All interatomic distances of the title compound, C
5H
12N
+·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
CCDC reference: 170300
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
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
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+·Cl− | F(000) = 264 |
Mr = 121.61 | Dx = 1.102 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.1286 (12) Å | Cell parameters from 2025 reflections |
b = 5.8874 (7) Å | θ = 5–22° |
c = 8.8335 (9) Å | µ = 0.42 mm−1 |
β = 94.321 (8)° | T = 291 K |
V = 732.69 (13) Å3 | Plate, colourless |
Z = 4 | 0.44 × 0.25 × 0.04 mm |
Data collection top
Kuma KM4-CCD diffractometer | 1241 independent reflections |
Radiation source: fine-focus sealed tube | 1223 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 25.1°, θmin = 3.8° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −16→16 |
Tmin = 0.837, Tmax = 0.983 | k = −7→5 |
7034 measured reflections | l = −10→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.08877 (4) | 0.25531 (7) | 0.56750 (6) | 0.0435 (3) | |
N1 | −0.08159 (14) | 0.2554 (2) | 0.7868 (2) | 0.0433 (5) | |
H1A | −0.0306 | 0.2573 | 0.7333 | 0.065* | |
H1B | −0.0798 | 0.1327 | 0.8458 | 0.065* | |
H1C | −0.0821 | 0.3795 | 0.8442 | 0.065* | |
C1 | −0.16857 (19) | 0.2496 (3) | 0.6816 (3) | 0.0496 (6) | |
H1D | −0.1674 | 0.1156 | 0.6179 | 0.060* | |
H1E | −0.1699 | 0.3821 | 0.6162 | 0.060* | |
C2 | −0.25574 (19) | 0.2462 (3) | 0.7669 (3) | 0.0508 (6) | |
H2 | −0.2637 | 0.1208 | 0.8287 | 0.061* | |
C3 | −0.32232 (17) | 0.4016 (4) | 0.7638 (3) | 0.0621 (7) | |
C4 | −0.3200 (2) | 0.6189 (5) | 0.6750 (5) | 0.0925 (11) | |
H4A | −0.2612 | 0.6290 | 0.6277 | 0.139* | |
H4B | −0.3255 | 0.7456 | 0.7421 | 0.139* | |
H4C | −0.3720 | 0.6209 | 0.5984 | 0.139* | |
C5 | −0.4071 (2) | 0.3760 (8) | 0.8573 (5) | 0.1029 (12) | |
H5A | −0.4043 | 0.2312 | 0.9073 | 0.154* | |
H5B | −0.4644 | 0.3858 | 0.7921 | 0.154* | |
H5C | −0.4063 | 0.4948 | 0.9318 | 0.154* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0506 (4) | 0.0305 (4) | 0.0504 (4) | 0.00036 (17) | 0.0112 (3) | 0.00028 (17) |
N1 | 0.0484 (11) | 0.0327 (10) | 0.0503 (11) | 0.0011 (6) | 0.0146 (9) | −0.0007 (6) |
C1 | 0.0598 (15) | 0.0448 (14) | 0.0449 (13) | 0.0041 (8) | 0.0081 (11) | −0.0012 (8) |
C2 | 0.0487 (13) | 0.0428 (14) | 0.0607 (15) | −0.0058 (8) | 0.0028 (11) | 0.0030 (9) |
C3 | 0.0517 (13) | 0.0588 (15) | 0.0761 (17) | −0.0045 (11) | 0.0064 (12) | −0.0127 (12) |
C4 | 0.081 (2) | 0.0606 (18) | 0.137 (3) | 0.0132 (15) | 0.015 (2) | 0.0048 (18) |
C5 | 0.0607 (19) | 0.122 (3) | 0.130 (3) | −0.0042 (17) | 0.0281 (19) | 0.003 (2) |
Geometric parameters (Å, º) top
N1—C1 | 1.484 (3) | C3—C4 | 1.502 (4) |
N1—H1A | 0.8900 | C3—C5 | 1.513 (4) |
N1—H1B | 0.8900 | C4—H4A | 0.9600 |
N1—H1C | 0.8900 | C4—H4B | 0.9600 |
C1—C2 | 1.492 (4) | C4—H4C | 0.9600 |
C1—H1D | 0.9700 | C5—H5A | 0.9600 |
C1—H1E | 0.9700 | C5—H5B | 0.9600 |
C2—C3 | 1.311 (4) | C5—H5C | 0.9600 |
C2—H2 | 0.9300 | | |
| | | |
C1—N1—H1A | 109.5 | C2—C3—C4 | 124.2 (3) |
C1—N1—H1B | 109.5 | C2—C3—C5 | 121.0 (3) |
H1A—N1—H1B | 109.5 | C4—C3—C5 | 114.8 (3) |
C1—N1—H1C | 109.5 | C3—C4—H4A | 109.5 |
H1A—N1—H1C | 109.5 | C3—C4—H4B | 109.5 |
H1B—N1—H1C | 109.5 | H4A—C4—H4B | 109.5 |
N1—C1—C2 | 111.1 (2) | C3—C4—H4C | 109.5 |
N1—C1—H1D | 109.4 | H4A—C4—H4C | 109.5 |
C2—C1—H1D | 109.4 | H4B—C4—H4C | 109.5 |
N1—C1—H1E | 109.4 | C3—C5—H5A | 109.5 |
C2—C1—H1E | 109.4 | C3—C5—H5B | 109.5 |
H1D—C1—H1E | 108.0 | H5A—C5—H5B | 109.5 |
C3—C2—C1 | 126.7 (2) | C3—C5—H5C | 109.5 |
C3—C2—H2 | 116.6 | H5A—C5—H5C | 109.5 |
C1—C2—H2 | 116.6 | H5B—C5—H5C | 109.5 |
| | | |
N1—C1—C2—C3 | 117.1 (3) | C1—C2—C3—C5 | −179.7 (3) |
C1—C2—C3—C4 | −2.2 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1 | 0.89 | 2.32 | 3.201 (2) | 173 |
N1—H1B···Cl1i | 0.89 | 2.36 | 3.2178 (16) | 163 |
N1—H1C···Cl1ii | 0.89 | 2.35 | 3.2173 (16) | 165 |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2. |