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All interatomic distances of the title compound, C5H12N+·Cl, are normal. All C atoms lie in a common plane. Molecules of the title compound are assembled by intermolecular weak N—H...Cl hydrogen bonds into an infinite zigzag ribbon structure along the y axis. The ribbon is bent repeatedly with angles of 34.15 (6)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008108/bt6048sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008108/bt6048Isup2.hkl
Contains datablock I

CCDC reference: 170300

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.139
  • Data-to-parameter ratio = 18.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.13 From the CIF: _reflns_number_total 1241 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1312 Completeness (_total/calc) 94.59% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CrysAlis CCD (UNIL IC & Kuma,2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) andORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.

(3-Methylbut-2-enyl)ammonium chloride top
Crystal data top
C5H12N+·ClF(000) = 264
Mr = 121.61Dx = 1.102 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.1286 (12) ÅCell parameters from 2025 reflections
b = 5.8874 (7) Åθ = 5–22°
c = 8.8335 (9) ŵ = 0.42 mm1
β = 94.321 (8)°T = 291 K
V = 732.69 (13) Å3Plate, colourless
Z = 40.44 × 0.25 × 0.04 mm
Data collection top
Kuma KM4-CCD
diffractometer
1241 independent reflections
Radiation source: fine-focus sealed tube1223 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 25.1°, θmin = 3.8°
Absorption correction: numerical
(X-RED; Stoe & Cie, 1999)
h = 1616
Tmin = 0.837, Tmax = 0.983k = 75
7034 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.2647P]
where P = (Fo2 + 2Fc2)/3
1241 reflections(Δ/σ)max = 0.001
66 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.18 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
Cl10.08877 (4)0.25531 (7)0.56750 (6)0.0435 (3)
N10.08159 (14)0.2554 (2)0.7868 (2)0.0433 (5)
H1A0.03060.25730.73330.065*
H1B0.07980.13270.84580.065*
H1C0.08210.37950.84420.065*
C10.16857 (19)0.2496 (3)0.6816 (3)0.0496 (6)
H1D0.16740.11560.61790.060*
H1E0.16990.38210.61620.060*
C20.25574 (19)0.2462 (3)0.7669 (3)0.0508 (6)
H20.26370.12080.82870.061*
C30.32232 (17)0.4016 (4)0.7638 (3)0.0621 (7)
C40.3200 (2)0.6189 (5)0.6750 (5)0.0925 (11)
H4A0.26120.62900.62770.139*
H4B0.32550.74560.74210.139*
H4C0.37200.62090.59840.139*
C50.4071 (2)0.3760 (8)0.8573 (5)0.1029 (12)
H5A0.40430.23120.90730.154*
H5B0.46440.38580.79210.154*
H5C0.40630.49480.93180.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0506 (4)0.0305 (4)0.0504 (4)0.00036 (17)0.0112 (3)0.00028 (17)
N10.0484 (11)0.0327 (10)0.0503 (11)0.0011 (6)0.0146 (9)0.0007 (6)
C10.0598 (15)0.0448 (14)0.0449 (13)0.0041 (8)0.0081 (11)0.0012 (8)
C20.0487 (13)0.0428 (14)0.0607 (15)0.0058 (8)0.0028 (11)0.0030 (9)
C30.0517 (13)0.0588 (15)0.0761 (17)0.0045 (11)0.0064 (12)0.0127 (12)
C40.081 (2)0.0606 (18)0.137 (3)0.0132 (15)0.015 (2)0.0048 (18)
C50.0607 (19)0.122 (3)0.130 (3)0.0042 (17)0.0281 (19)0.003 (2)
Geometric parameters (Å, º) top
N1—C11.484 (3)C3—C41.502 (4)
N1—H1A0.8900C3—C51.513 (4)
N1—H1B0.8900C4—H4A0.9600
N1—H1C0.8900C4—H4B0.9600
C1—C21.492 (4)C4—H4C0.9600
C1—H1D0.9700C5—H5A0.9600
C1—H1E0.9700C5—H5B0.9600
C2—C31.311 (4)C5—H5C0.9600
C2—H20.9300
C1—N1—H1A109.5C2—C3—C4124.2 (3)
C1—N1—H1B109.5C2—C3—C5121.0 (3)
H1A—N1—H1B109.5C4—C3—C5114.8 (3)
C1—N1—H1C109.5C3—C4—H4A109.5
H1A—N1—H1C109.5C3—C4—H4B109.5
H1B—N1—H1C109.5H4A—C4—H4B109.5
N1—C1—C2111.1 (2)C3—C4—H4C109.5
N1—C1—H1D109.4H4A—C4—H4C109.5
C2—C1—H1D109.4H4B—C4—H4C109.5
N1—C1—H1E109.4C3—C5—H5A109.5
C2—C1—H1E109.4C3—C5—H5B109.5
H1D—C1—H1E108.0H5A—C5—H5B109.5
C3—C2—C1126.7 (2)C3—C5—H5C109.5
C3—C2—H2116.6H5A—C5—H5C109.5
C1—C2—H2116.6H5B—C5—H5C109.5
N1—C1—C2—C3117.1 (3)C1—C2—C3—C5179.7 (3)
C1—C2—C3—C42.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.892.323.201 (2)173
N1—H1B···Cl1i0.892.363.2178 (16)163
N1—H1C···Cl1ii0.892.353.2173 (16)165
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2.
 

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