Cyclo­hexyl­ammonium dichloro­acetate

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.

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

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Computing details

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

Crystal data

C6H14N^+·C2HCl2O2^−	F(000) = 480
Mr = 228.10	Dx = 1.380 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5012 reflections
a = 6.6435 (8) Å	θ = 2.6–28.6°
b = 8.596 (1) Å	µ = 0.56 mm^−1
c = 19.135 (2) Å	T = 293 K
V = 1092.8 (2) Å^3	Block, colourless
Z = 4	0.36 × 0.18 × 0.16 mm

Data collection

CCD area detector diffractometer	2308 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
phi and ω scans	h = −8→8
9724 measured reflections	k = −11→11
2497 independent reflections	l = −23→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 0.2076P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2497 reflections	Δρmax = 0.28 e Å^−3
119 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.79188 (9)	0.84051 (6)	0.09568 (4)	0.06923 (18)
Cl2	0.40787 (7)	0.68190 (5)	0.10149 (3)	0.05118 (14)
O1	0.6319 (2)	0.43221 (14)	0.02881 (8)	0.0489 (3)
O2	0.9293 (2)	0.54366 (16)	0.04601 (10)	0.0623 (4)
N1	0.2368 (2)	0.32573 (16)	0.05461 (8)	0.0400 (3)
H1A	0.3514	0.3734	0.0436	0.060*
H1B	0.1346	0.3918	0.0497	0.060*
H1C	0.2186	0.2446	0.0264	0.060*
C1	0.7440 (3)	0.54286 (18)	0.04346 (9)	0.0361 (3)
C2	0.6372 (2)	0.70105 (18)	0.05455 (10)	0.0373 (3)
H2	0.6034	0.7418	0.0082	0.045*
C3	0.2462 (3)	0.2710 (2)	0.12862 (10)	0.0419 (4)
H3	0.2684	0.3613	0.1589	0.050*
C4	0.4200 (3)	0.1595 (3)	0.13795 (12)	0.0576 (5)
H4A	0.5452	0.2116	0.1264	0.069*
H4B	0.4040	0.0719	0.1065	0.069*
C5	0.4285 (4)	0.1012 (3)	0.21307 (14)	0.0737 (7)
H5A	0.5355	0.0251	0.2175	0.088*
H5B	0.4593	0.1875	0.2439	0.088*
C6	0.2320 (5)	0.0283 (3)	0.23508 (14)	0.0756 (7)
H6A	0.2104	−0.0663	0.2085	0.091*
H6B	0.2392	0.0005	0.2841	0.091*
C7	0.0571 (5)	0.1366 (4)	0.22380 (14)	0.0770 (8)
H7A	0.0690	0.2244	0.2554	0.092*
H7B	−0.0671	0.0825	0.2347	0.092*
C8	0.0481 (3)	0.1958 (3)	0.14873 (13)	0.0590 (5)
H8A	0.0200	0.1098	0.1174	0.071*
H8B	−0.0598	0.2711	0.1442	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0589 (3)	0.0484 (3)	0.1004 (4)	−0.0151 (2)	0.0005 (3)	−0.0276 (3)
Cl2	0.0435 (2)	0.0401 (2)	0.0699 (3)	0.00055 (19)	0.0143 (2)	−0.0091 (2)
O1	0.0407 (7)	0.0286 (6)	0.0773 (9)	−0.0040 (5)	0.0109 (6)	−0.0133 (6)
O2	0.0338 (7)	0.0378 (7)	0.1151 (13)	0.0066 (6)	−0.0001 (8)	0.0053 (8)
N1	0.0322 (7)	0.0276 (6)	0.0600 (8)	0.0001 (6)	−0.0024 (7)	−0.0054 (6)
C1	0.0351 (8)	0.0262 (7)	0.0470 (9)	0.0029 (7)	0.0030 (7)	0.0033 (6)
C2	0.0338 (8)	0.0268 (7)	0.0513 (9)	−0.0018 (6)	0.0008 (7)	−0.0039 (7)
C3	0.0398 (9)	0.0304 (8)	0.0554 (10)	−0.0028 (7)	−0.0002 (8)	−0.0084 (7)
C4	0.0439 (10)	0.0606 (13)	0.0684 (13)	0.0056 (10)	0.0020 (10)	0.0127 (10)
C5	0.0708 (16)	0.0781 (17)	0.0723 (15)	0.0058 (14)	−0.0059 (13)	0.0191 (13)
C6	0.098 (2)	0.0617 (14)	0.0668 (14)	−0.0034 (16)	0.0133 (15)	0.0121 (11)
C7	0.0717 (16)	0.0764 (17)	0.0828 (17)	−0.0062 (14)	0.0281 (14)	0.0054 (14)
C8	0.0411 (10)	0.0575 (13)	0.0784 (14)	−0.0041 (10)	0.0105 (10)	−0.0024 (12)

Geometric parameters (Å, º)

Cl1—C2	1.7641 (17)	C4—H4A	0.9700
Cl2—C2	1.7763 (17)	C4—H4B	0.9700
O1—C1	1.240 (2)	C5—C6	1.508 (4)
O2—C1	1.232 (2)	C5—H5A	0.9700
N1—C3	1.494 (2)	C5—H5B	0.9700
N1—H1A	0.8900	C6—C7	1.504 (4)
N1—H1B	0.8900	C6—H6A	0.9700
N1—H1C	0.8900	C6—H6B	0.9700
C1—C2	1.548 (2)	C7—C8	1.525 (4)
C2—H2	0.9800	C7—H7A	0.9700
C3—C4	1.511 (3)	C7—H7B	0.9700
C3—C8	1.516 (3)	C8—H8A	0.9700
C3—H3	0.9800	C8—H8B	0.9700
C4—C5	1.523 (3)
C3—N1—H1A	109.5	H4A—C4—H4B	108.1
C3—N1—H1B	109.5	C6—C5—C4	111.6 (2)
H1A—N1—H1B	109.5	C6—C5—H5A	109.3
C3—N1—H1C	109.5	C4—C5—H5A	109.3
H1A—N1—H1C	109.5	C6—C5—H5B	109.3
H1B—N1—H1C	109.5	C4—C5—H5B	109.3
O2—C1—O1	127.83 (16)	H5A—C5—H5B	108.0
O2—C1—C2	116.59 (15)	C7—C6—C5	111.8 (2)
O1—C1—C2	115.42 (15)	C7—C6—H6A	109.3
C1—C2—Cl1	113.02 (12)	C5—C6—H6A	109.3
C1—C2—Cl2	112.39 (11)	C7—C6—H6B	109.3
Cl1—C2—Cl2	109.70 (10)	C5—C6—H6B	109.3
C1—C2—H2	107.1	H6A—C6—H6B	107.9
Cl1—C2—H2	107.1	C6—C7—C8	111.8 (2)
Cl2—C2—H2	107.1	C6—C7—H7A	109.2
N1—C3—C4	110.13 (16)	C8—C7—H7A	109.2
N1—C3—C8	109.78 (16)	C6—C7—H7B	109.2
C4—C3—C8	111.28 (16)	C8—C7—H7B	109.2
N1—C3—H3	108.5	H7A—C7—H7B	107.9
C4—C3—H3	108.5	C3—C8—C7	110.3 (2)
C8—C3—H3	108.5	C3—C8—H8A	109.6
C3—C4—C5	110.38 (19)	C7—C8—H8A	109.6
C3—C4—H4A	109.6	C3—C8—H8B	109.6
C5—C4—H4A	109.6	C7—C8—H8B	109.6
C3—C4—H4B	109.6	H8A—C8—H8B	108.1
C5—C4—H4B	109.6
O2—C1—C2—Cl1	−19.0 (2)	C3—C4—C5—C6	55.5 (3)
O1—C1—C2—Cl1	165.27 (14)	C4—C5—C6—C7	−54.3 (3)
O2—C1—C2—Cl2	−143.78 (16)	C5—C6—C7—C8	54.0 (3)
O1—C1—C2—Cl2	40.4 (2)	N1—C3—C8—C7	178.94 (18)
N1—C3—C4—C5	−179.11 (18)	C4—C3—C8—C7	56.8 (3)
C8—C3—C4—C5	−57.1 (3)	C6—C7—C8—C3	−55.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1^i	0.89	1.94	2.8194 (19)	170
N1—H1B···O2^ii	0.89	1.89	2.7765 (19)	175
N1—H1A···Cl2	0.89	2.90	3.3868 (15)	116
N1—H1A···O1	0.89	1.95	2.8237 (19)	166

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x−1, y, z.