



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015007586/gk2629sup1.cif |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015007586/gk2629Isup2.cml |
CCDC reference: 1060114
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.092
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.5 Note
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
Single crystals suitable for X-ray analysis were obtained by slow solvent evaporation from a solution of the title compound in a dichloromethane/cyclohexane mixture (1:1 v/v) at room temperature.
All H atoms were positioned geometrically and constrained to ride on the parent atoms, with N—H = 0.92 Å and C—H = 0.98–1.00 Å, and with Uiso(H) = 1.5Ueq(methyl C) or 1.2Ueq(C, N) for other H atoms.
Diisopropylaminium dichlorocacetate (DADA) is the effective constituent of Vitamin B15 (Gelernt et al., 2009). Recently, DADA has been found as a potential PDK4 inhibitor for treatment of severe influenza (Yamane et al., 2014). Moreover the desirable therapeutic effects of colorectal cancer in mat is shown (Liu et al., 2015). No data about the crystal structure of diisopropylaminium dichlorocacetate has been reported so far.
The title molecule is shown in Fig. 1. The asymmetric unit contains one diisopropylaminium cation and one dichloroacetate anion. In the crystal structure, the cations and anions are linked by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig.2) to form chains propagating along [010].
For the background to the biological activity of the title compound, see: Gelernt & Herbert (2009); Yamane et al. (2014); Liu et al. (2015). For a related structure, see: Yu & Qian (2009).
Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C6H16N+·C2HCl2O2− | F(000) = 488 |
Mr = 230.13 | Dx = 1.287 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 10.0272 (2) Å | Cell parameters from 5039 reflections |
b = 9.04914 (17) Å | θ = 4.6–66.9° |
c = 13.6496 (3) Å | µ = 4.71 mm−1 |
β = 106.433 (2)° | T = 120 K |
V = 1187.94 (4) Å3 | Block, colourless |
Z = 4 | 0.36 × 0.28 × 0.24 mm |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 2107 independent reflections |
Radiation source: sealed X-ray tube, Enhance Ultra (Cu) X-ray Source | 1911 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.026 |
Detector resolution: 10.4674 pixels mm-1 | θmax = 66.9°, θmin = 4.6° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −7→10 |
Tmin = 0.662, Tmax = 1.000 | l = −16→16 |
11039 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0344P)2 + 1.3398P] where P = (Fo2 + 2Fc2)/3 |
2107 reflections | (Δ/σ)max < 0.001 |
122 parameters | Δρmax = 0.81 e Å−3 |
0 restraints | Δρmin = −0.85 e Å−3 |
C6H16N+·C2HCl2O2− | V = 1187.94 (4) Å3 |
Mr = 230.13 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 10.0272 (2) Å | µ = 4.71 mm−1 |
b = 9.04914 (17) Å | T = 120 K |
c = 13.6496 (3) Å | 0.36 × 0.28 × 0.24 mm |
β = 106.433 (2)° |
Agilent Xcalibur Atlas Gemini ultra diffractometer | 2107 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 1911 reflections with I > 2σ(I) |
Tmin = 0.662, Tmax = 1.000 | Rint = 0.026 |
11039 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.81 e Å−3 |
2107 reflections | Δρmin = −0.85 e Å−3 |
122 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat with a nominal stability of 0.1 K. . |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.53986 (5) | 0.16195 (6) | 0.60806 (5) | 0.04006 (18) | |
Cl2 | 0.62278 (7) | −0.05527 (9) | 0.76920 (6) | 0.0651 (3) | |
O1 | 0.86608 (14) | −0.08510 (15) | 0.66082 (12) | 0.0292 (3) | |
O2 | 0.84614 (15) | 0.15792 (15) | 0.68081 (12) | 0.0308 (3) | |
N1 | 0.15036 (16) | −0.05351 (17) | 0.75375 (12) | 0.0202 (3) | |
H1A | 0.0563 | −0.0607 | 0.7230 | 0.024* | |
H1B | 0.1801 | −0.1441 | 0.7822 | 0.024* | |
C2 | 0.80092 (19) | 0.0312 (2) | 0.66498 (14) | 0.0216 (4) | |
C3 | 0.2208 (2) | −0.0234 (2) | 0.67193 (15) | 0.0268 (4) | |
H3 | 0.3218 | −0.0050 | 0.7050 | 0.032* | |
C6 | 0.1729 (2) | 0.0574 (2) | 0.83878 (15) | 0.0256 (4) | |
H6 | 0.1401 | 0.1563 | 0.8087 | 0.031* | |
C4 | 0.1577 (2) | 0.1123 (3) | 0.61147 (17) | 0.0331 (5) | |
H4A | 0.0568 | 0.0998 | 0.5855 | 0.050* | |
H4B | 0.1972 | 0.1253 | 0.5540 | 0.050* | |
H4C | 0.1785 | 0.1995 | 0.6558 | 0.050* | |
C1 | 0.6441 (2) | 0.0036 (2) | 0.65013 (17) | 0.0291 (5) | |
H1 | 0.6122 | −0.0772 | 0.5989 | 0.035* | |
C7 | 0.0847 (3) | 0.0110 (3) | 0.90727 (17) | 0.0362 (5) | |
H7A | −0.0130 | 0.0049 | 0.8669 | 0.054* | |
H7B | 0.0943 | 0.0840 | 0.9619 | 0.054* | |
H7C | 0.1158 | −0.0858 | 0.9373 | 0.054* | |
C5 | 0.2054 (3) | −0.1610 (3) | 0.60590 (18) | 0.0421 (6) | |
H5A | 0.2486 | −0.2451 | 0.6483 | 0.063* | |
H5B | 0.2513 | −0.1450 | 0.5522 | 0.063* | |
H5C | 0.1065 | −0.1815 | 0.5747 | 0.063* | |
C8 | 0.3249 (2) | 0.0689 (3) | 0.8971 (2) | 0.0436 (6) | |
H8A | 0.3593 | −0.0283 | 0.9247 | 0.065* | |
H8B | 0.3363 | 0.1395 | 0.9533 | 0.065* | |
H8C | 0.3779 | 0.1029 | 0.8511 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0265 (3) | 0.0351 (3) | 0.0558 (4) | 0.0130 (2) | 0.0072 (2) | 0.0078 (2) |
Cl2 | 0.0341 (3) | 0.0849 (5) | 0.0860 (5) | 0.0143 (3) | 0.0328 (3) | 0.0510 (4) |
O1 | 0.0201 (7) | 0.0203 (7) | 0.0470 (9) | 0.0020 (6) | 0.0090 (6) | −0.0021 (6) |
O2 | 0.0266 (7) | 0.0206 (7) | 0.0473 (9) | −0.0036 (6) | 0.0139 (6) | −0.0056 (6) |
N1 | 0.0162 (7) | 0.0192 (8) | 0.0250 (8) | 0.0001 (6) | 0.0055 (6) | 0.0007 (6) |
C2 | 0.0188 (9) | 0.0231 (10) | 0.0229 (9) | 0.0003 (8) | 0.0056 (7) | 0.0012 (7) |
C3 | 0.0173 (9) | 0.0376 (12) | 0.0271 (10) | −0.0007 (8) | 0.0091 (8) | 0.0046 (9) |
C6 | 0.0270 (10) | 0.0204 (10) | 0.0292 (10) | 0.0020 (8) | 0.0078 (8) | −0.0026 (8) |
C4 | 0.0333 (12) | 0.0334 (12) | 0.0334 (11) | −0.0038 (9) | 0.0106 (9) | 0.0076 (9) |
C1 | 0.0187 (10) | 0.0231 (10) | 0.0434 (12) | 0.0032 (8) | 0.0053 (9) | 0.0030 (9) |
C7 | 0.0416 (13) | 0.0394 (13) | 0.0313 (11) | 0.0023 (10) | 0.0161 (10) | −0.0025 (10) |
C5 | 0.0558 (15) | 0.0426 (14) | 0.0327 (12) | 0.0147 (12) | 0.0201 (11) | 0.0021 (10) |
C8 | 0.0314 (12) | 0.0473 (14) | 0.0466 (14) | −0.0040 (11) | 0.0020 (10) | −0.0203 (12) |
Cl1—C1 | 1.771 (2) | C6—C8 | 1.511 (3) |
Cl2—C1 | 1.780 (2) | C4—H4A | 0.9800 |
O1—C2 | 1.248 (2) | C4—H4B | 0.9800 |
O2—C2 | 1.230 (2) | C4—H4C | 0.9800 |
N1—H1A | 0.9200 | C1—H1 | 1.0000 |
N1—H1B | 0.9200 | C7—H7A | 0.9800 |
N1—C3 | 1.505 (2) | C7—H7B | 0.9800 |
N1—C6 | 1.503 (2) | C7—H7C | 0.9800 |
C2—C1 | 1.548 (3) | C5—H5A | 0.9800 |
C3—H3 | 1.0000 | C5—H5B | 0.9800 |
C3—C4 | 1.514 (3) | C5—H5C | 0.9800 |
C3—C5 | 1.519 (3) | C8—H8A | 0.9800 |
C6—H6 | 1.0000 | C8—H8B | 0.9800 |
C6—C7 | 1.516 (3) | C8—H8C | 0.9800 |
H1A—N1—H1B | 107.3 | H4B—C4—H4C | 109.5 |
C3—N1—H1A | 108.1 | Cl1—C1—Cl2 | 109.02 (12) |
C3—N1—H1B | 108.1 | Cl1—C1—H1 | 108.8 |
C6—N1—H1A | 108.1 | Cl2—C1—H1 | 108.8 |
C6—N1—H1B | 108.1 | C2—C1—Cl1 | 113.38 (14) |
C6—N1—C3 | 116.92 (15) | C2—C1—Cl2 | 107.99 (14) |
O1—C2—C1 | 112.56 (16) | C2—C1—H1 | 108.8 |
O2—C2—O1 | 128.50 (18) | C6—C7—H7A | 109.5 |
O2—C2—C1 | 118.92 (17) | C6—C7—H7B | 109.5 |
N1—C3—H3 | 108.9 | C6—C7—H7C | 109.5 |
N1—C3—C4 | 109.89 (16) | H7A—C7—H7B | 109.5 |
N1—C3—C5 | 107.58 (17) | H7A—C7—H7C | 109.5 |
C4—C3—H3 | 108.9 | H7B—C7—H7C | 109.5 |
C4—C3—C5 | 112.62 (18) | C3—C5—H5A | 109.5 |
C5—C3—H3 | 108.9 | C3—C5—H5B | 109.5 |
N1—C6—H6 | 108.7 | C3—C5—H5C | 109.5 |
N1—C6—C7 | 107.75 (16) | H5A—C5—H5B | 109.5 |
N1—C6—C8 | 111.19 (16) | H5A—C5—H5C | 109.5 |
C7—C6—H6 | 108.7 | H5B—C5—H5C | 109.5 |
C8—C6—H6 | 108.7 | C6—C8—H8A | 109.5 |
C8—C6—C7 | 111.81 (19) | C6—C8—H8B | 109.5 |
C3—C4—H4A | 109.5 | C6—C8—H8C | 109.5 |
C3—C4—H4B | 109.5 | H8A—C8—H8B | 109.5 |
C3—C4—H4C | 109.5 | H8A—C8—H8C | 109.5 |
H4A—C4—H4B | 109.5 | H8B—C8—H8C | 109.5 |
H4A—C4—H4C | 109.5 | ||
O1—C2—C1—Cl1 | −157.58 (15) | C3—N1—C6—C7 | 175.93 (16) |
O1—C2—C1—Cl2 | 81.51 (19) | C3—N1—C6—C8 | −61.2 (2) |
O2—C2—C1—Cl1 | 23.8 (2) | C6—N1—C3—C4 | −67.1 (2) |
O2—C2—C1—Cl2 | −97.11 (19) | C6—N1—C3—C5 | 169.99 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.92 | 1.87 | 2.788 (2) | 177 |
N1—H1B···O2ii | 0.92 | 1.90 | 2.757 (2) | 154 |
C6—H6···O1iii | 1.00 | 2.38 | 3.258 (2) | 146 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.92 | 1.87 | 2.788 (2) | 177.3 |
N1—H1B···O2ii | 0.92 | 1.90 | 2.757 (2) | 154.2 |
C6—H6···O1iii | 1.00 | 2.38 | 3.258 (2) | 146.0 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2. |
Diisopropylaminium dichlorocacetate (DADA) is the effective constituent of Vitamin B15 (Gelernt et al., 2009). Recently, DADA has been found as a potential PDK4 inhibitor for treatment of severe influenza (Yamane et al., 2014). Moreover the desirable therapeutic effects of colorectal cancer in mat is shown (Liu et al., 2015). No data about the crystal structure of diisopropylaminium dichlorocacetate has been reported so far.
The title molecule is shown in Fig. 1. The asymmetric unit contains one diisopropylaminium cation and one dichloroacetate anion. In the crystal structure, the cations and anions are linked by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1, Fig.2) to form chains propagating along [010].