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The title compound, C13H21N2O+·Br, was crystallized from a CH2Cl2 solution of N2,N2-dibenzyl-N,N,2-trimethyl­alanin­amide and BBr3. The geometry of the cation is unexceptional. Inter­molecular N—H...O and N—H...Br hydrogen bonds link two cations and two anions into a hydrogen-bonded cluster. The crystal packing is further stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023026/cv2066sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023026/cv2066Isup2.hkl
Contains datablock I

CCDC reference: 613651

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C)= 0.006 Å
  • R factor = 0.058
  • wR factor = 0.108
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: maXus (Mackay et al., 1999).

N-benzyl-1-(dimethylamino)-2-methyl-1-oxopropan-2-aminium bromide top
Crystal data top
C13H21N2O+·BrF(000) = 1248
Mr = 301.23Dx = 1.410 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 110 reflections
a = 15.7845 (8) Åθ = 3.3–20.7°
b = 10.6592 (14) ŵ = 2.88 mm1
c = 16.872 (2) ÅT = 299 K
V = 2838.7 (5) Å3Block, colourless
Z = 80.33 × 0.30 × 0.27 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
1828 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.099
φ scansθmax = 27.5°, θmin = 4.5°
Absorption correction: numerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
h = 2018
Tmin = 0.476, Tmax = 0.567k = 1313
18982 measured reflectionsl = 2121
3239 independent 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)] = 0.058H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.014P)2 + 6.423P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3239 reflectionsΔρmax = 0.67 e Å3
154 parametersΔρmin = 0.64 e Å3
0 restraints
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
Br10.62320 (3)0.83222 (4)0.32683 (4)0.0646 (2)
C10.3879 (2)0.6389 (4)0.3590 (2)0.0352 (9)
C20.3915 (3)0.7537 (4)0.3966 (3)0.0456 (11)
H20.44330.79400.40270.055*
C30.3187 (3)0.8088 (4)0.4254 (3)0.0567 (13)
H30.32190.88500.45210.068*
C40.2416 (3)0.7519 (5)0.4147 (3)0.0613 (13)
H40.19250.78980.43340.074*
C50.2372 (3)0.6391 (5)0.3763 (3)0.0593 (14)
H50.18500.60080.36850.071*
C60.3096 (3)0.5824 (4)0.3495 (2)0.0460 (11)
H60.30610.50480.32450.055*
C70.4647 (2)0.5766 (4)0.3255 (2)0.0405 (10)
H7A0.45480.48790.30800.049*
H7B0.48560.62640.27900.049*
C80.5975 (2)0.4658 (3)0.3755 (2)0.0312 (9)
C90.6283 (3)0.4620 (4)0.2903 (2)0.0471 (11)
H9A0.58280.43610.25630.071*
H9B0.67430.40360.28580.071*
H9C0.64730.54400.27480.071*
C100.6694 (2)0.4922 (4)0.4337 (2)0.0397 (10)
H10A0.68980.57610.42590.060*
H10B0.71470.43370.42480.060*
H10C0.64890.48330.48700.060*
C110.5454 (2)0.3526 (3)0.4061 (2)0.0278 (8)
C130.5119 (3)0.1349 (4)0.4163 (3)0.0560 (13)
H13A0.46110.17040.43810.084*
H13B0.54020.08610.45620.084*
H13C0.49770.08200.37220.084*
C120.6474 (3)0.1957 (4)0.3539 (3)0.0511 (12)
H12A0.64460.20740.29750.077*
H12B0.65700.10870.36550.077*
H12C0.69300.24490.37510.077*
N10.53735 (19)0.5753 (3)0.38318 (18)0.0299 (7)
H1A0.57050.64620.37190.036*
H1B0.51300.57700.43310.036*
N20.56786 (19)0.2355 (3)0.3896 (2)0.0359 (8)
O10.48182 (16)0.3757 (2)0.44705 (16)0.0370 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0550 (3)0.0376 (2)0.1012 (4)0.0029 (2)0.0089 (3)0.0174 (3)
C10.036 (2)0.041 (2)0.029 (2)0.0088 (18)0.0038 (18)0.0018 (18)
C20.044 (3)0.040 (2)0.054 (3)0.002 (2)0.002 (2)0.000 (2)
C30.058 (3)0.048 (3)0.063 (3)0.016 (2)0.004 (3)0.012 (3)
C40.045 (3)0.074 (3)0.065 (3)0.023 (3)0.003 (3)0.005 (3)
C50.035 (3)0.085 (4)0.058 (3)0.005 (2)0.001 (2)0.010 (3)
C60.043 (3)0.054 (3)0.041 (3)0.001 (2)0.002 (2)0.007 (2)
C70.044 (2)0.047 (2)0.031 (2)0.0100 (19)0.005 (2)0.004 (2)
C80.029 (2)0.0301 (19)0.034 (2)0.0045 (16)0.0054 (17)0.0004 (18)
C90.052 (3)0.049 (2)0.041 (2)0.010 (2)0.017 (2)0.007 (2)
C100.030 (2)0.039 (2)0.050 (3)0.0006 (18)0.001 (2)0.003 (2)
C110.030 (2)0.030 (2)0.024 (2)0.0002 (16)0.0038 (17)0.0023 (17)
C130.053 (3)0.032 (2)0.083 (4)0.009 (2)0.003 (3)0.004 (2)
C120.042 (3)0.041 (2)0.071 (3)0.0097 (19)0.004 (2)0.012 (2)
N10.0315 (18)0.0292 (16)0.0290 (18)0.0003 (13)0.0033 (14)0.0002 (15)
N20.0319 (18)0.0278 (17)0.048 (2)0.0021 (14)0.0029 (16)0.0035 (16)
O10.0361 (16)0.0341 (14)0.0408 (17)0.0027 (12)0.0122 (13)0.0031 (13)
Geometric parameters (Å, º) top
C1—C21.379 (6)C9—H9A0.9600
C1—C61.385 (6)C9—H9B0.9600
C1—C71.493 (5)C9—H9C0.9600
C2—C31.379 (6)C10—H10A0.9600
C2—H20.9300C10—H10B0.9600
C3—C41.372 (7)C10—H10C0.9600
C3—H30.9300C11—O11.242 (4)
C4—C51.366 (7)C11—N21.327 (5)
C4—H40.9300C13—N21.461 (5)
C5—C61.370 (6)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C6—H60.9300C13—H13C0.9600
C7—N11.503 (5)C12—N21.456 (5)
C7—H7A1.00C12—H12A0.9600
C7—H7B1.00C12—H12B0.9600
C8—N11.509 (4)C12—H12C0.9600
C8—C91.519 (5)N1—H1A0.94
C8—C101.527 (5)N1—H1B0.93
C8—C111.549 (5)
C2—C1—C6118.4 (4)C8—C9—H9C109.5
C2—C1—C7122.4 (4)H9A—C9—H9C109.5
C6—C1—C7119.2 (4)H9B—C9—H9C109.5
C3—C2—C1120.4 (4)C8—C10—H10A109.5
C3—C2—H2119.8C8—C10—H10B109.5
C1—C2—H2119.8H10A—C10—H10B109.5
C4—C3—C2120.3 (4)C8—C10—H10C109.5
C4—C3—H3119.9H10A—C10—H10C109.5
C2—C3—H3119.9H10B—C10—H10C109.5
C5—C4—C3119.8 (4)O1—C11—N2121.3 (3)
C5—C4—H4120.1O1—C11—C8117.3 (3)
C3—C4—H4120.1N2—C11—C8121.4 (3)
C4—C5—C6120.2 (5)N2—C13—H13A109.5
C4—C5—H5119.9N2—C13—H13B109.5
C6—C5—H5119.9H13A—C13—H13B109.5
C5—C6—C1120.9 (4)N2—C13—H13C109.5
C5—C6—H6119.5H13A—C13—H13C109.5
C1—C6—H6119.5H13B—C13—H13C109.5
C1—C7—N1112.3 (3)N2—C12—H12A109.5
C1—C7—H7A113.9N2—C12—H12B109.5
N1—C7—H7A107.5H12A—C12—H12B109.5
C1—C7—H7B109.1N2—C12—H12C109.5
N1—C7—H7B105.1H12A—C12—H12C109.5
H7A—C7—H7B108.6H12B—C12—H12C109.5
N1—C8—C9107.6 (3)C7—N1—C8115.6 (3)
N1—C8—C10105.7 (3)C7—N1—H1A106.7
C9—C8—C10112.1 (3)C8—N1—H1A104.7
N1—C8—C11103.9 (3)C7—N1—H1B105.8
C9—C8—C11117.7 (3)C8—N1—H1B110.7
C10—C8—C11108.9 (3)H1A—N1—H1B113.6
C8—C9—H9A109.5C11—N2—C12126.3 (3)
C8—C9—H9B109.5C11—N2—C13117.7 (3)
H9A—C9—H9B109.5C12—N2—C13115.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br10.942.283.201 (3)166
N1—H1B···O1i0.932.092.927 (4)151
Symmetry code: (i) x+1, y+1, z+1.
 

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