12)0.0066 (10)0.0007 (11)0.0114 (9)
C130.0499 (9)0.0376 (8)0.0500 (9)0.0013 (7)0.0133 (7)0.0026 (7)
C140.0562 (10)0.0592 (10)0.0500 (9)0.0100 (8)0.0098 (8)0.0068 (8)
C150.0598 (10)0.0443 (9)0.0617 (10)0.0150 (7)0.0243 (8)0.0105 (7)
C160.0591 (10)0.0362 (8)0.0530 (9)0.0066 (7)0.0176 (7)0.0018 (6)
C170.0771 (13)0.0465 (10)0.0849 (13)0.0090 (9)0.0152 (10)0.0028 (9)
C180.0844 (14)0.0671 (12)0.0692 (12)0.0189 (10)0.0301 (10)0.0039 (10)
Geometric parameters (Å, º) top
O1—C11.2317 (19)C6—H6C0.9600
O2—C31.2031 (18)C7—C101.517 (2)
O3—C91.2018 (18)C8—C91.502 (2)
O4—C71.2270 (18)C8—H8A0.9700
O5—C151.2016 (19)C8—H8B0.9700
O6—C131.2326 (18)C9—C101.518 (2)
N1—C11.329 (2)C10—C121.520 (3)
N1—C21.445 (2)C10—C111.533 (3)
N1—H1A0.8600C11—H11A0.9600
N2—C71.334 (2)C11—H11B0.9600
N2—C81.4503 (19)C11—H11C0.9600
N2—H2C0.8600C12—H12A0.9600
N3—C131.3318 (19)C12—H12B0.9600
N3—C141.451 (2)C12—H12C0.9600
N3—H3A0.8600C13—C161.517 (2)
C1—C41.514 (2)C14—C151.508 (2)
C2—C31.503 (2)C14—H14A0.9700
C2—H2A0.9700C14—H14B0.9700
C2—H2B0.9700C15—C161.516 (2)
C3—C41.515 (2)C16—C171.517 (2)
C4—C61.522 (2)C16—C181.536 (2)
C4—C51.532 (2)C17—H17A0.9600
C5—H5A0.9600C17—H17B0.9600
C5—H5B0.9600C17—H17C0.9600
C5—H5C0.9600C18—H18A0.9600
C6—H6A0.9600C18—H18B0.9600
C6—H6B0.9600C18—H18C0.9600
C1—N1—C2115.32 (13)C8—C9—C10109.26 (12)
C1—N1—H1A122.3C7—C10—C9102.63 (12)
C2—N1—H1A122.3C7—C10—C12112.43 (15)
C7—N2—C8115.10 (12)C9—C10—C12112.74 (15)
C7—N2—H2C122.4C7—C10—C11108.58 (14)
C8—N2—H2C122.4C9—C10—C11107.67 (15)
C13—N3—C14114.88 (13)C12—C10—C11112.24 (16)
C13—N3—H3A122.6C10—C11—H11A109.5
C14—N3—H3A122.6C10—C11—H11B109.5
O1—C1—N1125.42 (15)H11A—C11—H11B109.5
O1—C1—C4124.62 (15)C10—C11—H11C109.5
N1—C1—C4109.96 (13)H11A—C11—H11C109.5
N1—C2—C3102.68 (13)H11B—C11—H11C109.5
N1—C2—H2A111.2C10—C12—H12A109.5
C3—C2—H2A111.2C10—C12—H12B109.5
N1—C2—H2B111.2H12A—C12—H12B109.5
C3—C2—H2B111.2C10—C12—H12C109.5
H2A—C2—H2B109.1H12A—C12—H12C109.5
O2—C3—C2124.16 (16)H12B—C12—H12C109.5
O2—C3—C4126.25 (15)O6—C13—N3124.92 (14)
C2—C3—C4109.59 (12)O6—C13—C16125.32 (14)
C1—C4—C3102.29 (12)N3—C13—C16109.76 (13)
C1—C4—C6110.86 (13)N3—C14—C15102.64 (13)
C3—C4—C6111.87 (14)N3—C14—H14A111.2
C1—C4—C5110.42 (14)C15—C14—H14A111.2
C3—C4—C5109.85 (13)N3—C14—H14B111.2
C6—C4—C5111.21 (15)C15—C14—H14B111.2
C4—C5—H5A109.5H14A—C14—H14B109.2
C4—C5—H5B109.5O5—C15—C14124.70 (16)
H5A—C5—H5B109.5O5—C15—C16126.18 (16)
C4—C5—H5C109.5C14—C15—C16109.11 (13)
H5A—C5—H5C109.5C15—C16—C13101.93 (13)
H5B—C5—H5C109.5C15—C16—C17113.48 (14)
C4—C6—H6A109.5C13—C16—C17113.27 (13)
C4—C6—H6B109.5C15—C16—C18107.89 (13)
H6A—C6—H6B109.5C13—C16—C18108.59 (14)
C4—C6—H6C109.5C17—C16—C18111.16 (15)
H6A—C6—H6C109.5C16—C17—H17A109.5
H6B—C6—H6C109.5C16—C17—H17B109.5
O4—C7—N2125.33 (14)H17A—C17—H17B109.5
O4—C7—C10125.02 (14)C16—C17—H17C109.5
N2—C7—C10109.64 (13)H17A—C17—H17C109.5
N2—C8—C9103.05 (12)H17B—C17—H17C109.5
N2—C8—H8A111.2C16—C18—H18A109.5
C9—C8—H8A111.2C16—C18—H18B109.5
N2—C8—H8B111.2H18A—C18—H18B109.5
C9—C8—H8B111.2C16—C18—H18C109.5
H8A—C8—H8B109.1H18A—C18—H18C109.5
O3—C9—C8124.60 (15)H18B—C18—H18C109.5
O3—C9—C10126.13 (15)
C2—N1—C1—O1179.55 (16)O4—C7—C10—C1170.0 (2)
C2—N1—C1—C40.1 (2)N2—C7—C10—C11108.80 (17)
C1—N1—C2—C32.50 (19)O3—C9—C10—C7175.50 (17)
N1—C2—C3—O2175.96 (16)C8—C9—C10—C75.59 (18)
N1—C2—C3—C43.87 (17)O3—C9—C10—C1254.3 (2)
O1—C1—C4—C3177.14 (16)C8—C9—C10—C12126.78 (16)
N1—C1—C4—C32.31 (17)O3—C9—C10—C1170.0 (2)
O1—C1—C4—C657.7 (2)C8—C9—C10—C11108.87 (15)
N1—C1—C4—C6121.72 (16)C14—N3—C13—O6173.29 (16)
O1—C1—C4—C566.0 (2)C14—N3—C13—C167.15 (19)
N1—C1—C4—C5114.57 (16)C13—N3—C14—C151.25 (18)
O2—C3—C4—C1176.02 (17)N3—C14—C15—O5171.59 (16)
C2—C3—C4—C13.81 (16)N3—C14—C15—C169.12 (17)
O2—C3—C4—C657.3 (2)O5—C15—C16—C13168.00 (17)
C2—C3—C4—C6122.51 (15)C14—C15—C16—C1312.73 (17)
O2—C3—C4—C566.7 (2)O5—C15—C16—C1745.9 (2)
C2—C3—C4—C5113.47 (16)C14—C15—C16—C17134.87 (15)
C8—N2—C7—O4178.53 (17)O5—C15—C16—C1877.8 (2)
C8—N2—C7—C102.7 (2)C14—C15—C16—C18101.51 (16)
C7—N2—C8—C91.00 (19)O6—C13—C16—C15168.38 (16)
N2—C8—C9—O3176.84 (17)N3—C13—C16—C1512.06 (17)
N2—C8—C9—C104.24 (18)O6—C13—C16—C1746.1 (2)
O4—C7—C10—C9176.17 (17)N3—C13—C16—C17134.34 (15)
N2—C7—C10—C95.01 (18)O6—C13—C16—C1877.9 (2)
O4—C7—C10—C1254.8 (2)N3—C13—C16—C18101.66 (16)
N2—C7—C10—C12126.40 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.861.992.8433 (19)171
N2—H2C···O6ii0.862.183.0023 (18)161
N3—H3A···O4iii0.862.042.8814 (18)166
C2—H2A···O60.972.593.287 (2)129
C5—H5C···O3iv0.962.583.511 (3)163
C8—H8A···O5v0.972.563.337 (2)137
C17—H17C···O2vi0.962.543.369 (3)145
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+1, z; (iii) x, y1, z; (iv) x+1/2, y1/2, z+1/2; (v) x, y+1, z1/2; (vi) x, y, z+1/2.
 

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