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The title compound, C6H14N+·C2HCl2O2-, (I), was obtained as a byproduct of the oxidation of the chiral compound 5-(R)-menth­yloxybutyrolacto[3,4-b]-2(S)-6(R)-1-N-cyclo­hexyl­azir­idine. The structure determination of (I) shows that the cations and anions are connected through weak inter­molecular hydrogen bonding, forming a complicated network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035324/hg6248sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035324/hg6248Isup2.hkl
Contains datablock I

CCDC reference: 293907

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](Wave) = 0.000 Å
  • R factor = 0.030
  • wR factor = 0.078
  • Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 2497 Count of symmetry unique reflns 1477 Completeness (_total/calc) 169.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1020 Fraction of Friedel pairs measured 0.691 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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: APEXII (Bruker 2004); cell refinement: APEXII; data reduction: SAINT (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.

Cyclohexylammonium dichloroacetate top
Crystal data top
C6H14N+·C2HCl2O2F(000) = 480
Mr = 228.10Dx = 1.380 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5012 reflections
a = 6.6435 (8) Åθ = 2.6–28.6°
b = 8.596 (1) ŵ = 0.56 mm1
c = 19.135 (2) ÅT = 293 K
V = 1092.8 (2) Å3Block, colourless
Z = 40.36 × 0.18 × 0.16 mm
Data collection top
CCD area detector
diffractometer
2308 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
phi and ω scansh = 88
9724 measured reflectionsk = 1111
2497 independent reflectionsl = 2324
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0362P)2 + 0.2076P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2497 reflectionsΔρmax = 0.28 e Å3
119 parametersΔρmin = 0.30 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (7)
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
Cl10.79188 (9)0.84051 (6)0.09568 (4)0.06923 (18)
Cl20.40787 (7)0.68190 (5)0.10149 (3)0.05118 (14)
O10.6319 (2)0.43221 (14)0.02881 (8)0.0489 (3)
O20.9293 (2)0.54366 (16)0.04601 (10)0.0623 (4)
N10.2368 (2)0.32573 (16)0.05461 (8)0.0400 (3)
H1A0.35140.37340.04360.060*
H1B0.13460.39180.04970.060*
H1C0.21860.24460.02640.060*
C10.7440 (3)0.54286 (18)0.04346 (9)0.0361 (3)
C20.6372 (2)0.70105 (18)0.05455 (10)0.0373 (3)
H20.60340.74180.00820.045*
C30.2462 (3)0.2710 (2)0.12862 (10)0.0419 (4)
H30.26840.36130.15890.050*
C40.4200 (3)0.1595 (3)0.13795 (12)0.0576 (5)
H4A0.54520.21160.12640.069*
H4B0.40400.07190.10650.069*
C50.4285 (4)0.1012 (3)0.21307 (14)0.0737 (7)
H5A0.53550.02510.21750.088*
H5B0.45930.18750.24390.088*
C60.2320 (5)0.0283 (3)0.23508 (14)0.0756 (7)
H6A0.21040.06630.20850.091*
H6B0.23920.00050.28410.091*
C70.0571 (5)0.1366 (4)0.22380 (14)0.0770 (8)
H7A0.06900.22440.25540.092*
H7B0.06710.08250.23470.092*
C80.0481 (3)0.1958 (3)0.14873 (13)0.0590 (5)
H8A0.02000.10980.11740.071*
H8B0.05980.27110.14420.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0589 (3)0.0484 (3)0.1004 (4)0.0151 (2)0.0005 (3)0.0276 (3)
Cl20.0435 (2)0.0401 (2)0.0699 (3)0.00055 (19)0.0143 (2)0.0091 (2)
O10.0407 (7)0.0286 (6)0.0773 (9)0.0040 (5)0.0109 (6)0.0133 (6)
O20.0338 (7)0.0378 (7)0.1151 (13)0.0066 (6)0.0001 (8)0.0053 (8)
N10.0322 (7)0.0276 (6)0.0600 (8)0.0001 (6)0.0024 (7)0.0054 (6)
C10.0351 (8)0.0262 (7)0.0470 (9)0.0029 (7)0.0030 (7)0.0033 (6)
C20.0338 (8)0.0268 (7)0.0513 (9)0.0018 (6)0.0008 (7)0.0039 (7)
C30.0398 (9)0.0304 (8)0.0554 (10)0.0028 (7)0.0002 (8)0.0084 (7)
C40.0439 (10)0.0606 (13)0.0684 (13)0.0056 (10)0.0020 (10)0.0127 (10)
C50.0708 (16)0.0781 (17)0.0723 (15)0.0058 (14)0.0059 (13)0.0191 (13)
C60.098 (2)0.0617 (14)0.0668 (14)0.0034 (16)0.0133 (15)0.0121 (11)
C70.0717 (16)0.0764 (17)0.0828 (17)0.0062 (14)0.0281 (14)0.0054 (14)
C80.0411 (10)0.0575 (13)0.0784 (14)0.0041 (10)0.0105 (10)0.0024 (12)
Geometric parameters (Å, º) top
Cl1—C21.7641 (17)C4—H4A0.9700
Cl2—C21.7763 (17)C4—H4B0.9700
O1—C11.240 (2)C5—C61.508 (4)
O2—C11.232 (2)C5—H5A0.9700
N1—C31.494 (2)C5—H5B0.9700
N1—H1A0.8900C6—C71.504 (4)
N1—H1B0.8900C6—H6A0.9700
N1—H1C0.8900C6—H6B0.9700
C1—C21.548 (2)C7—C81.525 (4)
C2—H20.9800C7—H7A0.9700
C3—C41.511 (3)C7—H7B0.9700
C3—C81.516 (3)C8—H8A0.9700
C3—H30.9800C8—H8B0.9700
C4—C51.523 (3)
C3—N1—H1A109.5H4A—C4—H4B108.1
C3—N1—H1B109.5C6—C5—C4111.6 (2)
H1A—N1—H1B109.5C6—C5—H5A109.3
C3—N1—H1C109.5C4—C5—H5A109.3
H1A—N1—H1C109.5C6—C5—H5B109.3
H1B—N1—H1C109.5C4—C5—H5B109.3
O2—C1—O1127.83 (16)H5A—C5—H5B108.0
O2—C1—C2116.59 (15)C7—C6—C5111.8 (2)
O1—C1—C2115.42 (15)C7—C6—H6A109.3
C1—C2—Cl1113.02 (12)C5—C6—H6A109.3
C1—C2—Cl2112.39 (11)C7—C6—H6B109.3
Cl1—C2—Cl2109.70 (10)C5—C6—H6B109.3
C1—C2—H2107.1H6A—C6—H6B107.9
Cl1—C2—H2107.1C6—C7—C8111.8 (2)
Cl2—C2—H2107.1C6—C7—H7A109.2
N1—C3—C4110.13 (16)C8—C7—H7A109.2
N1—C3—C8109.78 (16)C6—C7—H7B109.2
C4—C3—C8111.28 (16)C8—C7—H7B109.2
N1—C3—H3108.5H7A—C7—H7B107.9
C4—C3—H3108.5C3—C8—C7110.3 (2)
C8—C3—H3108.5C3—C8—H8A109.6
C3—C4—C5110.38 (19)C7—C8—H8A109.6
C3—C4—H4A109.6C3—C8—H8B109.6
C5—C4—H4A109.6C7—C8—H8B109.6
C3—C4—H4B109.6H8A—C8—H8B108.1
C5—C4—H4B109.6
O2—C1—C2—Cl119.0 (2)C3—C4—C5—C655.5 (3)
O1—C1—C2—Cl1165.27 (14)C4—C5—C6—C754.3 (3)
O2—C1—C2—Cl2143.78 (16)C5—C6—C7—C854.0 (3)
O1—C1—C2—Cl240.4 (2)N1—C3—C8—C7178.94 (18)
N1—C3—C4—C5179.11 (18)C4—C3—C8—C756.8 (3)
C8—C3—C4—C557.1 (3)C6—C7—C8—C355.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.891.942.8194 (19)170
N1—H1B···O2ii0.891.892.7765 (19)175
N1—H1A···Cl20.892.903.3868 (15)116
N1—H1A···O10.891.952.8237 (19)166
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x1, y, z.
 

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