N,N′-Bis[2-(dimethyl­ammonio)eth­yl]oxamide dinitrate

In the crystal structure of the title compound, C₁₀H₂₄N₄O₂²⁺·2NO₃⁻ or [H₄dmaeoxd](NO₃)₂ {H₂dmaeoxd is N,N′-bis­[2-(dimethyl­amino)eth­yl]oxamide}, the diprotonated H₄dmaeoxd dication occupies a special position on an inversion centre and exhibits a transoid conformation. The six non-H atoms of the oxamide group are almost exactly coplanar. Two symmetry-independent NH groups of the dication form hydrogen bonds with two O atoms belonging to one NO₃⁻ anion. Four independent C—H...O inter­actions link dications and anions into an infinite three-dimensional system.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.110
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.121
            Value of mu given      =     0.120
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C5_a   ...       1.54 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 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
   1 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-Bis[2-(dimethylammonio)ethyl]oxamide dinitrate

Crystal data

C10H24N4O2^2+·2NO3^−	F(000) = 380
Mr = 356.35	Dx = 1.414 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1371 reflections
a = 7.9809 (19) Å	θ = 2.6–24.5°
b = 8.703 (2) Å	µ = 0.12 mm^−1
c = 12.214 (3) Å	T = 298 K
β = 99.522 (3)°	Flake, colourless
V = 836.7 (3) Å^3	0.27 × 0.16 × 0.09 mm
Z = 2

Data collection

Bruker APEX area-detector diffractometer	2043 independent reflections
Radiation source: fine-focus sealed tube	1237 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→10
Tmin = 0.968, Tmax = 0.989	k = −11→9
5342 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.2517P] where P = (Fo^2 + 2Fc^2)/3
2043 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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
C1	0.7676 (2)	0.3326 (2)	0.64393 (18)	0.0549 (5)
H1A	0.6987	0.3364	0.5717	0.082*
H1B	0.7278	0.2519	0.6866	0.082*
H1C	0.8836	0.3131	0.6365	0.082*
C2	0.8063 (3)	0.6103 (3)	0.63294 (18)	0.0588 (6)
H2A	0.7972	0.7059	0.6707	0.088*
H2B	0.7323	0.6120	0.5624	0.088*
H2C	0.9214	0.5958	0.6216	0.088*
C3	0.8574 (2)	0.4862 (2)	0.81545 (14)	0.0385 (4)
H3A	0.8516	0.5889	0.8454	0.046*
H3B	0.9754	0.4649	0.8112	0.046*
C4	0.7970 (2)	0.3726 (2)	0.89383 (15)	0.0417 (4)
H4A	0.8004	0.2701	0.8632	0.050*
H4B	0.8741	0.3748	0.9641	0.050*
C5	0.5954 (2)	0.4900 (2)	0.99793 (14)	0.0377 (4)
N1	0.75648 (18)	0.48198 (17)	0.70128 (12)	0.0384 (4)
H1	0.652 (2)	0.498 (2)	0.7057 (15)	0.047 (5)*
N2	0.62595 (18)	0.40420 (17)	0.91362 (12)	0.0393 (4)
H2	0.543 (2)	0.371 (2)	0.8683 (16)	0.045 (5)*
N3	0.32280 (19)	0.4178 (2)	0.66786 (13)	0.0481 (4)
O1	0.70383 (16)	0.54755 (17)	1.06780 (11)	0.0558 (4)
O2	0.40257 (16)	0.30019 (16)	0.70225 (12)	0.0568 (4)
O3	0.16740 (17)	0.4168 (2)	0.64461 (14)	0.0815 (6)
O4	0.40383 (18)	0.53861 (18)	0.65804 (15)	0.0712 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0490 (11)	0.0570 (13)	0.0602 (12)	−0.0038 (9)	0.0137 (9)	−0.0230 (10)
C2	0.0642 (13)	0.0593 (14)	0.0573 (12)	0.0053 (11)	0.0229 (10)	0.0130 (11)
C3	0.0323 (8)	0.0397 (10)	0.0431 (10)	−0.0017 (7)	0.0051 (7)	−0.0044 (8)
C4	0.0384 (9)	0.0420 (10)	0.0452 (10)	0.0049 (8)	0.0081 (8)	−0.0003 (8)
C5	0.0395 (9)	0.0343 (9)	0.0396 (9)	−0.0007 (7)	0.0069 (7)	0.0017 (8)
N1	0.0294 (7)	0.0445 (9)	0.0431 (8)	0.0017 (6)	0.0112 (6)	−0.0017 (7)
N2	0.0348 (8)	0.0442 (9)	0.0392 (8)	−0.0027 (7)	0.0069 (7)	−0.0047 (7)
N3	0.0329 (8)	0.0650 (12)	0.0469 (9)	0.0004 (8)	0.0080 (7)	−0.0009 (8)
O1	0.0413 (7)	0.0655 (10)	0.0588 (9)	−0.0047 (6)	0.0028 (6)	−0.0222 (7)
O2	0.0482 (8)	0.0492 (9)	0.0732 (10)	0.0004 (6)	0.0111 (7)	0.0009 (7)
O3	0.0289 (7)	0.1265 (16)	0.0869 (12)	−0.0002 (8)	0.0035 (7)	0.0131 (10)
O4	0.0477 (8)	0.0538 (10)	0.1114 (13)	−0.0001 (7)	0.0110 (8)	0.0161 (9)

Geometric parameters (Å, º)

C1—N1	1.486 (2)	C4—N2	1.451 (2)
C1—H1A	0.9600	C4—H4A	0.9700
C1—H1B	0.9600	C4—H4B	0.9700
C1—H1C	0.9600	C5—O1	1.218 (2)
C2—N1	1.487 (2)	C5—N2	1.327 (2)
C2—H2A	0.9600	C5—C5^i	1.541 (3)
C2—H2B	0.9600	N1—H1	0.859 (19)
C2—H2C	0.9600	N2—H2	0.842 (19)
C3—N1	1.491 (2)	N3—O3	1.2257 (19)
C3—C4	1.510 (2)	N3—O2	1.241 (2)
C3—H3A	0.9700	N3—O4	1.251 (2)
C3—H3B	0.9700
N1—C1—H1A	109.5	C3—C4—H4A	109.0
N1—C1—H1B	109.5	N2—C4—H4B	109.0
H1A—C1—H1B	109.5	C3—C4—H4B	109.0
N1—C1—H1C	109.5	H4A—C4—H4B	107.8
H1A—C1—H1C	109.5	O1—C5—N2	125.06 (16)
H1B—C1—H1C	109.5	O1—C5—C5^i	121.5 (2)
N1—C2—H2A	109.5	N2—C5—C5^i	113.47 (18)
N1—C2—H2B	109.5	C1—N1—C2	110.48 (15)
H2A—C2—H2B	109.5	C1—N1—C3	113.41 (15)
N1—C2—H2C	109.5	C2—N1—C3	110.68 (15)
H2A—C2—H2C	109.5	C1—N1—H1	107.7 (13)
H2B—C2—H2C	109.5	C2—N1—H1	105.6 (13)
N1—C3—C4	113.39 (14)	C3—N1—H1	108.6 (12)
N1—C3—H3A	108.9	C5—N2—C4	122.31 (15)
C4—C3—H3A	108.9	C5—N2—H2	118.8 (12)
N1—C3—H3B	108.9	C4—N2—H2	118.9 (12)
C4—C3—H3B	108.9	O3—N3—O2	121.01 (18)
H3A—C3—H3B	107.7	O3—N3—O4	120.21 (18)
N2—C4—C3	112.93 (14)	O2—N3—O4	118.77 (15)
N2—C4—H4A	109.0

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.859 (19)	1.998 (19)	2.820 (2)	159.7 (17)
N2—H2···O2	0.842 (19)	2.23 (2)	3.023 (2)	156.1 (16)
C1—H1C···O3^ii	0.96	2.42	3.272 (2)	147
C2—H2C···O3^ii	0.96	2.49	3.321 (3)	145
C2—H2A···O2^iii	0.96	2.54	3.267 (3)	133
C4—H4A···O4^iv	0.97	2.58	3.329 (3)	135

Symmetry codes: (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2.