organic compounds
Bis[diamino(ethoxycarbonylamino)methylium] sulfate
aUniversity of Sargodha, Department of Physics, Sagrodha, Pakistan, bDepartment of Chemistry, FC College University, Lahore, Pakistan, cUniversity of Sargodha, Department of Chemistry, Sagrodha, Pakistan, and dHacettepe University, Department of Physics Engineering, Beytepe 06532, Ankara, Turkey
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the molecule of the title compound, 2C4H10N3O2+·SO4−, the cations are planar (r.m.s. deviations = 0.0144 and 0.0236 Å) and oriented at a dihedral angle of 62.30 (4)°. Intramolecular N—H⋯O hydrogen bonds result in the formation of two planar six-membered rings. The cations are linked to the sulfate ion through intermolecular C—H⋯O and N—H⋯O hydrogen bonds, forming an R22(8) ring motif. In the intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.
Related literature
For related structures, see: Brauer & Kottsieper (2003); Curtis & Pasternak (1955). For bond-length data, see: Allen et al. (1987). For ring motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Supporting information
10.1107/S160053680900912X/hk2641sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680900912X/hk2641Isup2.hkl
For the preparation of the title compound, 1-cyanoguanidine (2.1 g, 0.025 mol) was dissolved in water (50 ml), and then a few drops of H2SO4 were added. The resulting mixture was refluxed for 2–3 h, and cooled to room temperature. The excess of ethanol was added, and then refluxed for 2–3 h. It was filtered through alumina. The filtrate was concentrated under reduced pressure and kept for crystallization. Recrystallization was carried out from ethanol/hexane (9:1) mixture in 5 d.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Hydrogen bonds are shown as dashed lines. | |
Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. |
2C4H10N3O2+·SO42− | F(000) = 760 |
Mr = 360.36 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.3021 (12) Å | θ = 10.0–18.2° |
b = 11.0081 (11) Å | µ = 0.24 mm−1 |
c = 17.1063 (13) Å | T = 296 K |
β = 100.980 (3)° | Prism, colourless |
V = 1719.6 (3) Å3 | 0.24 × 0.18 × 0.15 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2124 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.3°, θmin = 2.2° |
ω/2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
Tmin = 0.946, Tmax = 0.967 | l = −21→20 |
3481 measured reflections | 3 standard reflections every 120 min |
3481 independent reflections | intensity decay: 1.7% |
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)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.1093P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3481 reflections | Δρmax = 0.21 e Å−3 |
233 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (9) |
2C4H10N3O2+·SO42− | V = 1719.6 (3) Å3 |
Mr = 360.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3021 (12) Å | µ = 0.24 mm−1 |
b = 11.0081 (11) Å | T = 296 K |
c = 17.1063 (13) Å | 0.24 × 0.18 × 0.15 mm |
β = 100.980 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2124 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.946, Tmax = 0.967 | 3 standard reflections every 120 min |
3481 measured reflections | intensity decay: 1.7% |
3481 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.21 e Å−3 |
3481 reflections | Δρmin = −0.25 e Å−3 |
233 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | ||
S1 | 0.74538 (6) | 0.22561 (5) | 0.25630 (4) | 0.0324 (2) | |
O1 | 0.87642 (18) | 0.15672 (16) | 0.29258 (11) | 0.0494 (6) | |
O2 | 0.78056 (17) | 0.35534 (15) | 0.25361 (10) | 0.0398 (6) | |
O3 | 0.6301 (2) | 0.20989 (17) | 0.30259 (11) | 0.0536 (7) | |
O4 | 0.6925 (2) | 0.18149 (16) | 0.17468 (10) | 0.0492 (7) | |
O5 | 0.43306 (19) | 0.28294 (17) | 0.43071 (11) | 0.0499 (6) | |
O6 | 0.53979 (17) | 0.45797 (16) | 0.40549 (11) | 0.0471 (6) | |
O7 | 0.2706 (2) | 0.42933 (17) | −0.03291 (11) | 0.0560 (7) | |
O8 | 0.17269 (19) | 0.60725 (16) | −0.00697 (10) | 0.0460 (6) | |
N1 | 0.0671 (3) | 0.4461 (2) | 0.29228 (14) | 0.0499 (8) | |
N2 | 0.1472 (3) | 0.2719 (2) | 0.35872 (15) | 0.0529 (9) | |
N3 | 0.3058 (2) | 0.43420 (19) | 0.35471 (12) | 0.0422 (7) | |
N4 | 0.5287 (3) | 0.4909 (2) | 0.19080 (14) | 0.0500 (8) | |
N5 | 0.4929 (3) | 0.3569 (2) | 0.08613 (14) | 0.0480 (8) | |
N6 | 0.3530 (2) | 0.53306 (19) | 0.08234 (12) | 0.0426 (7) | |
C1 | 0.1711 (3) | 0.3811 (2) | 0.33493 (15) | 0.0382 (8) | |
C2 | 0.4290 (3) | 0.3811 (2) | 0.40006 (15) | 0.0381 (8) | |
C3 | 0.6785 (3) | 0.4149 (3) | 0.45146 (17) | 0.0532 (10) | |
C4 | 0.7871 (3) | 0.5128 (3) | 0.4471 (2) | 0.0807 (15) | |
C5 | 0.4611 (3) | 0.4578 (2) | 0.11953 (15) | 0.0376 (8) | |
C6 | 0.2642 (3) | 0.5151 (3) | 0.00936 (15) | 0.0387 (8) | |
C7 | 0.0712 (3) | 0.6005 (3) | −0.08355 (15) | 0.0502 (10) | |
C8 | −0.0188 (4) | 0.7126 (3) | −0.0906 (2) | 0.0738 (12) | |
H1A | 0.090 (3) | 0.518 (3) | 0.2665 (16) | 0.0599* | |
H1B | −0.020 (3) | 0.421 (3) | 0.2797 (17) | 0.0599* | |
H2A | 0.215 (3) | 0.234 (3) | 0.3859 (18) | 0.0634* | |
H2B | 0.059 (3) | 0.237 (3) | 0.3410 (17) | 0.0634* | |
H3A | 0.70789 | 0.34004 | 0.42905 | 0.0638* | |
H3B | 0.67011 | 0.40013 | 0.50630 | 0.0638* | |
H4A | 0.88070 | 0.48943 | 0.47744 | 0.0965* | |
H4B | 0.75542 | 0.58660 | 0.46846 | 0.0965* | |
H4C | 0.79518 | 0.52545 | 0.39258 | 0.0965* | |
H4D | 0.499 (3) | 0.563 (3) | 0.2083 (16) | 0.0600* | |
H4E | 0.608 (3) | 0.445 (3) | 0.2123 (16) | 0.0600* | |
H5 | 0.31494 | 0.50670 | 0.33757 | 0.0505* | |
H5A | 0.446 (3) | 0.337 (3) | 0.0435 (17) | 0.0576* | |
H5B | 0.560 (3) | 0.303 (3) | 0.1145 (16) | 0.0576* | |
H6 | 0.33899 | 0.59866 | 0.10715 | 0.0511* | |
H7A | 0.00927 | 0.52921 | −0.08540 | 0.0602* | |
H7B | 0.12481 | 0.59560 | −0.12684 | 0.0602* | |
H8A | −0.09353 | 0.70817 | −0.13771 | 0.0883* | |
H8B | 0.04250 | 0.78183 | −0.09397 | 0.0883* | |
H8C | −0.06354 | 0.72035 | −0.04471 | 0.0883* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0322 (3) | 0.0241 (3) | 0.0383 (4) | −0.0023 (3) | −0.0001 (3) | 0.0012 (3) |
O1 | 0.0432 (11) | 0.0334 (10) | 0.0616 (12) | 0.0064 (9) | −0.0152 (9) | −0.0021 (9) |
O2 | 0.0347 (9) | 0.0263 (9) | 0.0566 (11) | −0.0042 (7) | 0.0041 (8) | 0.0042 (8) |
O3 | 0.0547 (12) | 0.0461 (12) | 0.0647 (12) | −0.0088 (10) | 0.0234 (10) | 0.0106 (10) |
O4 | 0.0594 (12) | 0.0378 (11) | 0.0425 (11) | 0.0086 (9) | −0.0106 (9) | −0.0060 (8) |
O5 | 0.0432 (10) | 0.0396 (11) | 0.0625 (12) | −0.0056 (9) | −0.0011 (9) | 0.0182 (10) |
O6 | 0.0315 (9) | 0.0409 (11) | 0.0639 (12) | −0.0073 (8) | −0.0032 (8) | 0.0060 (9) |
O7 | 0.0609 (12) | 0.0462 (12) | 0.0535 (12) | 0.0160 (10) | −0.0080 (9) | −0.0187 (10) |
O8 | 0.0512 (11) | 0.0440 (11) | 0.0394 (10) | 0.0178 (9) | 0.0002 (8) | −0.0017 (9) |
N1 | 0.0359 (12) | 0.0444 (15) | 0.0620 (16) | −0.0101 (12) | −0.0097 (12) | 0.0166 (12) |
N2 | 0.0430 (14) | 0.0397 (15) | 0.0673 (16) | −0.0156 (12) | −0.0113 (12) | 0.0165 (12) |
N3 | 0.0344 (11) | 0.0336 (13) | 0.0537 (13) | −0.0085 (10) | −0.0036 (10) | 0.0124 (10) |
N4 | 0.0540 (15) | 0.0426 (15) | 0.0466 (14) | 0.0216 (12) | −0.0074 (11) | −0.0097 (12) |
N5 | 0.0548 (15) | 0.0379 (14) | 0.0451 (14) | 0.0159 (12) | −0.0062 (11) | −0.0088 (12) |
N6 | 0.0498 (13) | 0.0340 (12) | 0.0408 (12) | 0.0139 (11) | 0.0006 (10) | −0.0078 (10) |
C1 | 0.0365 (14) | 0.0356 (16) | 0.0394 (14) | −0.0084 (12) | −0.0004 (11) | 0.0031 (12) |
C2 | 0.0367 (14) | 0.0365 (16) | 0.0394 (14) | −0.0071 (12) | 0.0033 (11) | 0.0010 (12) |
C3 | 0.0355 (15) | 0.0536 (19) | 0.0644 (19) | −0.0006 (14) | −0.0058 (13) | −0.0074 (15) |
C4 | 0.0395 (17) | 0.093 (3) | 0.105 (3) | −0.0204 (18) | 0.0024 (17) | −0.012 (2) |
C5 | 0.0391 (14) | 0.0342 (15) | 0.0388 (15) | 0.0066 (12) | 0.0055 (12) | −0.0001 (12) |
C6 | 0.0396 (14) | 0.0345 (15) | 0.0417 (15) | 0.0051 (12) | 0.0069 (12) | −0.0004 (13) |
C7 | 0.0500 (16) | 0.0579 (19) | 0.0384 (15) | 0.0098 (15) | −0.0022 (12) | 0.0020 (14) |
C8 | 0.070 (2) | 0.075 (2) | 0.070 (2) | 0.032 (2) | −0.0028 (17) | 0.0115 (19) |
S1—O3 | 1.460 (2) | N5—C5 | 1.308 (3) |
S1—O4 | 1.4716 (18) | N6—C5 | 1.363 (3) |
S1—O1 | 1.4690 (19) | N6—C6 | 1.374 (3) |
S1—O2 | 1.4678 (17) | N4—H4E | 0.91 (3) |
O5—C2 | 1.199 (3) | N4—H4D | 0.91 (3) |
O6—C3 | 1.457 (3) | N5—H5B | 0.93 (3) |
O6—C2 | 1.323 (3) | N5—H5A | 0.81 (3) |
O7—C6 | 1.198 (4) | N6—H6 | 0.8600 |
O8—C6 | 1.320 (4) | C3—C4 | 1.489 (4) |
O8—C7 | 1.464 (3) | C3—H3A | 0.9700 |
N1—C1 | 1.308 (4) | C3—H3B | 0.9700 |
N2—C1 | 1.302 (3) | C4—H4C | 0.9600 |
N3—C2 | 1.385 (3) | C4—H4B | 0.9600 |
N3—C1 | 1.366 (3) | C4—H4A | 0.9600 |
N1—H1A | 0.95 (3) | C7—C8 | 1.483 (5) |
N1—H1B | 0.84 (3) | C7—H7A | 0.9700 |
N2—H2A | 0.82 (3) | C7—H7B | 0.9700 |
N2—H2B | 0.90 (3) | C8—H8B | 0.9600 |
N3—H5 | 0.8600 | C8—H8C | 0.9600 |
N4—C5 | 1.312 (3) | C8—H8A | 0.9600 |
S1···H2Bi | 3.00 (3) | N4···O2 | 2.813 (3) |
S1···H4E | 2.77 (3) | N5···O4 | 2.898 (3) |
S1···H5B | 2.83 (3) | N5···O7 | 2.730 (3) |
S1···H1Aii | 2.82 (3) | N5···C6v | 3.341 (4) |
S1···H4Dii | 3.04 (3) | N5···O5iv | 3.031 (3) |
S1···H5ii | 2.8900 | N6···O3vii | 2.752 (3) |
S1···H6ii | 2.9500 | C2···O3 | 3.320 (3) |
S1···H1Bi | 3.04 (3) | C3···O3 | 3.368 (4) |
O1···N2i | 2.854 (3) | C5···O3vii | 3.260 (3) |
O1···N1ii | 2.837 (3) | C5···O7v | 3.373 (3) |
O2···N1i | 2.805 (3) | C6···N5v | 3.341 (4) |
O2···N4 | 2.813 (3) | C2···H4Bviii | 3.1000 |
O3···C2 | 3.320 (3) | C2···H2A | 2.54 (3) |
O3···N4ii | 2.841 (3) | C6···H5A | 2.58 (3) |
O3···C5ii | 3.260 (3) | H1A···S1vii | 2.82 (3) |
O3···C3 | 3.368 (4) | H1A···O1vii | 1.89 (3) |
O3···O5 | 3.216 (3) | H1A···H5 | 2.2100 |
O3···N6ii | 2.752 (3) | H1A···O4vii | 2.75 (3) |
O4···N5 | 2.898 (3) | H1B···S1vi | 3.04 (3) |
O4···N3ii | 2.769 (3) | H1B···H2B | 2.33 (5) |
O5···O7iii | 2.914 (3) | H1B···O2vi | 1.96 (3) |
O5···O3 | 3.216 (3) | H2A···O7iii | 2.27 (3) |
O5···N2 | 2.712 (3) | H2A···C2 | 2.54 (3) |
O5···N5iii | 3.031 (3) | H2A···O5 | 2.10 (3) |
O7···O5iv | 2.914 (3) | H2B···O1vi | 1.95 (3) |
O7···N5 | 2.730 (3) | H2B···H1B | 2.33 (5) |
O7···N2iv | 2.975 (3) | H2B···S1vi | 3.00 (3) |
O7···C5v | 3.373 (3) | H3A···O5 | 2.6400 |
O1···H2Bi | 1.95 (3) | H3A···O3 | 2.5800 |
O1···H1Aii | 1.89 (3) | H3B···O5 | 2.6700 |
O2···H1Bi | 1.96 (3) | H4A···H4Aix | 2.2200 |
O2···H5B | 2.89 (3) | H4B···C2viii | 3.1000 |
O2···H4E | 1.90 (3) | H4D···S1vii | 3.04 (3) |
O2···H7Bv | 2.5500 | H4D···H6 | 2.0900 |
O3···H3A | 2.5800 | H4D···O3vii | 2.00 (3) |
O3···H4Dii | 2.00 (3) | H4E···S1 | 2.77 (3) |
O3···H6ii | 1.9500 | H4E···H5B | 2.27 (4) |
O4···H5B | 1.97 (3) | H4E···O2 | 1.90 (3) |
O4···H1Aii | 2.75 (3) | H5···H1A | 2.2100 |
O4···H5ii | 1.9400 | H5···S1vii | 2.8900 |
O5···H3A | 2.6400 | H5···O4vii | 1.9400 |
O5···H3B | 2.6700 | H5A···C6 | 2.58 (3) |
O5···H5Aiii | 2.32 (3) | H5A···O5iv | 2.32 (3) |
O5···H2A | 2.10 (3) | H5A···O7 | 2.14 (3) |
O7···H7B | 2.6300 | H5B···O2 | 2.89 (3) |
O7···H7A | 2.6600 | H5B···O4 | 1.97 (3) |
O7···H5A | 2.14 (3) | H5B···S1 | 2.83 (3) |
O7···H2Aiv | 2.27 (3) | H5B···H4E | 2.27 (4) |
N1···O2vi | 2.805 (3) | H6···S1vii | 2.9500 |
N1···O1vii | 2.837 (3) | H6···O3vii | 1.9500 |
N2···O1vi | 2.854 (3) | H6···H4D | 2.0900 |
N2···O5 | 2.712 (3) | H7A···O7 | 2.6600 |
N2···O7iii | 2.975 (3) | H7B···O7 | 2.6300 |
N3···O4vii | 2.769 (3) | H7B···O2v | 2.5500 |
N4···O3vii | 2.841 (3) | ||
O3—S1—O4 | 109.16 (11) | O5—C2—N3 | 125.4 (2) |
O1—S1—O3 | 110.23 (11) | O6—C3—C4 | 106.1 (2) |
O1—S1—O4 | 109.33 (11) | H3A—C3—H3B | 109.00 |
O1—S1—O2 | 110.09 (10) | O6—C3—H3B | 111.00 |
O2—S1—O4 | 109.12 (10) | O6—C3—H3A | 111.00 |
O2—S1—O3 | 108.88 (10) | C4—C3—H3A | 111.00 |
C2—O6—C3 | 115.3 (2) | C4—C3—H3B | 111.00 |
C6—O8—C7 | 115.5 (2) | C3—C4—H4C | 109.00 |
C1—N3—C2 | 125.5 (2) | H4A—C4—H4B | 109.00 |
C1—N1—H1A | 120.5 (17) | H4A—C4—H4C | 109.00 |
C1—N1—H1B | 122 (2) | C3—C4—H4A | 109.00 |
H1A—N1—H1B | 116 (3) | C3—C4—H4B | 109.00 |
C1—N2—H2A | 119 (2) | H4B—C4—H4C | 109.00 |
C1—N2—H2B | 119 (2) | N4—C5—N5 | 122.2 (2) |
H2A—N2—H2B | 122 (3) | N4—C5—N6 | 116.4 (2) |
C2—N3—H5 | 117.00 | N5—C5—N6 | 121.3 (2) |
C1—N3—H5 | 117.00 | O7—C6—N6 | 124.9 (3) |
C5—N6—C6 | 126.8 (2) | O7—C6—O8 | 125.6 (2) |
C5—N4—H4E | 115.4 (18) | O8—C6—N6 | 109.5 (2) |
H4D—N4—H4E | 129 (3) | O8—C7—C8 | 106.8 (2) |
C5—N4—H4D | 115.2 (17) | C8—C7—H7A | 110.00 |
C5—N5—H5B | 120.0 (18) | C8—C7—H7B | 110.00 |
C5—N5—H5A | 120 (2) | O8—C7—H7A | 110.00 |
H5A—N5—H5B | 120 (3) | O8—C7—H7B | 110.00 |
C6—N6—H6 | 117.00 | H7A—C7—H7B | 109.00 |
C5—N6—H6 | 117.00 | H8B—C8—H8C | 109.00 |
N2—C1—N3 | 121.4 (2) | C7—C8—H8A | 109.00 |
N1—C1—N3 | 116.8 (2) | C7—C8—H8B | 109.00 |
N1—C1—N2 | 121.8 (3) | C7—C8—H8C | 109.00 |
O6—C2—N3 | 108.65 (19) | H8A—C8—H8B | 109.00 |
O5—C2—O6 | 125.9 (2) | H8A—C8—H8C | 109.00 |
C3—O6—C2—O5 | 1.9 (4) | C2—N3—C1—N2 | 0.4 (4) |
C3—O6—C2—N3 | −179.8 (2) | C1—N3—C2—O5 | −3.0 (4) |
C2—O6—C3—C4 | 178.0 (2) | C1—N3—C2—O6 | 178.6 (2) |
C6—O8—C7—C8 | −179.0 (2) | C6—N6—C5—N4 | −177.4 (3) |
C7—O8—C6—O7 | 0.5 (4) | C6—N6—C5—N5 | 1.2 (4) |
C7—O8—C6—N6 | 179.8 (2) | C5—N6—C6—O7 | −0.7 (4) |
C2—N3—C1—N1 | 179.2 (2) | C5—N6—C6—O8 | 180.0 (2) |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+1, −z; (vi) x−1, y, z; (vii) −x+1, y+1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1vii | 0.95 (3) | 1.89 (3) | 2.837 (3) | 175 (3) |
N1—H1B···O2vi | 0.84 (3) | 1.96 (3) | 2.805 (3) | 177 (3) |
N2—H2A···O5 | 0.82 (3) | 2.10 (3) | 2.712 (3) | 131 (3) |
N2—H2A···O7iii | 0.82 (3) | 2.27 (3) | 2.975 (3) | 144 (3) |
N2—H2B···O1vi | 0.90 (3) | 1.95 (3) | 2.854 (3) | 174 (3) |
N4—H4D···O3vii | 0.91 (3) | 2.00 (3) | 2.841 (3) | 153 (2) |
N4—H4E···O2 | 0.91 (3) | 1.90 (3) | 2.813 (3) | 176 (3) |
N3—H5···O4vii | 0.86 | 1.94 | 2.769 (3) | 163 |
N5—H5A···O7 | 0.81 (3) | 2.14 (3) | 2.730 (3) | 130 (3) |
N5—H5A···O5iv | 0.81 (3) | 2.32 (3) | 3.031 (3) | 147 (3) |
N5—H5B···O4 | 0.93 (3) | 1.97 (3) | 2.898 (3) | 177 (3) |
N6—H6···O3vii | 0.86 | 1.95 | 2.752 (3) | 155 |
C3—H3A···O3 | 0.97 | 2.58 | 3.368 (4) | 138 |
C7—H7B···O2v | 0.97 | 2.55 | 3.483 (3) | 162 |
Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+1, −z; (vi) x−1, y, z; (vii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | 2C4H10N3O2+·SO42− |
Mr | 360.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.3021 (12), 11.0081 (11), 17.1063 (13) |
β (°) | 100.980 (3) |
V (Å3) | 1719.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.24 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.946, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3481, 3481, 2124 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.624 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.108, 1.03 |
No. of reflections | 3481 |
No. of parameters | 233 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.25 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.95 (3) | 1.89 (3) | 2.837 (3) | 175 (3) |
N1—H1B···O2ii | 0.84 (3) | 1.96 (3) | 2.805 (3) | 177 (3) |
N2—H2A···O5 | 0.82 (3) | 2.10 (3) | 2.712 (3) | 131 (3) |
N2—H2A···O7iii | 0.82 (3) | 2.27 (3) | 2.975 (3) | 144 (3) |
N2—H2B···O1ii | 0.90 (3) | 1.95 (3) | 2.854 (3) | 174 (3) |
N4—H4D···O3i | 0.91 (3) | 2.00 (3) | 2.841 (3) | 153 (2) |
N4—H4E···O2 | 0.91 (3) | 1.90 (3) | 2.813 (3) | 176 (3) |
N3—H5···O4i | 0.86 | 1.94 | 2.769 (3) | 163 |
N5—H5A···O7 | 0.81 (3) | 2.14 (3) | 2.730 (3) | 130 (3) |
N5—H5A···O5iv | 0.81 (3) | 2.32 (3) | 3.031 (3) | 147 (3) |
N5—H5B···O4 | 0.93 (3) | 1.97 (3) | 2.898 (3) | 177 (3) |
N6—H6···O3i | 0.86 | 1.95 | 2.752 (3) | 155 |
C3—H3A···O3 | 0.97 | 2.58 | 3.368 (4) | 138 |
C7—H7B···O2v | 0.97 | 2.55 | 3.483 (3) | 162 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) x, −y+1/2, z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y+1, −z. |
Acknowledgements
The authors acknowledge the preparative efforts of the late Muhammad Asghar, student of Dr Christy Munir at Quaid-i-Azam University, Islamabad, Pakistan.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of our ongoing studies, we report herein the crystal structure of the title compound, (I).
The crystal structures of 1-carbamoylguanidinium methylphosphonate monohydrate, (II) (Brauer & Kottsieper, 2003) and methylguanidinium nitrate, (III) (Curtis & Pasternak, 1955) have been reported. In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles of the diamino(ethoxycarbonylamino)methylium (DEAM) moieties are within normal ranges. DEAM moieties (N1–N3/O5/O6/C1–C4) and (N4–N6/O7/O8/C5–C8) are planar with maximum deviations of 0.043 (2) and -0.322 (3) Å for N2 and N4 atoms, respectively, in which they are oriented at a dihedral angle of 62.30 (4)°. The intramolecular N—H···O hydrogen bonds result in the formations of two planar six-membered rings: A (O5/N2/N3/C1/C2/H2A) and B (O7/N5/N6/C5/C6/H5A). The dihedral angle between them is A/B = 60.38 (3)°. The DEAM moieties are linked to the SO4 ion through the intramolecular C—H···O and N—H···O hydrogen bonds (Table 1), forming a R22(8) ring motif (Bernstein et al., 1995).
In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.