1,3-Dihydr-oxy-2-(hydroxy-meth-yl)propan-2-aminium 2,2-dichloro-acetate.

The title compound, C(4)H(12)NO(3) (+)·C(2)HCl(2)O(2) (-), was obtained from dichloro-acetic acid and 2-amino-2-(hydroxy-meth-yl)propane-1,3-diol. In the crystal structure, the cations and anions are connected by inter-molecular N-H⋯O and O-H⋯O hydrogen bonding, forming a two-dimensional array parallel to (001). The crystal used for analysis was a merohedral twin, as indicated by the Flack parameter of 0.67 (6).

Related literature

For the engineering of organic crystals for quadratic non-linear optics, see: Etter & Frankenbach (1989 ▶); Yaghi et al. (1997 ▶). For hydrogen-bond networks, see: Etter (1990 ▶).

Experimental

Crystal data

C4H12NO3 +·C2HCl2O2 −

M = 250.07

Monoclinic,

a = 8.6231 (17) Å

b = 6.1376 (12) Å

c = 9.898 (2) Å

β = 97.03 (3)°

V = 519.92 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.62 mm−1

T = 293 K

0.22 × 0.18 × 0.12 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.875, T max = 0.929

4914 measured reflections

2044 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.069

S = 1.10

2044 reflections

130 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 920 Friedel pairs

Flack parameter: 0.67 (6)

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016626/dn2442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016626/dn2442Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H12NO3+·C2HCl2O2−	F(000) = 260
Mr = 250.07	Dx = 1.597 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 735 reflections
a = 8.6231 (17) Å	θ = 2.8–27.5°
b = 6.1376 (12) Å	µ = 0.62 mm−1
c = 9.898 (2) Å	T = 293 K
β = 97.03 (3)°	Prism, colourless
V = 519.92 (18) Å3	0.22 × 0.18 × 0.12 mm
Z = 2

Rigaku SCXmini diffractometer	2044 independent reflections
Radiation source: fine-focus sealed tube	1951 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.875, Tmax = 0.929	l = −12→12
4914 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0218P)2 + 0.166P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2044 reflections	Δρmax = 0.23 e Å−3
130 parameters	Δρmin = −0.25 e Å−3
3 restraints	Absolute structure: Flack (1983), 920 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.67 (6)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.86491 (9)	0.39154 (15)	0.00483 (7)	0.0630 (2)
Cl2	0.70850 (10)	0.03942 (11)	0.13016 (8)	0.0598 (2)
C1	0.6938 (3)	0.3135 (4)	0.0737 (2)	0.0342 (5)
H1	0.6046	0.3263	0.0026	0.041*
C2	0.6675 (2)	0.4656 (4)	0.1919 (2)	0.0282 (5)
C3	0.2265 (2)	0.2569 (3)	0.3756 (2)	0.0215 (4)
C4	0.3748 (2)	0.1471 (3)	0.3394 (2)	0.0248 (4)
H4A	0.3540	0.0827	0.2496	0.030*
H4B	0.4558	0.2562	0.3365	0.030*
C5	0.0883 (2)	0.0986 (3)	0.3577 (2)	0.0249 (4)
H5A	0.0543	0.0801	0.2613	0.030*
H5B	0.1226	−0.0423	0.3944	0.030*
C6	0.1911 (2)	0.4607 (3)	0.2892 (2)	0.0270 (4)
H6A	0.1841	0.4215	0.1937	0.032*
H6B	0.0905	0.5188	0.3058	0.032*
N1	0.25465 (19)	0.3243 (3)	0.52217 (16)	0.0221 (3)
H1A	0.3470	0.3903	0.5382	0.033*
H1B	0.2540	0.2070	0.5750	0.033*
H1C	0.1797	0.4156	0.5403	0.033*
O1	0.54454 (19)	0.5709 (3)	0.17435 (18)	0.0444 (4)
O2	0.76863 (19)	0.4708 (3)	0.29336 (16)	0.0403 (4)
O3	0.42905 (16)	−0.0160 (2)	0.43407 (15)	0.0306 (4)
H3	0.3857	−0.1281	0.4071	0.046*
O4	0.30642 (17)	0.6233 (2)	0.31776 (17)	0.0336 (4)
H4	0.3805	0.5959	0.2759	0.050*
O5	−0.04042 (15)	0.1704 (3)	0.42311 (15)	0.0274 (3)
H5	−0.0931	0.2564	0.3735	0.041*

	U11	U22	U33	U12	U13	U23
Cl1	0.0535 (4)	0.0984 (7)	0.0405 (4)	−0.0075 (4)	0.0196 (3)	−0.0042 (4)
Cl2	0.0872 (5)	0.0321 (3)	0.0549 (4)	−0.0001 (4)	−0.0123 (4)	−0.0081 (3)
C1	0.0339 (12)	0.0377 (13)	0.0292 (11)	0.0008 (10)	−0.0040 (9)	−0.0007 (10)
C2	0.0274 (11)	0.0271 (10)	0.0304 (11)	−0.0002 (10)	0.0048 (9)	0.0064 (9)
C3	0.0185 (9)	0.0225 (10)	0.0233 (10)	−0.0014 (8)	0.0018 (8)	0.0011 (8)
C4	0.0213 (10)	0.0248 (11)	0.0288 (11)	0.0005 (9)	0.0052 (9)	0.0000 (9)
C5	0.0191 (9)	0.0233 (11)	0.0324 (11)	−0.0007 (8)	0.0029 (8)	−0.0030 (9)
C6	0.0247 (10)	0.0227 (10)	0.0332 (11)	0.0007 (9)	0.0017 (9)	0.0044 (9)
N1	0.0180 (7)	0.0224 (8)	0.0259 (9)	0.0000 (7)	0.0031 (7)	−0.0006 (7)
O1	0.0347 (9)	0.0503 (11)	0.0494 (10)	0.0142 (8)	0.0097 (8)	0.0129 (9)
O2	0.0424 (9)	0.0425 (10)	0.0337 (9)	0.0120 (8)	−0.0048 (7)	−0.0105 (7)
O3	0.0238 (7)	0.0236 (8)	0.0433 (9)	0.0036 (6)	−0.0002 (7)	0.0001 (7)
O4	0.0293 (8)	0.0219 (7)	0.0510 (10)	−0.0038 (6)	0.0105 (7)	0.0024 (7)
O5	0.0179 (7)	0.0308 (8)	0.0337 (8)	−0.0002 (6)	0.0043 (6)	0.0027 (6)

Cl1—C1	1.765 (2)	C5—O5	1.421 (2)
Cl2—C1	1.773 (3)	C5—H5A	0.9700
C1—C2	1.536 (3)	C5—H5B	0.9700
C1—H1	0.9800	C6—O4	1.413 (3)
C2—O1	1.236 (3)	C6—H6A	0.9700
C2—O2	1.247 (3)	C6—H6B	0.9700
C3—N1	1.499 (3)	N1—H1A	0.8900
C3—C6	1.525 (3)	N1—H1B	0.8900
C3—C4	1.527 (3)	N1—H1C	0.8900
C3—C5	1.531 (3)	O3—H3	0.8119
C4—O3	1.411 (2)	O4—H4	0.8205
C4—H4A	0.9700	O5—H5	0.8200
C4—H4B	0.9700
C2—C1—Cl1	109.75 (16)	O5—C5—C3	112.99 (16)
C2—C1—Cl2	110.36 (16)	O5—C5—H5A	109.0
Cl1—C1—Cl2	110.39 (14)	C3—C5—H5A	109.0
C2—C1—H1	108.8	O5—C5—H5B	109.0
Cl1—C1—H1	108.8	C3—C5—H5B	109.0
Cl2—C1—H1	108.8	H5A—C5—H5B	107.8
O1—C2—O2	127.1 (2)	O4—C6—C3	112.27 (17)
O1—C2—C1	114.5 (2)	O4—C6—H6A	109.2
O2—C2—C1	118.38 (19)	C3—C6—H6A	109.2
N1—C3—C6	108.33 (17)	O4—C6—H6B	109.2
N1—C3—C4	107.93 (16)	C3—C6—H6B	109.2
C6—C3—C4	110.28 (16)	H6A—C6—H6B	107.9
N1—C3—C5	108.57 (16)	C3—N1—H1A	109.5
C6—C3—C5	110.83 (16)	C3—N1—H1B	109.5
C4—C3—C5	110.81 (17)	H1A—N1—H1B	109.5
O3—C4—C3	112.12 (16)	C3—N1—H1C	109.5
O3—C4—H4A	109.2	H1A—N1—H1C	109.5
C3—C4—H4A	109.2	H1B—N1—H1C	109.5
O3—C4—H4B	109.2	C4—O3—H3	106.3
C3—C4—H4B	109.2	C6—O4—H4	109.1
H4A—C4—H4B	107.9	C5—O5—H5	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.89	2.00	2.881 (2)	169
N1—H1B···O2ii	0.89	1.97	2.858 (2)	172
N1—H1C···O5iii	0.89	2.03	2.909 (2)	169
O3—H3···O4iv	0.81	1.85	2.654 (2)	169
O4—H4···O1	0.82	1.84	2.655 (2)	173
O5—H5···O2v	0.82	1.88	2.691 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.89	2.00	2.881 (2)	169
N1—H1B⋯O2ii	0.89	1.97	2.858 (2)	172
N1—H1C⋯O5iii	0.89	2.03	2.909 (2)	169
O3—H3⋯O4iv	0.81	1.85	2.654 (2)	169
O4—H4⋯O1	0.82	1.84	2.655 (2)	173
O5—H5⋯O2v	0.82	1.88	2.691 (2)	168

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