Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 8| August 2006| Pages o476-o477
doi:10.1107/S0108270106020580

1-(Iso­propyl­­idene­amino)guanidinium 2-nitro­benzoate: formation of corrugated sheets from R22(8) and R64(16) rings

CROSSMARK_Color_square_no_text.svg
Janet M. S. Skakle,a* James L. Wardellb and Solange M. S. V. Wardellc

aDepartment of Chemistry, College of Physical Sciences, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, bDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, and cFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos, Departamento de Síntese Orgânica, Manguinhos, CEP 21041-250 Rio de Janeiro, RJ, Brazil
*Correspondence e-mail: j.skakle@abdn.ac.uk

(Received 19 April 2006; accepted 31 May 2006; online 14 July 2006)

In the title compound, C4H11N4+·C7H4NO4−, the guanidinium cation acts as a strong hydrogen-bonding donor via the guanidine NH2 and NH groups, with the carb­oxy groups of the nitro­benzoate group acting as the acceptors. These hydrogen bonds lead to fused R22(8) and R64(16) rings, which form corrugated sheets perpendicular to [010].

Comment

Some of us have previously reported the supra­molecular arrangements of anilinium salts of arenecarboxyl­ates (e.g. Glidewell et al., 2003[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o509-o511.], 2005a[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005a). Acta Cryst. C61, o246-o248.],b[Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005b). Acta Cryst. C61, o276-o280.]). We now report the structure and supra­molecular arrangement of the title compound, [(H2N)2C—NH—N=CMe2]+·[2-O2NC6H4CO2]−, (I)[link].

[Scheme 1]

The crystal structure solution confirms the presence of a salt composed of a 2-nitro­benzoate anion and a [(H2N)2CNH—N=CMe2]+ cation. The adjacent positions of the carb­oxy and nitro groups in the nitro­benzoate anion lead to both groups twisting away from the plane; the latter is twisted at an angle of 24.72 (15)°, whereas the carb­oxy group is more nearly perpendicular, at 71.18°, as can be seen in Fig. 1[link]. The 1-(isopropylideneamino)guanidinium complex is nearly planar, with an r.m.s. deviation of 0.0635 Å, and atom N4 shows the largest deviation from planarity [0.1256 (16) Å]. The angle between the plane defined by this mol­ecule and that of the 2-nitro­benzoate ring is 72.17 (7)°. A complex strong hydrogen-bonding scheme operates between the cation and the anion (Table 1[link]). The guanidinium N atoms act as donors, with the carb­oxyate O atoms the acceptors.

Two main motifs dominate the hydrogen bonding in (I)[link]. Firstly, a nearly symmetrical simple R22(8) ring (Bernstein et al., 1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) forms from hydrogen bonding between the two mol­ecules, involving the two guanidinium amino groups and the two carb­oxylate O atoms, viz. N2—H2A⋯O1 and N3—H3A⋯O2 (Fig. 1[link]). These simple dimeric rings are linked by the other hydrogen bonds to form corrugated sheets (Fig. 2[link]).

The carb­oxylate O atoms are central to the hydrogen-bonding scheme, and both act as multiple acceptors. As well as acting as an acceptor in the dimer described above, carbox­ylate atom O1 acts as a double acceptor to other guanidinium donors, viz. N3—H3B⋯O1ii and N4—H4A⋯O1ii [symmetry code: (ii) x − [{1\over 2}], −y + [{1\over 2}], z + [{1\over 2}]]. The other carb­oxylate O atom, O2, also is an acceptor for the guanidinium donor, viz. N2—H2B⋯O2i [symmetry code: (i) x − [{1\over 2}], −y + [{1\over 2}], z − [{1\over 2}]]. These two chains thus form the second major motif, also shown in Fig. 2[link], namely an R64(16) ring. There is thus an alternating ladder of these two motifs, which combine to give the corrugated sheets.

The nitro O atoms do not participate in the strong hydrogen bonding described above. The only likely connection is through a very weak aryl C5—H5⋯O4iii bond [symmetry code: (iii) x + 1, y, z], which would contribute to the sheet structure, forming chains along [100].

[Figure 1]
Figure 1
The mol­ecular structure of (I)[link], showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
[Figure 2]
Figure 2
Part of the unit cell of (I)[link], showing the formation of hydrogen-bonded rings. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. Atoms labelled with (i), (ii) or a hash (#) are at the symmetry positions (x − [{1\over 2}], −y + [{1\over 2}], z − [{1\over 2}]), (x − [{1\over 2}], −y + [{1\over 2}], z + [{1\over 2}]) and (x − 1, y, z), respectively.
[Figure 3]
Figure 3
NOT USED [Please provide caption]

Experimental

Solutions of aminoguanidinium carbonate, [HN=C(NH2)—NH—NH2]·H2CO3 (3 mmol), in MeOH (20 ml) and 2-nitro­benzoic acid (3 mmol) in MeOH (20 ml) were mixed. After the effervescence had subsided, the reaction solution was maintained at 313 K for 30 min, left overnight at room temperature and then reduced on a rotary evaporator to leave crude [(H2N)2C—NH—NH2]+·[2-O2NC6H4CO2]−. Attempts to obtain suitable crystals of [(H2N)2C—NH—NH2]+·[2-O2NC6H4CO2]− for X-ray study from EtOH and MeOH solutions failed. The crude material was dissolved in acetone, and the solution was left to produce crystals of (I)[link] slowly (m.p. 449–451 K).

Crystal data

  • C4H11N4+·C7H4NO4−

  • Mr = 281.28

  • Monoclinic, P 21 /n

  • a = 7.8683 (4) Å

  • b = 19.4979 (12) Å

  • c = 9.1273 (5) Å

  • β = 98.968 (3)°

  • V = 1383.15 (13) Å3

  • Z = 4

  • Dx = 1.351 Mg m−3

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 120 (2) K

  • Cut plate, colourless

  • 0.28 × 0.12 × 0.02 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • φ and ω scans

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.]) Tmin = 0.623, Tmax = 0.928 (expected range = 0.670–0.998)

  • 18434 measured reflections

  • 3163 independent reflections

  • 2158 reflections with I > 2σ(I)

  • Rint = 0.087

  • θmax = 27.5°
Refinement

  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.133

  • S = 1.06

  • 3163 reflections

  • 183 parameters

  • H-atom parameters constrained

  • w = 1/[σ2(Fo2) + (0.044P)2 + 0.8011P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯O1 0.88 2.04 2.912 (2) 174
N3—H3A⋯O2 0.88 1.90 2.774 (2) 175
N2—H2B⋯O2i 0.88 2.12 2.926 (2) 152
N3—H3B⋯O1ii 0.88 2.22 2.994 (2) 146
N4—H4A⋯O1ii 0.88 2.06 2.863 (2) 151
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 (aryl) or 0.98 Å (methyl) and N—H distances of 0.88 Å, with Uiso(H) values of 1.2Ueq(aryl or NH) or 1.5Ueq(methyl). The displacement ellipsoid for nitro atom O3 was large, with a high U33 value. Attempts to split the position of O3 over two sites were unsuccessful, simply leading to one dominant large ellipsoid, and one even larger ellipsoid with very low occupancy. Hence, despite the large value obtained, the single-site model was retained for the final refinement.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003[McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.]) and SHELXS97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: CIFTAB (Sheldrick, 1997b[Sheldrick, G. M. (1997b). CIFTAB. University of Göttingen, Germany.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270106020580/fg3021sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106020580/fg3021Isup2.hkl


Comment top

Some of us have previously reported the supramolecular arrangements of anilinium salts of arenecarboxylates (e.g. Glidewell et al., 2003, 2005a,b). We now report the structure and supramolecular arrangement of the title compound, [(H2N)2C—NH—N=CMe2]+.[2-O2NC6H4CO2]−, (I).

The crystal structure solution confirms the presence of a salt composed of a 2-nitrobenzoate anion and an [(H2N)2CNH—N═CMe2]+ cation. The adjacent positions of the carboxy and nitro groups in the nitrobenzoate anion lead to both groups twisting away from the plane; the latter is twisted at an angle of 24.72 (15)°, whereas the carboxy group is more nearly perpendicular, at 71.18°, as can be seen in Fig. 1. The 1-methylethyliminoguanidinium complex is nearly planar, with an r.m.s. deviation of 0.0635 Å, and atom N4 shows the largest deviation from planarity [0.1256 (16) Å]. The angle between the plane defined by this molecule and that of the 2-nitrobenzoate ring is 72.17 (7)°. A complex strong hydrogen-bonding scheme operates between the cation and the anion (Table 1). The N atoms in guanidine act as donors, with the carboxy O atoms in nitrobenzoate the acceptors.

Two main motifs dominate the hydrogen bonding in (I). Firstly, a nearly symmetrical simple R22(8) ring (Bernstein et al., 1995) forms from hydrogen bonding between the two molecules, involving the two guanidine amino groups and the two carboxy O atoms, N2—H2A···O1 and N3—H3A···O2 (Fig. 1). These simple dimeric rings are linked by the other hydrogen bonds to form corrugated sheets (Fig. 2).

The carboxy O atoms are central to the hydrogen-bonding scheme, and both act as multiple acceptors. As well as acting as an acceptor in the dimer described above, carboxy atom O1 acts as a double acceptor to other guanadine donors, N3—H3B···O1ii and N4—H4A···O1ii [symmetry code: (ii) x − 1/2, −y + 1/2, z + 1/2]. The other carboxy atom, O2, also is an acceptor for the guanadine donor, N2—H2B···O2i [symmetry code: (i) x − 1/2, −y + 1/2, z − 1/2]. These two chains thus form the second major motif, also shown in Fig. 2, an R46(16) ring. There is thus an alternating ladder of these two motifs, which combine to give the corrugated sheets.

The nitro O atoms do not participate in the strong hydrogen bonding described above (Fig. 3). The only likely connection is through a very weak aryl C5—H5···O4iii bond [symmetry code: (iii) x + 1, y, z], which would contribute to the sheet structure, forming chains along [100].

Experimental top

Solutions of aminoquanidinium carbonate, [HN═ C(NH2)—NH—NH2]·H2CO3 (3 mmol), in MeOH (20 ml) and 2-nitrobenzoic acid (3 mmol) in MeOH (20 ml) were mixed. After the effervescence had subsided, the reaction solution was maintained at 313 K for 30 min, left overnight at room temperature and then reduced on a rotary evaporator to leave crude [(H2N)2C—NH—NH2]+.[2-O2NC6H4CO2]−. Attempts to obtain suitable crystals of [(H2N)2C—NH—NH2]+.[2-O2NC6H4CO2]− for X-ray study from EtOH and MeOH solutions failed. The crude material was dissolved in acetone, and the solution was left to produce slowly crystals of [(H2N)2C—NH—N═CMe2]+.[2-O2NC6H4CO2]−, (I) (m.p. 449–451 K).

Refinement top

All H atoms were located in difference maps and then treated as riding atoms, with C—H distances of 0.95 (aryl) and 0.98 (methyl) and N—H distances of 0.88 Å, with Uiso(H) values of 1.2Ueq(aryl, N—H) or 1.5Ueq(methyl). The displacement ellipsoid for the nitro atom O3 is large, with a high U33 value. Attempts to split the position of O3 over two sites were unsuccessful, simply leading to one dominant large ellipsoid and one even larger ellipsoid, with very low occupancy at the latter site. Hence, despite the large value obtained, the single-site model was retained for the final refinement.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. Part of the unit cell of (I), showing the formation of hydrogen-bonded rings. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds. Atoms labelled with (i), (ii) or a hash (#) are at the symmetry positions (x − 1/2, −y + 1/2, z − 1/2), (x − 1/2, −y + 1/2, z + 1/2) and (x − 1, y, z), respectively.
[Figure 3] Fig. 3. [Please provide caption]
1-(Isopropylideneamino)guanidinium 2-nitrobenzoate top
Crystal data top
C4H11N4+·C7H4NO4−F(000) = 592
Mr = 281.28Dx = 1.351 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3213 reflections
a = 7.8683 (4) Åθ = 2.9–27.5°
b = 19.4979 (12) ŵ = 0.11 mm−1
c = 9.1273 (5) ÅT = 120 K
β = 98.968 (3)°Cut plate, colourless
V = 1383.15 (13) Å30.28 × 0.12 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer		3163 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2158 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		k = −24→25
Tmin = 0.623, Tmax = 0.928l = −11→11
18434 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: difference Fourier map
wR(F2) = 0.133H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.044P)2 + 0.8011P]
where P = (Fo2 + 2Fc2)/3
3163 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C4H11N4+·C7H4NO4−V = 1383.15 (13) Å3
Mr = 281.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.8683 (4) ŵ = 0.11 mm−1
b = 19.4979 (12) ÅT = 120 K
c = 9.1273 (5) Å0.28 × 0.12 × 0.02 mm
β = 98.968 (3)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		3163 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2158 reflections with I > 2σ(I)
Tmin = 0.623, Tmax = 0.928Rint = 0.087
18434 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.06Δρmax = 0.23 e Å−3
3163 reflectionsΔρmin = −0.32 e Å−3
183 parameters
Special details top

Experimental. IR: 3300–2300 (br), 1687, 1611, 1585, 1527, 1477, 1431, 1380, 1353, 1275, 1121, 1075, 1048, 1002, 861, 833, 788, 750, 701, 650, 604, 476, 426 cm−1.

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 (Å2) top
xyzUiso*/Ueq
C11.0366 (2)0.12430 (11)0.1802 (2)0.0218 (5)
C21.0220 (3)0.05393 (12)0.1860 (3)0.0316 (5)
C31.1579 (3)0.00965 (13)0.1781 (3)0.0423 (7)
H31.1423−0.03860.18290.051*
C41.3158 (3)0.03669 (12)0.1632 (3)0.0351 (6)
H41.41060.00720.15700.042*
C51.3355 (3)0.10675 (11)0.1575 (2)0.0253 (5)
H51.44460.12560.14790.030*
C61.1981 (2)0.14973 (11)0.1655 (2)0.0234 (5)
H61.21430.19790.16100.028*
C70.8960 (2)0.17504 (11)0.1997 (2)0.0219 (5)
O10.83577 (17)0.21158 (8)0.08948 (16)0.0265 (4)
O20.85737 (18)0.17948 (8)0.32661 (16)0.0303 (4)
N10.8540 (2)0.02249 (11)0.1982 (3)0.0470 (6)
O30.8524 (2)−0.03541 (11)0.2475 (3)0.0903 (9)
O40.72454 (19)0.05567 (9)0.1554 (2)0.0440 (5)
N20.5284 (2)0.28867 (9)0.12689 (19)0.0254 (4)
H2A0.62380.26790.11270.030*
H2B0.46630.31090.05340.030*
C80.4785 (2)0.28645 (10)0.2581 (2)0.0210 (4)
N30.5685 (2)0.25358 (9)0.37024 (19)0.0264 (4)
H3A0.66430.23250.35850.032*
H3B0.53290.25270.45700.032*
N40.3308 (2)0.31656 (9)0.28102 (19)0.0224 (4)
H4A0.30130.31780.37010.027*
N50.2264 (2)0.34559 (9)0.16045 (18)0.0239 (4)
C90.0769 (3)0.36564 (10)0.1821 (2)0.0235 (5)
C10−0.0340 (3)0.39763 (13)0.0523 (3)0.0365 (6)
H10A0.02950.3998−0.03180.055*
H10B−0.06610.44410.07850.055*
H10C−0.13810.37000.02510.055*
C110.0074 (3)0.35807 (12)0.3249 (2)0.0301 (5)
H11A−0.10440.38100.31660.045*
H11B0.08760.37890.40550.045*
H11C−0.00630.30930.34600.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0207 (10)0.0261 (12)0.0188 (10)0.0017 (8)0.0041 (8)−0.0002 (8)
C20.0175 (10)0.0305 (13)0.0465 (15)−0.0024 (9)0.0036 (10)0.0049 (11)
C30.0270 (12)0.0248 (13)0.0731 (19)0.0006 (9)0.0012 (12)0.0045 (12)
C40.0236 (11)0.0309 (13)0.0503 (15)0.0048 (9)0.0044 (11)−0.0039 (11)
C50.0188 (10)0.0314 (12)0.0264 (11)−0.0012 (9)0.0053 (9)−0.0003 (9)
C60.0227 (10)0.0239 (11)0.0237 (11)−0.0026 (8)0.0038 (9)−0.0011 (9)
C70.0200 (10)0.0249 (11)0.0212 (11)−0.0020 (8)0.0048 (8)−0.0018 (9)
O10.0257 (8)0.0326 (9)0.0220 (8)0.0067 (6)0.0057 (6)0.0025 (7)
O20.0290 (8)0.0422 (10)0.0205 (8)0.0090 (7)0.0066 (6)0.0002 (7)
N10.0244 (11)0.0351 (13)0.0814 (17)−0.0037 (9)0.0080 (11)0.0124 (12)
O30.0391 (11)0.0496 (13)0.182 (3)−0.0072 (9)0.0154 (14)0.0521 (16)
O40.0197 (8)0.0432 (11)0.0688 (13)0.0008 (7)0.0065 (8)0.0004 (9)
N20.0233 (9)0.0328 (11)0.0210 (9)0.0062 (7)0.0065 (7)0.0011 (8)
C80.0197 (10)0.0222 (11)0.0218 (11)−0.0021 (8)0.0049 (8)−0.0026 (9)
N30.0233 (9)0.0343 (11)0.0226 (10)0.0063 (8)0.0063 (8)0.0013 (8)
N40.0223 (9)0.0279 (10)0.0179 (8)0.0035 (7)0.0058 (7)0.0005 (7)
N50.0253 (9)0.0236 (10)0.0226 (9)0.0020 (7)0.0027 (7)0.0002 (8)
C90.0236 (11)0.0226 (11)0.0242 (11)0.0018 (8)0.0038 (9)−0.0012 (9)
C100.0357 (13)0.0412 (15)0.0318 (13)0.0096 (11)0.0024 (10)0.0009 (11)
C110.0254 (11)0.0319 (13)0.0342 (13)0.0045 (9)0.0083 (10)0.0004 (10)
Geometric parameters (Å, º) top
C1—C21.379 (3)N2—H2A0.8800
C1—C61.390 (3)N2—H2B0.8800
C1—C71.515 (3)C8—N31.317 (3)
C2—C31.385 (3)C8—N41.347 (2)
C2—N11.477 (3)N3—H3A0.8800
C3—C41.376 (3)N3—H3B0.8800
C3—H30.9500N4—N51.387 (2)
C4—C51.377 (3)N4—H4A0.8800
C4—H40.9500N5—C91.284 (3)
C5—C61.379 (3)C9—C101.494 (3)
C5—H50.9500C9—C111.497 (3)
C6—H60.9500C10—H10A0.9800
C7—O21.246 (2)C10—H10B0.9800
C7—O11.263 (2)C10—H10C0.9800
N1—O31.216 (3)C11—H11A0.9800
N1—O41.219 (2)C11—H11B0.9800
N2—C81.318 (3)C11—H11C0.9800
C2—C1—C6116.22 (18)H2A—N2—H2B120.0
C2—C1—C7125.32 (17)N3—C8—N2121.47 (17)
C6—C1—C7118.29 (18)N3—C8—N4117.63 (18)
C1—C2—C3123.28 (19)N2—C8—N4120.87 (18)
C1—C2—N1119.81 (19)C8—N3—H3A120.0
C3—C2—N1116.9 (2)C8—N3—H3B120.0
C4—C3—C2118.9 (2)H3A—N3—H3B120.0
C4—C3—H3120.6C8—N4—N5118.23 (16)
C2—C3—H3120.6C8—N4—H4A120.9
C3—C4—C5119.5 (2)N5—N4—H4A120.9
C3—C4—H4120.2C9—N5—N4116.44 (17)
C5—C4—H4120.2N5—C9—C10116.15 (19)
C4—C5—C6120.45 (19)N5—C9—C11124.88 (19)
C4—C5—H5119.8C10—C9—C11118.97 (18)
C6—C5—H5119.8C9—C10—H10A109.5
C5—C6—C1121.6 (2)C9—C10—H10B109.5
C5—C6—H6119.2H10A—C10—H10B109.5
C1—C6—H6119.2C9—C10—H10C109.5
O2—C7—O1125.87 (18)H10A—C10—H10C109.5
O2—C7—C1116.29 (18)H10B—C10—H10C109.5
O1—C7—C1117.70 (17)C9—C11—H11A109.5
O3—N1—O4123.7 (2)C9—C11—H11B109.5
O3—N1—C2118.31 (19)H11A—C11—H11B109.5
O4—N1—C2118.0 (2)C9—C11—H11C109.5
C8—N2—H2A120.0H11A—C11—H11C109.5
C8—N2—H2B120.0H11B—C11—H11C109.5
C6—C1—C2—C30.0 (3)C6—C1—C7—O2−105.7 (2)
C7—C1—C2—C3−175.2 (2)C2—C1—C7—O1−114.6 (2)
C6—C1—C2—N1−178.7 (2)C6—C1—C7—O170.3 (2)
C7—C1—C2—N16.1 (3)C1—C2—N1—O3−158.1 (3)
C1—C2—C3—C4−0.2 (4)C3—C2—N1—O323.2 (4)
N1—C2—C3—C4178.5 (2)C1—C2—N1—O423.4 (4)
C2—C3—C4—C50.4 (4)C3—C2—N1—O4−155.3 (2)
C3—C4—C5—C6−0.4 (4)N3—C8—N4—N5−173.85 (18)
C4—C5—C6—C10.2 (3)N2—C8—N4—N54.6 (3)
C2—C1—C6—C50.0 (3)C8—N4—N5—C9171.07 (18)
C7—C1—C6—C5175.55 (18)N4—N5—C9—C10179.29 (18)
C2—C1—C7—O269.4 (3)N4—N5—C9—C11−1.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.882.042.912 (2)174
N3—H3A···O20.881.902.774 (2)175
N2—H2B···O2i0.882.122.926 (2)152
N3—H3B···O1ii0.882.222.994 (2)146
N4—H4A···O1ii0.882.062.863 (2)151
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC4H11N4+·C7H4NO4−
Mr281.28
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)7.8683 (4), 19.4979 (12), 9.1273 (5)
β (°) 98.968 (3)
V (Å3)1383.15 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.28 × 0.12 × 0.02
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.623, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections		18434, 3163, 2158
Rint0.087
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.133, 1.06
No. of reflections3163
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.23, −0.32

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997a), OSCAIL and SHELXL97 (Sheldrick, 1997a), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.882.042.912 (2)174.4
N3—H3A···O20.881.902.774 (2)174.5
N2—H2B···O2i0.882.122.926 (2)151.5
N3—H3B···O1ii0.882.222.994 (2)146.2
N4—H4A···O1ii0.882.062.863 (2)151.3
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.
 

Acknowledgements

We are indebted to the EPSRC for the use of both the Chemical Database Service at Daresbury, primarily for access to the Cambridge Structural Database (Fletcher et al., 1996[Fletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746-749.]), and the EPSRC National Crystallography Service at the University of Southampton, for data collection.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746–749.  CrossRef CAS Web of Science Google Scholar
 First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o509–o511.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005a). Acta Cryst. C61, o246–o248.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationGlidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005b). Acta Cryst. C61, o276–o280.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMcArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland.  Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (1997b). CIFTAB. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany.  Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Volume 62| Part 8| August 2006| Pages o476-o477
doi:10.1107/S0108270106020580
Follow Acta Cryst. C
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS