Download citation
Download citation
link to html
The title compound, C7H17ClN+·Cl·H2O, is composed of discrete (chloro­methyl)triethyl­ammonium cations, Cl anions and water mol­ecules, which are held together by O—H...Cl hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021921/kj2014sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021921/kj2014IIsup2.hkl
Contains datablock II

CCDC reference: 614868

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.112
  • Data-to-parameter ratio = 27.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 13.34 su
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl7 - C7 .. 6.91 su PLAT482_ALERT_4_C Small D-H..A Angle Rep for C5 .. CL7 .. 99.60 Deg.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

(Chloromethyl)triethylammonium chloride monohydrate top
Crystal data top
C7H17ClN+·Cl·H2OF(000) = 440
Mr = 204.13Dx = 1.285 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 32948 reflections
a = 11.1642 (8) Åθ = 3.7–29.8°
b = 7.9798 (4) ŵ = 0.57 mm1
c = 12.3239 (9) ÅT = 100 K
β = 106.087 (6)°Block, colourless
V = 1054.92 (12) Å30.50 × 0.40 × 0.30 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
2977 independent reflections
Radiation source: fine-focus sealed tube2664 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 29.7°, θmin = 3.8°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1515
Tmin = 0.764, Tmax = 0.848k = 1111
26921 measured reflectionsl = 1617
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0699P)2 + 0.5992P]
where P = (Fo2 + 2Fc2)/3
2977 reflections(Δ/σ)max < 0.001
108 parametersΔρmax = 0.81 e Å3
2 restraintsΔρmin = 0.68 e Å3
Special details top

Experimental. ;

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
N10.49722 (11)0.55768 (15)0.25136 (10)0.0150 (2)
C10.50537 (13)0.45166 (18)0.15039 (12)0.0176 (3)
H1A0.43570.48330.08440.021*
H1B0.58400.47950.13210.021*
C20.50102 (14)0.2632 (2)0.16744 (14)0.0217 (3)
H2A0.50690.20550.09890.032*
H2B0.42240.23320.18320.032*
H2C0.57100.22950.23120.032*
C30.59489 (13)0.5068 (2)0.35936 (12)0.0185 (3)
H3A0.58140.57300.42290.022*
H3B0.58250.38730.37480.022*
C40.72871 (14)0.5313 (3)0.35578 (14)0.0274 (3)
H4A0.78570.49450.42750.041*
H4B0.74320.65010.34380.041*
H4C0.74360.46510.29380.041*
C50.51608 (16)0.74016 (19)0.22459 (14)0.0241 (3)
H5A0.59540.74960.20390.029*
H5B0.52480.80720.29400.029*
C60.41116 (16)0.81744 (18)0.12888 (13)0.0235 (3)
H6A0.43190.93410.11700.035*
H6B0.33260.81380.14970.035*
H6C0.40230.75360.05920.035*
C70.36992 (13)0.52783 (19)0.26842 (12)0.0177 (3)
H7A0.36500.41090.29370.021*
H7B0.30560.54240.19540.021*
Cl70.33800 (4)0.66575 (5)0.36889 (3)0.02545 (12)
O10.41162 (12)0.16234 (17)0.40115 (12)0.0305 (3)
H1C0.387 (2)0.113 (3)0.4504 (17)0.039 (7)*
H1D0.4819 (15)0.121 (4)0.411 (3)0.051 (8)*
Cl10.70328 (3)0.04516 (5)0.43291 (3)0.02070 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0156 (5)0.0158 (5)0.0128 (5)0.0021 (4)0.0026 (4)0.0009 (4)
C10.0179 (6)0.0214 (7)0.0135 (6)0.0016 (5)0.0044 (5)0.0013 (5)
C20.0214 (7)0.0203 (7)0.0252 (7)0.0012 (5)0.0098 (5)0.0034 (5)
C30.0156 (6)0.0241 (7)0.0138 (6)0.0014 (5)0.0005 (5)0.0018 (5)
C40.0162 (6)0.0437 (10)0.0212 (7)0.0053 (6)0.0031 (5)0.0022 (6)
C50.0319 (8)0.0170 (6)0.0214 (7)0.0075 (6)0.0039 (6)0.0024 (5)
C60.0325 (8)0.0127 (6)0.0181 (6)0.0053 (5)0.0053 (6)0.0021 (5)
C70.0153 (6)0.0210 (6)0.0169 (6)0.0008 (5)0.0047 (5)0.0011 (5)
Cl70.0257 (2)0.0285 (2)0.02206 (19)0.00523 (14)0.00640 (14)0.00147 (13)
O10.0198 (5)0.0333 (7)0.0371 (7)0.0018 (5)0.0059 (5)0.0173 (5)
Cl10.01760 (17)0.0268 (2)0.01816 (18)0.00233 (12)0.00572 (12)0.00070 (12)
Geometric parameters (Å, º) top
N1—C71.5120 (18)C4—H4B0.9800
N1—C51.5205 (19)C4—H4C0.9800
N1—C31.5235 (17)C5—C61.542 (2)
N1—C11.5281 (18)C5—H5A0.9900
C1—C21.521 (2)C5—H5B0.9900
C1—H1A0.9900C6—H6A0.9800
C1—H1B0.9900C6—H6B0.9800
C2—H2A0.9800C6—H6C0.9800
C2—H2B0.9800C7—Cl71.7653 (15)
C2—H2C0.9800C7—H7A0.9900
C3—C41.520 (2)C7—H7B0.9900
C3—H3A0.9900O1—H1C0.832 (10)
C3—H3B0.9900O1—H1D0.829 (10)
C4—H4A0.9800
C7—N1—C5111.90 (12)C3—C4—H4B109.5
C7—N1—C3108.02 (11)H4A—C4—H4B109.5
C5—N1—C3109.64 (11)C3—C4—H4C109.5
C7—N1—C1107.24 (10)H4A—C4—H4C109.5
C5—N1—C1108.09 (11)H4B—C4—H4C109.5
C3—N1—C1111.98 (11)N1—C5—C6115.30 (12)
C2—C1—N1115.05 (12)N1—C5—H5A108.4
C2—C1—H1A108.5C6—C5—H5A108.4
N1—C1—H1A108.5N1—C5—H5B108.4
C2—C1—H1B108.5C6—C5—H5B108.4
N1—C1—H1B108.5H5A—C5—H5B107.5
H1A—C1—H1B107.5C5—C6—H6A109.5
C1—C2—H2A109.5C5—C6—H6B109.5
C1—C2—H2B109.5H6A—C6—H6B109.5
H2A—C2—H2B109.5C5—C6—H6C109.5
C1—C2—H2C109.5H6A—C6—H6C109.5
H2A—C2—H2C109.5H6B—C6—H6C109.5
H2B—C2—H2C109.5N1—C7—Cl7112.31 (10)
C4—C3—N1114.32 (12)N1—C7—H7A109.1
C4—C3—H3A108.7Cl7—C7—H7A109.1
N1—C3—H3A108.7N1—C7—H7B109.1
C4—C3—H3B108.7Cl7—C7—H7B109.1
N1—C3—H3B108.7H7A—C7—H7B107.9
H3A—C3—H3B107.6H1C—O1—H1D102 (3)
C3—C4—H4A109.5
C7—N1—C1—C264.85 (15)C7—N1—C5—C650.45 (18)
C5—N1—C1—C2174.33 (12)C3—N1—C5—C6170.28 (14)
C3—N1—C1—C253.47 (16)C1—N1—C5—C667.41 (17)
C7—N1—C3—C4179.43 (13)C5—N1—C7—Cl752.76 (14)
C5—N1—C3—C457.26 (17)C3—N1—C7—Cl768.01 (13)
C1—N1—C3—C462.71 (16)C1—N1—C7—Cl7171.13 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1D···Cl10.83 (1)2.49 (1)3.3051 (13)170 (3)
O1—H1C···Cl1i0.83 (1)2.34 (1)3.1660 (13)172 (3)
C7—H7A···O10.992.363.3131 (19)161
C7—H7B···O1ii0.992.573.429 (2)145
C1—H1A···Cl1iii0.992.753.6809 (15)156
C1—H1B···Cl1iv0.992.763.7471 (15)176
C3—H3A···Cl70.992.723.1677 (15)108
C5—H5B···Cl70.992.753.0704 (18)100
Symmetry codes: (i) x+1, y, z+1; (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z1/2; (iv) x+3/2, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds