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By the reaction of diiso­propyl­amine (dip) with hydro­chloric acid and crystallization at room temperature, dipHCl, known from the literature, and the corresponding hemihydrate, C6H16N+·Cl-·0.5H2O or dipHCl·0.5H2O, have been obtained. By using a new humidity chamber for the powder diffraction study it has been proven that dipHCl reacts via a solid-solid phase transition to give dipHCl·0.5H2O on increasing the relative humidity of the sample atmosphere. The cations and anions are connected by hydrogen bonds to form chains along the crystallographic [100] direction. The extended polymeric zigzag chains form layers in the ac plane, separated by water mol­ecules. The cations and water molecules lie on crystallographic twofold rotation axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019347/cv6156sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019347/cv6156Isup2.hkl
Contains datablock I

CCDC reference: 200789

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.043
  • wR factor = 0.100
  • Data-to-parameter ratio = 15.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.168
Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 6.00 Perc.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: IPDS Software (Stoe & Cie, 1998); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(I) top
Crystal data top
C6H16N+·Cl·0.5H2ODx = 1.039 Mg m3
Mr = 146.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, CccaCell parameters from 5000 reflections
a = 10.289 (2) Åθ = 2.6–25.7°
b = 15.723 (3) ŵ = 0.34 mm1
c = 11.590 (2) ÅT = 293 K
V = 1874.9 (6) Å3Platelet, colourless
Z = 80.35 × 0.1 × 0.01 mm
F(000) = 648
Data collection top
Stoe IPDS
diffractometer
574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.168
Graphite monochromatorθmax = 25.0°, θmin = 4.2°
Detector resolution: 50 pixels mm-1h = 1212
ω scansk = 1818
11427 measured reflectionsl = 1313
819 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.01P)2 + 1.09P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
819 reflectionsΔρmax = 0.31 e Å3
54 parametersΔρmin = 0.26 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0035 (10)
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*/UeqOcc. (<1)
N10.25000.00000.6094 (2)0.0421 (6)
H10.1819 (15)0.0161 (14)0.6529 (17)0.052 (6)*
C10.1991 (2)0.07534 (14)0.5419 (2)0.0505 (6)
H1A0.12400.05680.49640.045 (6)*
Cl10.00000.06226 (5)0.75000.0599 (3)
O10.00000.25000.8704 (7)0.133 (3)0.50
H1O0.06650.23210.82600.199*0.50
C30.1545 (3)0.14214 (16)0.6275 (2)0.0652 (7)
H3A0.09230.11780.67960.081 (5)*
H3B0.22800.16260.67040.081 (5)*
H3C0.11510.18850.58660.081 (5)*
C20.3015 (3)0.10914 (18)0.4605 (2)0.0719 (8)
H2A0.32780.06490.40840.091 (5)*
H2B0.26640.15590.41730.091 (5)*
H2C0.37520.12810.50410.091 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0414 (13)0.0469 (14)0.0379 (15)0.0043 (11)0.0000.000
C10.0525 (12)0.0523 (12)0.0468 (15)0.0022 (10)0.0081 (10)0.0070 (10)
Cl10.0600 (5)0.0545 (5)0.0653 (6)0.0000.0189 (4)0.000
O10.226 (8)0.065 (4)0.108 (6)0.022 (5)0.0000.000
C30.0716 (16)0.0523 (15)0.0718 (19)0.0057 (11)0.0059 (13)0.0030 (12)
C20.0871 (18)0.0680 (16)0.0606 (19)0.0048 (14)0.0102 (14)0.0182 (14)
Geometric parameters (Å, º) top
N1—C11.513 (2)C3—H3A0.9600
N1—C1i1.513 (2)C3—H3B0.9600
C1—C21.510 (3)C3—H3C0.9600
C1—C31.516 (3)C2—H2A0.9601
C1—H1A0.9800C2—H2B0.9600
O1—H1O0.9009C2—H2C0.9600
C1—N1—C1i117.7 (3)H3A—C3—H3B109.5
C2—C1—N1110.93 (18)C1—C3—H3C109.3
C2—C1—C3112.1 (2)H3A—C3—H3C109.5
N1—C1—C3108.0 (2)H3B—C3—H3C109.5
C1—N1—H1103.9 (14)C1—C2—H2A109.6
C1i—N1—H1109.8 (15)C1—C2—H2B109.5
C2—C1—H1A108.6H2A—C2—H2B109.5
N1—C1—H1A108.6C1—C2—H2C109.4
C3—C1—H1A108.6H2A—C2—H2C109.5
C1—C3—H3A109.7H2B—C2—H2C109.5
C1—C3—H3B109.4
C1i—N1—C1—C256.61 (17)C1i—N1—C1—C3179.8 (2)
Symmetry code: (i) x+1/2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.90 (1)2.30 (1)3.1985 (14)175 (2)
O1—H1O···O1ii0.902.392.791 (16)107
Symmetry code: (ii) x, y, z+3/2.
 

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