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In the title compound, C6H12NO4+·Cl-, the cations and anions are joined together via strong hydrogen bonds, forming infinite chains running along the [100] direction. The cation has crystallographic mirror symmetry, and the anion also lies on a mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802022146/cf6227sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802022146/cf6227Isup2.hkl
Contains datablock I

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.163
  • Data-to-parameter ratio = 14.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Dimethyl iminiodiacetate chloride top
Crystal data top
C6H12NO4+·ClDx = 1.410 Mg m3
Mr = 197.62Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, PnmaCell parameters from 25 reflections
a = 7.0228 (4) Åθ = 21.1–32.1°
b = 17.298 (9) ŵ = 3.51 mm1
c = 7.6646 (5) ÅT = 293 K
V = 931.1 (5) Å3Needle, colourless
Z = 40.49 × 0.08 × 0.05 mm
F(000) = 416
Data collection top
Enraf-Nonius CAD-4
diffractometer
787 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 72.4°, θmin = 5.1°
ω–2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 2121
Tmin = 0.706, Tmax = 0.839l = 90
1837 measured reflections3 standard reflections every 180 min
950 independent reflections intensity decay: 4%
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) = 0.163 w = 1/[σ2(Fo2) + (0.0755P)2 + 0.752P]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max < 0.001
950 reflectionsΔρmax = 0.32 e Å3
64 parametersΔρmin = 0.72 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (8)
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
Cl0.18857 (14)0.25000.01795 (13)0.0511 (4)
O10.2949 (3)0.04572 (12)0.0195 (2)0.0507 (6)
O20.1140 (3)0.10952 (11)0.2134 (3)0.0554 (6)
N0.2310 (5)0.25000.0938 (4)0.0387 (7)
H10.252 (7)0.25000.205 (6)0.046*
H20.114 (7)0.25000.080 (6)0.046*
C10.3097 (4)0.17948 (17)0.0126 (3)0.0429 (7)
H1A0.28100.17940.11120.052*
H1B0.44710.17900.02600.052*
C20.2266 (4)0.10876 (15)0.0960 (3)0.0408 (7)
C30.2389 (5)0.02865 (19)0.0905 (4)0.0579 (9)
H3A0.11040.02570.13250.087*
H3B0.24700.06730.00090.087*
H3C0.32230.04220.18490.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0411 (6)0.0630 (7)0.0491 (6)0.0000.0021 (4)0.000
O10.0624 (13)0.0449 (11)0.0449 (11)0.0006 (10)0.0076 (9)0.0061 (8)
O20.0623 (14)0.0541 (12)0.0498 (12)0.0009 (10)0.0165 (10)0.0003 (9)
N0.0359 (16)0.0443 (17)0.0359 (16)0.0000.0027 (13)0.000
C10.0430 (15)0.0456 (16)0.0402 (14)0.0037 (12)0.0023 (11)0.0026 (11)
C20.0426 (14)0.0453 (15)0.0346 (13)0.0000 (12)0.0046 (11)0.0027 (10)
C30.071 (2)0.0479 (17)0.0550 (19)0.0018 (16)0.0024 (16)0.0006 (13)
Geometric parameters (Å, º) top
O1—C21.328 (3)C1—C21.499 (4)
O1—C31.451 (4)C1—H1A0.970
O2—C21.198 (3)C1—H1B0.970
N—C11.477 (3)C3—H3A0.960
N—H10.87 (5)C3—H3B0.960
N—H20.83 (5)C3—H3C0.960
C2—O1—C3117.7 (2)H1A—C1—H1B108.1
C1—N—C1i111.4 (3)O2—C2—O1125.4 (3)
C1—N—H1110.5 (15)O2—C2—C1124.6 (2)
C1—N—H2108.5 (16)O1—C2—C1110.0 (2)
H1—N—H2107 (5)O1—C3—H3A109.5
N—C1—C2110.4 (2)O1—C3—H3B109.5
N—C1—H1A109.6H3A—C3—H3B109.5
C2—C1—H1A109.6O1—C3—H3C109.5
N—C1—H1B109.6H3A—C3—H3C109.5
C2—C1—H1B109.6H3B—C3—H3C109.5
C1i—N—C1—C2179.51 (18)N—C1—C2—O20.9 (4)
C3—O1—C2—O24.3 (4)N—C1—C2—O1178.6 (2)
C3—O1—C2—C1176.3 (2)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1···Clii0.87 (5)2.43 (5)3.299 (3)180 (4)
N—H2···Cliii0.83 (5)2.25 (5)3.069 (3)168 (5)
Symmetry codes: (ii) x+1/2, y, z1/2; (iii) x, y, z.
 

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