N,N'-Bis[2-(methoxycarbonyl)ethyl]ethane-1,2-diammonium dichloride.

In the crystal structure of the title compound, C(10)H(22)N(2)O(4) (2+)·2Cl(-) or (H(2)Me(2)eddp)Cl(2) (H(2)Me(2)eddp(2+) is the dimethyl N,N'-di-3-propane-carboxylato-ethane-1,2-diyldiimin-ium cation), the packing is stabilized by an infinite two-dimensional ⋯Cl⋯H-N-H⋯Cl⋯ hydrogen-bonding network. In addition, short C-H⋯Cl contacts are observed.

Related literature

For related literature, see: Aakeröy et al. (1999 ▶); Bruhn et al. (2008 ▶); Kaluderović & Sabo (2002 ▶); Kaluderović et al. (2005 ▶, 2007 ▶, 2008 ▶); Krajčinović et al. (2008 ▶); Mijatović et al. (2005 ▶).

Experimental

Crystal data

C10H22N2O4 2+·2Cl−

M = 305.20

Monoclinic,

a = 8.9030 (8) Å

b = 10.3327 (10) Å

c = 8.3269 (10) Å

β = 101.763 (10)°

V = 749.93 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 293 (2) K

0.42 × 0.12 × 0.10 mm

Data collection

Stoe STADI4 diffractometer

Absorption correction: none

5296 measured reflections

1324 independent reflections

1021 reflections with I > 2σ(I)

R int = 0.057

2 standard reflections frequency: 60 min intensity decay: random variation ±5%

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.13

1324 reflections

116 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: STADI4 (Stoe & Cie, 1996 ▶); cell refinement: STADI4; data reduction: STADI4; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016565/pk2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016565/pk2097Isup2.hkl

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

C10H22N2O42+·2Cl–	F000 = 324
Mr = 305.20	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 26 reflections
a = 8.9030 (8) Å	θ = 7.7–12.2º
b = 10.3327 (10) Å	µ = 0.44 mm−1
c = 8.3269 (10) Å	T = 293 (2) K
β = 101.763 (10)º	Needle, colourless
V = 749.93 (13) Å3	0.42 × 0.12 × 0.10 mm
Z = 2

Stoe STADI4 diffractometer	Rint = 0.057
Radiation source: fine-focus sealed tube	θmax = 25.1º
Monochromator: graphite	θmin = 2.3º
T = 293(2) K	h = −10→10
ω/2θ scans	k = −12→12
Absorption correction: none	l = −9→9
5296 measured reflections	2 standard reflections
1324 independent reflections	every 60 min
1021 reflections with I > 2σ(I)	intensity decay: random variation +−5%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0263P)2 + 0.2601P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.24 e Å−3
1324 reflections	Δρmin = −0.22 e Å−3
116 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)
Secondary atom site location: difference Fourier map

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
C1	0.5853 (3)	0.4998 (2)	0.5051 (3)	0.0387 (6)
H2	0.624 (3)	0.586 (2)	0.507 (3)	0.046 (7)*
H1	0.636 (3)	0.454 (2)	0.596 (3)	0.051 (7)*
C2	0.7898 (3)	0.4385 (3)	0.3579 (3)	0.0401 (6)
H5	0.835 (3)	0.409 (2)	0.462 (3)	0.052 (8)*
H6	0.818 (3)	0.525 (3)	0.344 (3)	0.046 (7)*
C3	0.8277 (3)	0.3565 (3)	0.2221 (3)	0.0421 (6)
H8	0.756 (3)	0.376 (2)	0.126 (3)	0.047 (7)*
H7	0.819 (3)	0.272 (2)	0.248 (3)	0.045 (7)*
C4	0.9857 (3)	0.3853 (2)	0.1953 (3)	0.0417 (6)
C5	1.1771 (3)	0.3294 (3)	0.0491 (3)	0.0609 (8)
H9	1.1942	0.4207	0.0408	0.091*
H11	1.1832	0.2882	−0.0528	0.091*
H10	1.2539	0.2937	0.1356	0.091*
N	0.6217 (2)	0.43799 (19)	0.3563 (3)	0.0345 (5)
H3	0.585 (3)	0.349 (3)	0.352 (3)	0.051 (7)*
H4	0.577 (3)	0.480 (2)	0.271 (3)	0.047 (8)*
O1	1.0669 (2)	0.4681 (2)	0.2636 (3)	0.0799 (7)
O2	1.02593 (19)	0.30760 (17)	0.0849 (2)	0.0566 (5)
Cl	0.49596 (7)	0.66139 (5)	0.11984 (7)	0.0475 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0311 (12)	0.0375 (13)	0.0491 (15)	−0.0017 (10)	0.0122 (11)	−0.0005 (11)
C2	0.0277 (12)	0.0450 (15)	0.0488 (15)	−0.0014 (10)	0.0104 (11)	−0.0051 (12)
C3	0.0363 (13)	0.0453 (16)	0.0444 (14)	−0.0044 (11)	0.0076 (11)	−0.0059 (12)
C4	0.0340 (13)	0.0505 (14)	0.0390 (13)	0.0011 (11)	0.0038 (10)	−0.0028 (11)
C5	0.0503 (16)	0.0728 (19)	0.0679 (18)	0.0073 (14)	0.0312 (14)	−0.0037 (16)
N	0.0272 (10)	0.0305 (10)	0.0461 (12)	0.0013 (8)	0.0080 (8)	0.0056 (9)
O1	0.0440 (11)	0.1084 (17)	0.0928 (16)	−0.0259 (12)	0.0270 (11)	−0.0537 (14)
O2	0.0499 (11)	0.0618 (12)	0.0648 (12)	−0.0047 (9)	0.0271 (9)	−0.0190 (9)
Cl	0.0542 (4)	0.0336 (3)	0.0529 (4)	0.0092 (3)	0.0064 (3)	0.0026 (3)

C1—N	1.487 (3)	C3—H7	0.91 (2)
C1—C1i	1.505 (4)	C4—O1	1.188 (3)
C1—H2	0.95 (2)	C4—O2	1.324 (3)
C1—H1	0.93 (3)	C5—O2	1.454 (3)
C2—N	1.494 (3)	C5—H9	0.9600
C2—C3	1.506 (3)	C5—H11	0.9600
C2—H5	0.93 (2)	C5—H10	0.9600
C2—H6	0.94 (3)	N—H3	0.97 (3)
C3—C4	1.498 (3)	N—H4	0.85 (3)
C3—H8	0.94 (2)
N—C1—C1i	110.0 (3)	H8—C3—H7	109 (2)
N—C1—H2	105.7 (14)	O1—C4—O2	123.0 (2)
C1i—C1—H2	111.0 (14)	O1—C4—C3	124.8 (2)
N—C1—H1	107.8 (15)	O2—C4—C3	112.2 (2)
C1i—C1—H1	111.5 (15)	O2—C5—H9	109.5
H2—C1—H1	111 (2)	O2—C5—H11	109.5
N—C2—C3	111.63 (19)	H9—C5—H11	109.5
N—C2—H5	104.7 (15)	O2—C5—H10	109.5
C3—C2—H5	113.1 (16)	H9—C5—H10	109.5
N—C2—H6	107.3 (15)	H11—C5—H10	109.5
C3—C2—H6	109.6 (15)	C1—N—C2	112.25 (18)
H5—C2—H6	110 (2)	C1—N—H3	108.0 (14)
C4—C3—C2	111.1 (2)	C2—N—H3	109.2 (14)
C4—C3—H8	108.8 (14)	C1—N—H4	109.2 (17)
C2—C3—H8	107.9 (15)	C2—N—H4	107.4 (16)
C4—C3—H7	110.7 (15)	H3—N—H4	111 (2)
C2—C3—H7	109.0 (15)	C4—O2—C5	116.20 (19)
N—C2—C3—C4	164.5 (2)	C3—C2—N—C1	170.4 (2)
C2—C3—C4—O1	−5.0 (4)	O1—C4—O2—C5	−0.5 (4)
C2—C3—C4—O2	175.3 (2)	C3—C4—O2—C5	179.2 (2)
C1i—C1—N—C2	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H3···Clii	0.97 (3)	2.10 (3)	3.064 (2)	171 (2)
N—H4···Cl	0.85 (2)	2.30 (2)	3.092 (2)	156 (2)
C3—H8···Cliii	0.95 (2)	2.73 (3)	3.619 (3)	156.3 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H3⋯Cli	0.97 (3)	2.10 (3)	3.064 (2)	171 (2)
N—H4⋯Cl	0.85 (2)	2.30 (2)	3.092 (2)	156 (2)
C3—H8⋯Clii	0.95 (2)	2.73 (3)	3.619 (3)	156.3 (18)

Symmetry codes: (i) ; (ii) .