Crystal structure of diiso-propyl-aminium di-chloro-acetate.

In the title compound, C6H16N(+)·C2HCl2O2 (-), the cation exhibits non-crystallographic C 2 symmetry. In the crystal, the components are linked by N-H⋯O and C-H⋯O hydrogen bonds into chains propagating along [010].

Related literature

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 ▸).

Experimental

Crystal data

C6H16N+·C2HCl2O2 −

M = 230.13

Monoclinic,

a = 10.0272 (2) Å

b = 9.04914 (17) Å

c = 13.6496 (3) Å

β = 106.433 (2)°

V = 1187.94 (4) Å3

Z = 4

Cu Kα radiation

μ = 4.71 mm−1

T = 120 K

0.36 × 0.28 × 0.24 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.662, T max = 1.000

11039 measured reflections

2107 independent reflections

1911 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.092

S = 1.03

2107 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.85 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015007586/gk2629sup1.cif

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007586/gk2629Isup2.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007586/gk2629fig1.tif

The mol­ecular structure of the title compound. The displacement parameters are shown at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015007586/gk2629fig2.tif

Crystal packing of the title compound, viewed down the b direction. Dashed lines indicate hydrogen bonds.

CCDC reference: 1060114

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO1i	0.92	1.87	2.788(2)	177
N1H1BO2ii	0.92	1.90	2.757(2)	154
C6H6O1iii	1.00	2.38	3.258(2)	146

Symmetry codes: (i) ; (ii) ; (iii) .