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In the title compound, C9H15Br2NO, the piperidin-4-one ring adopts a chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004291/hb2280sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004291/hb2280IIsup2.hkl
Contains datablock II

CCDC reference: 636669

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.043
  • wR factor = 0.090
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O1 .. 2.64 Ang.
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 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one top
Crystal data top
C9H15Br2NOF(000) = 616
Mr = 313.04Dx = 1.866 Mg m3
Monoclinic, P21/cMelting point: 418 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.8677 (18) ÅCell parameters from 2481 reflections
b = 21.968 (4) Åθ = 1.9–27.9°
c = 6.0078 (12) ŵ = 7.24 mm1
β = 107.78 (3)°T = 293 K
V = 1114.5 (4) Å3Prism, colorless
Z = 40.34 × 0.18 × 0.16 mm
Data collection top
Rigaku Saturn
diffractometer
2181 independent reflections
Radiation source: fine-focus sealed tube1667 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 1010
Absorption correction: multi-scan
(Jacobson, 1998)
k = 2726
Tmin = 0.210, Tmax = 0.314l = 77
8984 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)] = 0.043Hydrogen site location: difmap and geom
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0326P)2]
where P = (Fo2 + 2Fc2)/3
2181 reflections(Δ/σ)max = 0.001
125 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.86 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
Br10.28910 (6)0.69608 (2)0.51709 (7)0.02095 (17)
Br20.96036 (6)0.69423 (2)0.78746 (8)0.02360 (17)
C10.4766 (5)0.60658 (19)0.8549 (7)0.0154 (10)
C20.4816 (5)0.67247 (19)0.7597 (7)0.0145 (10)
H20.49400.70040.89120.017*
C30.6244 (5)0.68036 (19)0.6778 (7)0.0153 (10)
C40.7770 (5)0.6713 (2)0.8802 (7)0.0187 (10)
H40.77250.69861.00690.022*
C50.7819 (5)0.6045 (2)0.9732 (7)0.0172 (10)
C60.3557 (5)0.6041 (2)0.9900 (7)0.0258 (12)
H6A0.35510.56401.05340.039*
H6B0.25240.61340.88650.039*
H6C0.38400.63321.11500.039*
C70.4316 (6)0.55958 (19)0.6588 (8)0.0223 (11)
H7A0.49360.56610.55500.033*
H7B0.32120.56360.57370.033*
H7C0.45160.51940.72430.033*
C80.8095 (6)0.5589 (2)0.8001 (8)0.0250 (11)
H8A0.78910.51850.84500.037*
H8B0.91730.56160.79890.037*
H8C0.73960.56770.64670.037*
C90.9144 (5)0.5988 (2)1.2049 (7)0.0294 (12)
H9A0.89920.62861.31310.044*
H9B1.01470.60551.17910.044*
H9C0.91240.55881.26800.044*
N10.6323 (5)0.59331 (17)1.0261 (6)0.0188 (9)
H1A0.633 (5)0.613 (2)1.150 (7)0.028*
O10.6210 (4)0.69118 (14)0.4778 (5)0.0240 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0139 (3)0.0215 (3)0.0246 (3)0.0026 (2)0.0016 (2)0.00371 (19)
Br20.0144 (3)0.0210 (3)0.0355 (3)0.0024 (2)0.0078 (2)0.0004 (2)
C10.013 (3)0.015 (2)0.015 (2)0.001 (2)0.0012 (19)0.0024 (19)
C20.011 (2)0.012 (2)0.017 (2)0.0008 (19)0.0010 (18)0.0026 (18)
C30.014 (3)0.007 (2)0.024 (3)0.0012 (19)0.003 (2)0.0002 (18)
C40.013 (3)0.028 (3)0.017 (2)0.003 (2)0.0065 (19)0.001 (2)
C50.014 (3)0.018 (3)0.017 (2)0.001 (2)0.0013 (19)0.0028 (19)
C60.022 (3)0.030 (3)0.024 (3)0.004 (2)0.004 (2)0.003 (2)
C70.019 (3)0.012 (2)0.031 (3)0.000 (2)0.001 (2)0.000 (2)
C80.024 (3)0.019 (3)0.033 (3)0.000 (2)0.009 (2)0.001 (2)
C90.016 (3)0.039 (3)0.030 (3)0.001 (2)0.004 (2)0.001 (2)
N10.017 (2)0.023 (2)0.0151 (19)0.0012 (19)0.0032 (17)0.0015 (17)
O10.017 (2)0.030 (2)0.0248 (19)0.0018 (15)0.0050 (15)0.0089 (14)
Geometric parameters (Å, º) top
C2—Br11.946 (4)C5—C91.528 (6)
C4—Br21.940 (5)C6—H6A0.9600
C1—N11.478 (5)C6—H6B0.9600
C1—C71.525 (6)C6—H6C0.9600
C1—C61.530 (6)C7—H7A0.9600
C1—C21.562 (6)C7—H7B0.9600
C2—C31.502 (6)C7—H7C0.9600
C2—H20.9800C8—H8A0.9600
C3—O11.216 (5)C8—H8B0.9600
C3—C41.532 (6)C8—H8C0.9600
C4—C51.566 (6)C9—H9A0.9600
C4—H40.9800C9—H9B0.9600
C5—N11.475 (5)C9—H9C0.9600
C5—C81.517 (6)N1—H1A0.86 (4)
N1—C1—C7111.9 (4)C1—C6—H6A109.5
N1—C1—C6106.3 (3)C1—C6—H6B109.5
C7—C1—C6109.0 (4)H6A—C6—H6B109.5
N1—C1—C2108.2 (3)C1—C6—H6C109.5
C7—C1—C2112.0 (3)H6A—C6—H6C109.5
C6—C1—C2109.3 (4)H6B—C6—H6C109.5
C3—C2—C1110.4 (4)C1—C7—H7A109.5
C3—C2—Br1111.0 (3)C1—C7—H7B109.5
C1—C2—Br1113.9 (3)H7A—C7—H7B109.5
C3—C2—H2107.1C1—C7—H7C109.5
C1—C2—H2107.1H7A—C7—H7C109.5
Br1—C2—H2107.1H7B—C7—H7C109.5
O1—C3—C2125.3 (4)C5—C8—H8A109.5
O1—C3—C4124.0 (4)C5—C8—H8B109.5
C2—C3—C4110.7 (3)H8A—C8—H8B109.5
C3—C4—C5109.1 (4)C5—C8—H8C109.5
C3—C4—Br2110.7 (3)H8A—C8—H8C109.5
C5—C4—Br2114.3 (3)H8B—C8—H8C109.5
C3—C4—H4107.5C5—C9—H9A109.5
C5—C4—H4107.5C5—C9—H9B109.5
Br2—C4—H4107.5H9A—C9—H9B109.5
N1—C5—C8112.4 (4)C5—C9—H9C109.5
N1—C5—C9106.4 (3)H9A—C9—H9C109.5
C8—C5—C9109.3 (4)H9B—C9—H9C109.5
N1—C5—C4107.7 (4)C5—N1—C1121.9 (3)
C8—C5—C4111.5 (3)C5—N1—H1A110 (3)
C9—C5—C4109.3 (4)C1—N1—H1A105 (3)
N1—C1—C2—C351.0 (4)C2—C3—C4—Br2170.8 (3)
C7—C1—C2—C372.8 (4)C3—C4—C5—N153.0 (4)
C6—C1—C2—C3166.4 (3)Br2—C4—C5—N1177.5 (3)
N1—C1—C2—Br1176.6 (3)C3—C4—C5—C870.8 (5)
C7—C1—C2—Br152.8 (4)Br2—C4—C5—C853.7 (4)
C6—C1—C2—Br168.0 (4)C3—C4—C5—C9168.2 (4)
C1—C2—C3—O1117.0 (4)Br2—C4—C5—C967.3 (4)
Br1—C2—C3—O110.3 (5)C8—C5—N1—C172.5 (5)
C1—C2—C3—C461.5 (4)C9—C5—N1—C1167.9 (4)
Br1—C2—C3—C4171.2 (3)C4—C5—N1—C150.8 (5)
O1—C3—C4—C5115.9 (5)C7—C1—N1—C574.5 (5)
C2—C3—C4—C562.6 (4)C6—C1—N1—C5166.6 (4)
O1—C3—C4—Br210.7 (5)C2—C1—N1—C549.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1a···O1i0.86 (4)2.64 (4)3.488 (6)169 (6)
Symmetry code: (i) x, y, z+1.
 

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