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In the title compound, C11H20N2O3, the pyrrolidine ring adopts an envelope conformation, where the acet­oxy and carbamoyl groups are equatorial. Each mol­ecule inter­acts, through strong N—H...O hydrogen bonds, with two adjacent mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029849/ez2016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029849/ez2016Isup2.hkl
Contains datablock I

CCDC reference: 620957

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.146
  • Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.61 mm PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C11 .. 6.65 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3-Carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yl acetate top
Crystal data top
C11H20N2O3F(000) = 496
Mr = 228.29Dx = 1.137 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.7037 (19) ÅCell parameters from 12633 reflections
b = 11.706 (2) Åθ = 2.4–27.5°
c = 12.293 (3) ŵ = 0.08 mm1
β = 107.27 (3)°T = 293 K
V = 1333.4 (5) Å3Platelet, colorless
Z = 40.61 × 0.52 × 0.21 mm
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
3056 independent reflections
Radiation source: Rotating Anode1787 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω scansh = 1212
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1515
Tmin = 0.951, Tmax = 0.983l = 1515
12633 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0805P)2]
where P = (Fo2 + 2Fc2)/3
3056 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 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
O10.00760 (12)0.52425 (9)0.28945 (8)0.0635 (3)
O20.01639 (19)0.35524 (11)0.21026 (13)0.0981 (5)
O30.1009 (2)0.92166 (11)0.07561 (13)0.1089 (6)
N10.07550 (12)0.56922 (11)0.17698 (9)0.0544 (3)
N20.01157 (18)0.84928 (12)0.05732 (12)0.0802 (5)
H2A0.01070.91590.07630.096*
H2B0.00640.78960.09160.096*
C10.01033 (17)0.66580 (13)0.15479 (13)0.0589 (4)
C20.10708 (17)0.71866 (13)0.05381 (12)0.0612 (4)
H2C0.11970.67010.01340.073*
C30.24303 (19)0.71151 (18)0.09190 (14)0.0779 (5)
H3A0.32800.70410.02640.093*
H3B0.25300.77970.13380.093*
C40.22553 (16)0.60572 (15)0.16839 (13)0.0636 (4)
C50.03184 (19)0.41355 (15)0.29158 (15)0.0672 (4)
C60.0979 (2)0.37803 (19)0.41253 (17)0.0960 (7)
H6A0.12560.29910.41500.144*
H6B0.02900.38810.45390.144*
H6C0.18150.42410.44640.144*
C70.1365 (2)0.61634 (16)0.11950 (19)0.0830 (6)
H7A0.10030.56430.05710.125*
H7B0.20040.57640.18280.125*
H7C0.18790.67720.09640.125*
C80.0678 (2)0.74819 (16)0.25499 (16)0.0841 (6)
H8A0.01150.77900.27720.126*
H8B0.11940.80930.23250.126*
H8C0.13150.70790.31810.126*
C90.0736 (2)0.83861 (14)0.02482 (15)0.0712 (5)
C100.2534 (2)0.6343 (2)0.28045 (17)0.0946 (7)
H10A0.24240.56660.32640.142*
H10B0.34980.66310.26580.142*
H10C0.18570.69110.32010.142*
C110.3225 (2)0.5070 (2)0.1124 (2)0.1086 (8)
H11A0.30610.44330.16380.163*
H11B0.30090.48520.04390.163*
H11C0.42160.53020.09400.163*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0782 (7)0.0618 (7)0.0484 (5)0.0114 (6)0.0153 (5)0.0026 (5)
O20.1463 (14)0.0688 (8)0.0843 (9)0.0109 (8)0.0420 (9)0.0156 (7)
O30.1916 (16)0.0631 (7)0.1144 (11)0.0129 (9)0.1106 (12)0.0029 (7)
N10.0592 (7)0.0619 (7)0.0442 (6)0.0011 (6)0.0188 (5)0.0015 (5)
N20.1271 (14)0.0597 (8)0.0782 (9)0.0029 (8)0.0680 (9)0.0012 (7)
C10.0623 (9)0.0568 (9)0.0630 (9)0.0062 (7)0.0268 (7)0.0077 (7)
C20.0767 (10)0.0627 (9)0.0537 (8)0.0009 (8)0.0339 (7)0.0012 (7)
C30.0697 (11)0.1043 (14)0.0671 (10)0.0125 (10)0.0317 (8)0.0250 (10)
C40.0581 (9)0.0834 (11)0.0550 (8)0.0032 (8)0.0257 (7)0.0107 (8)
C50.0714 (10)0.0639 (10)0.0718 (10)0.0084 (9)0.0296 (8)0.0015 (9)
C60.1057 (16)0.0924 (14)0.0831 (13)0.0322 (12)0.0177 (11)0.0161 (11)
C70.0726 (11)0.0754 (11)0.1159 (15)0.0066 (9)0.0508 (11)0.0101 (11)
C80.0957 (13)0.0727 (11)0.0812 (12)0.0129 (10)0.0222 (10)0.0203 (10)
C90.0997 (13)0.0630 (10)0.0683 (10)0.0038 (9)0.0514 (9)0.0002 (8)
C100.1002 (15)0.1256 (17)0.0781 (12)0.0339 (13)0.0571 (11)0.0286 (12)
C110.0667 (12)0.134 (2)0.1232 (17)0.0249 (13)0.0253 (11)0.0050 (16)
Geometric parameters (Å, º) top
O1—C51.349 (2)C4—C101.518 (2)
O1—N11.4429 (15)C4—C111.520 (3)
O2—C51.183 (2)C5—C61.493 (3)
O3—C91.226 (2)C6—H6A0.9600
N1—C11.4769 (19)C6—H6B0.9600
N1—C41.491 (2)C6—H6C0.9600
N2—C91.326 (2)C7—H7A0.9600
N2—H2A0.8600C7—H7B0.9600
N2—H2B0.8600C7—H7C0.9600
C1—C71.529 (2)C8—H8A0.9600
C1—C81.533 (2)C8—H8B0.9600
C1—C21.543 (2)C8—H8C0.9600
C2—C91.508 (2)C10—H10A0.9600
C2—C31.528 (2)C10—H10B0.9600
C2—H2C0.9800C10—H10C0.9600
C3—C41.534 (2)C11—H11A0.9600
C3—H3A0.9700C11—H11B0.9600
C3—H3B0.9700C11—H11C0.9600
C5—O1—N1114.53 (12)C5—C6—H6A109.5
O1—N1—C1109.52 (11)C5—C6—H6B109.5
O1—N1—C4109.32 (10)H6A—C6—H6B109.5
C1—N1—C4111.10 (12)C5—C6—H6C109.5
C9—N2—H2A120.0H6A—C6—H6C109.5
C9—N2—H2B120.0H6B—C6—H6C109.5
H2A—N2—H2B120.0C1—C7—H7A109.5
N1—C1—C7107.79 (13)C1—C7—H7B109.5
N1—C1—C8115.07 (13)H7A—C7—H7B109.5
C7—C1—C8109.60 (15)C1—C7—H7C109.5
N1—C1—C297.67 (12)H7A—C7—H7C109.5
C7—C1—C2112.68 (14)H7B—C7—H7C109.5
C8—C1—C2113.55 (14)C1—C8—H8A109.5
C9—C2—C3112.95 (14)C1—C8—H8B109.5
C9—C2—C1113.83 (14)H8A—C8—H8B109.5
C3—C2—C1103.29 (12)C1—C8—H8C109.5
C9—C2—H2C108.8H8A—C8—H8C109.5
C3—C2—H2C108.8H8B—C8—H8C109.5
C1—C2—H2C108.8O3—C9—N2121.92 (16)
C2—C3—C4106.48 (14)O3—C9—C2121.57 (14)
C2—C3—H3A110.4N2—C9—C2116.50 (14)
C4—C3—H3A110.4C4—C10—H10A109.5
C2—C3—H3B110.4C4—C10—H10B109.5
C4—C3—H3B110.4H10A—C10—H10B109.5
H3A—C3—H3B108.6C4—C10—H10C109.5
N1—C4—C10115.63 (14)H10A—C10—H10C109.5
N1—C4—C11105.92 (15)H10B—C10—H10C109.5
C10—C4—C11109.00 (18)C4—C11—H11A109.5
N1—C4—C3101.70 (12)C4—C11—H11B109.5
C10—C4—C3111.19 (16)H11A—C11—H11B109.5
C11—C4—C3113.27 (16)C4—C11—H11C109.5
O2—C5—O1125.01 (17)H11A—C11—H11C109.5
O2—C5—C6126.19 (18)H11B—C11—H11C109.5
O1—C5—C6108.80 (15)
C5—O1—N1—C1119.93 (15)O1—N1—C4—C1023.8 (2)
C5—O1—N1—C4118.13 (14)C1—N1—C4—C1097.22 (18)
O1—N1—C1—C780.73 (15)O1—N1—C4—C1197.05 (16)
C4—N1—C1—C7158.40 (13)C1—N1—C4—C11141.97 (14)
O1—N1—C1—C841.88 (17)O1—N1—C4—C3144.36 (12)
C4—N1—C1—C878.99 (17)C1—N1—C4—C323.37 (16)
O1—N1—C1—C2162.41 (10)C2—C3—C4—N15.67 (17)
C4—N1—C1—C241.54 (13)C2—C3—C4—C10129.32 (16)
N1—C1—C2—C9165.01 (12)C2—C3—C4—C11107.53 (18)
C7—C1—C2—C982.02 (17)N1—O1—C5—O21.2 (2)
C8—C1—C2—C943.34 (18)N1—O1—C5—C6179.05 (14)
N1—C1—C2—C342.16 (15)C3—C2—C9—O333.6 (3)
C7—C1—C2—C3155.13 (15)C1—C2—C9—O383.8 (2)
C8—C1—C2—C379.51 (18)C3—C2—C9—N2147.26 (17)
C9—C2—C3—C4154.05 (15)C1—C2—C9—N295.4 (2)
C1—C2—C3—C430.62 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.862.092.929 (2)164
N2—H2B···O2ii0.862.203.0359 (19)163
Symmetry codes: (i) x, y+2, z; (ii) x, y+1, z.
 

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