![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
Bis(propane-1,2-diammonium) benzene-1,2,4,5-tetracarboxylate dihydrate
aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: majdolashrafi.m@gmail.com
In the crystal of the title hydrated molecular salt, 2C3H12N22+·C10H2O84−·2H2O, the packing is stabilized by extensive N—H⋯O and O—H⋯O hydrogen-bonding interactions involving all three species, forming a supramolecular three-dimensional structure. The tetraanion is generated by inversion.
Related literature
For proton transfer systems, see: Aghabozorg et al. (2008); Arora & Pedireddi (2003
). For related structures, see: Wang et al. (2005
); Ma et al. (2005
); Mrvos-Sermek et al. (1996
); Rafizadeh et al. (2006
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007
); data reduction: SHELXTL (Sheldrick, 2008
); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1999
); software used to prepare material for publication: WinGX (Farrugia, 1999
).
Supporting information
https://doi.org/10.1107/S1600536810044065/jj2064sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044065/jj2064Isup2.hkl
Propane-1,2-diamine (12.6 mmol) was added to a solution of benzene-1,2,4,5-tetracarboxylic acid (1.65 g, 6.3 mmol) in ethanol (30 ml) at room temperature. The milky precipitated product was recrystallized from water. After one week, colorless plate crystals of (I) were isolated (yield 87.1%, decomposition < 420 K)
All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93, 0.98Å (CH), 0.97Å (CH2) 0.96Å (CH3) or 0.89Å (NH). Isotropic displacement parameters for these atoms were set to 1.5 times (NH), 1.2 (CH, CH2, CH3) times Ueq of the parent atom. Water H atoms atoms were located in a difference Fourier map and refined isotropically without restraint.
Several proton transfer systems using benzene- 1,2,4,5-tetracarboxylic acid (H4BTC), with nitrogen donor molecules, such as 1,10-phenanthroline, 1,7-phenanthroline, phenazine, 4-(N,N-dimethylamino)pyridine, 1,2-bis(4-pyridyl) ethene and 1,2-bis(4-pyridyl)ethane, have been synthesized and characterized by X-ray diffraction methods (Aghabozorg et al. 2008, Arora & Pedireddi, 2003). R%elated crystal structures of (H2BTC)(Hphen)2- (H4BTC) (where phen is 1,10-phenanthroline; Wang et al., 2005), (H3BTC)(Hbipy).3H2O (where bipy is 2,20-bipyridine; Ma et al., 2005), (H2BTC)(Hbipy)2(H4BTC) (Mrvos-Sermek et al., 1996) and (BTC)(H2en)2.2H2O (Rafizadeh et al. 2006) have been reported previously.
In the title compound, (C3H12N2)22+ (C10H2O8)4-. 2H2O, the
contains two diprotonated propane-1,2-diamine cations, one tetraanionic deprotonated anion form of benzene-1,2,4,5-tetracarboxylic acid and two water molecules (Fig. 1). The dication forms from the transfer of a single proton from each of the carboxyl groups to a propane-1,2-diamine molecule. The negative charges of one of the tetraanionic 1,2,4,5-benzenetetracarboxylate groups, is thereby neutralized by a doubly protonated propane-1,2-diammonium fragment. Crystal packing is stabilized by extensive N—H···O and O—H···O hydrogen bonding interactions involving all three species forming a supramolecular 3-D structure (Fig. 2).For proton transfer systems, see: Aghabozorg et al. (2008); Arora & Pedireddi, (2003). For related structures, see: Wang et al. (2005); Ma et al. (2005); Mrvos-Sermek et al. (1996); Rafizadeh et al. (2006).
Data collection: SMART (Bruker, 2007); cell
SMART (Bruker, 2007); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).2C3H12N22+·C10H2O84−·2H2O | F(000) = 468 |
Mr = 438.44 | Dx = 1.441 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8157 reflections |
a = 10.427 (2) Å | θ = 2.3–30.5° |
b = 7.6955 (15) Å | µ = 0.12 mm−1 |
c = 12.854 (3) Å | T = 298 K |
β = 101.61 (3)° | Plate, colorless |
V = 1010.3 (3) Å3 | 0.49 × 0.40 × 0.08 mm |
Z = 2 |
Bruker SMART CD area-detector diffractometer | 3038 independent reflections |
Radiation source: fine-focus sealed tube | 2727 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 30.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −14→14 |
Tmin = 0.940, Tmax = 0.990 | k = −10→10 |
8157 measured reflections | l = −15→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.3092P] where P = (Fo2 + 2Fc2)/3 |
3038 reflections | (Δ/σ)max = 0.004 |
146 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
2C3H12N22+·C10H2O84−·2H2O | V = 1010.3 (3) Å3 |
Mr = 438.44 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.427 (2) Å | µ = 0.12 mm−1 |
b = 7.6955 (15) Å | T = 298 K |
c = 12.854 (3) Å | 0.49 × 0.40 × 0.08 mm |
β = 101.61 (3)° |
Bruker SMART CD area-detector diffractometer | 3038 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | 2727 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.990 | Rint = 0.026 |
8157 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.39 e Å−3 |
3038 reflections | Δρmin = −0.19 e Å−3 |
146 parameters |
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 | 0.25868 (9) | 0.83996 (13) | 1.05876 (8) | 0.01914 (19) | |
C2 | 0.12279 (9) | 0.91697 (12) | 1.02583 (7) | 0.01626 (18) | |
C3 | 0.06315 (9) | 0.94408 (12) | 0.91926 (7) | 0.01595 (17) | |
C4 | 0.12422 (9) | 0.88991 (13) | 0.82686 (7) | 0.01717 (18) | |
C5 | −0.05822 (9) | 1.02713 (13) | 0.89486 (7) | 0.01784 (18) | |
H5 | −0.0971 | 1.0457 | 0.8240 | 0.021* | |
C6 | 0.39782 (14) | 0.3316 (2) | 1.09027 (10) | 0.0389 (3) | |
H6A | 0.3587 | 0.2308 | 1.1150 | 0.047* | |
H6B | 0.3728 | 0.4332 | 1.1246 | 0.047* | |
H6C | 0.4914 | 0.3200 | 1.1067 | 0.047* | |
C7 | 0.35129 (11) | 0.34862 (15) | 0.97084 (9) | 0.0245 (2) | |
H7 | 0.3899 | 0.4541 | 0.9475 | 0.029* | |
C8 | 0.20338 (10) | 0.36693 (14) | 0.94363 (9) | 0.0241 (2) | |
H8A | 0.1645 | 0.2735 | 0.9774 | 0.029* | |
H8B | 0.1789 | 0.4758 | 0.9723 | 0.029* | |
N1 | 0.39794 (8) | 0.19628 (13) | 0.91649 (7) | 0.02395 (19) | |
H1A | 0.3594 | 0.1001 | 0.9333 | 0.036* | |
H1B | 0.4843 | 0.1861 | 0.9373 | 0.036* | |
H1C | 0.3779 | 0.2120 | 0.8465 | 0.036* | |
N2 | 0.14955 (9) | 0.36274 (12) | 0.82766 (7) | 0.02209 (18) | |
H2A | 0.1997 | 0.4268 | 0.7942 | 0.033* | |
H2B | 0.0685 | 0.4053 | 0.8147 | 0.033* | |
H2C | 0.1481 | 0.2536 | 0.8046 | 0.033* | |
O1 | 0.28549 (8) | 0.75595 (13) | 1.14363 (7) | 0.0344 (2) | |
O2 | 0.33872 (7) | 0.87232 (12) | 0.99958 (7) | 0.0302 (2) | |
O3 | 0.12767 (9) | 0.73323 (10) | 0.80446 (7) | 0.02951 (19) | |
O4 | 0.16276 (8) | 1.01227 (10) | 0.77470 (6) | 0.02490 (18) | |
OW1 | 0.89422 (11) | 0.47495 (18) | 0.80452 (13) | 0.0566 (4) | |
H1W | 0.833 (2) | 0.408 (3) | 0.8154 (16) | 0.052 (5)* | |
H2W | 0.869 (2) | 0.559 (3) | 0.769 (2) | 0.065 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0145 (4) | 0.0196 (4) | 0.0234 (4) | 0.0020 (3) | 0.0040 (3) | 0.0006 (3) |
C2 | 0.0141 (4) | 0.0176 (4) | 0.0179 (4) | 0.0015 (3) | 0.0053 (3) | 0.0012 (3) |
C3 | 0.0154 (4) | 0.0171 (4) | 0.0167 (4) | 0.0003 (3) | 0.0067 (3) | −0.0010 (3) |
C4 | 0.0160 (4) | 0.0199 (4) | 0.0167 (4) | 0.0015 (3) | 0.0059 (3) | −0.0016 (3) |
C5 | 0.0161 (4) | 0.0230 (4) | 0.0148 (4) | 0.0020 (3) | 0.0040 (3) | 0.0008 (3) |
C6 | 0.0414 (7) | 0.0510 (8) | 0.0217 (5) | −0.0021 (6) | 0.0002 (5) | −0.0028 (5) |
C7 | 0.0240 (5) | 0.0262 (5) | 0.0229 (5) | −0.0040 (4) | 0.0038 (4) | −0.0001 (4) |
C8 | 0.0241 (5) | 0.0253 (5) | 0.0243 (5) | 0.0013 (4) | 0.0086 (4) | −0.0007 (4) |
N1 | 0.0187 (4) | 0.0302 (5) | 0.0234 (4) | 0.0020 (3) | 0.0052 (3) | 0.0036 (3) |
N2 | 0.0202 (4) | 0.0208 (4) | 0.0257 (4) | 0.0013 (3) | 0.0058 (3) | 0.0023 (3) |
O1 | 0.0243 (4) | 0.0431 (5) | 0.0355 (5) | 0.0087 (3) | 0.0055 (3) | 0.0183 (4) |
O2 | 0.0167 (3) | 0.0416 (5) | 0.0345 (4) | 0.0056 (3) | 0.0107 (3) | 0.0097 (4) |
O3 | 0.0440 (5) | 0.0192 (4) | 0.0302 (4) | −0.0002 (3) | 0.0189 (3) | −0.0043 (3) |
O4 | 0.0322 (4) | 0.0211 (4) | 0.0262 (4) | −0.0002 (3) | 0.0174 (3) | 0.0001 (3) |
OW1 | 0.0266 (5) | 0.0496 (7) | 0.0948 (10) | 0.0052 (5) | 0.0151 (5) | 0.0303 (7) |
O1—C1 | 1.2504 (14) | C1—C2 | 1.5155 (14) |
O2—C1 | 1.2620 (13) | C2—C5i | 1.3978 (13) |
O3—C4 | 1.2418 (13) | C2—C3 | 1.4014 (13) |
O4—C4 | 1.2673 (13) | C3—C5 | 1.3959 (14) |
OW1—H1W | 0.85 (2) | C3—C4 | 1.5147 (13) |
OW1—H2W | 0.81 (2) | C5—H5 | 0.9300 |
N1—C7 | 1.4953 (15) | C6—C7 | 1.5197 (17) |
N2—C8 | 1.4837 (15) | C7—C8 | 1.5178 (16) |
N1—H1B | 0.8900 | C6—H6B | 0.9600 |
N1—H1C | 0.8900 | C6—H6C | 0.9600 |
N1—H1A | 0.8900 | C6—H6A | 0.9600 |
N2—H2C | 0.8900 | C7—H7 | 0.9800 |
N2—H2B | 0.8900 | C8—H8B | 0.9700 |
N2—H2A | 0.8900 | C8—H8A | 0.9700 |
O1···OW1ii | 2.7596 (17) | C3···H8Avi | 2.7900 |
O1···OW1iii | 2.9845 (19) | C4···H2Cvi | 2.8300 |
OW1···O1iv | 2.9845 (19) | C4···H1Avi | 3.0300 |
OW1···O3v | 3.1427 (17) | C4···H2Aix | 2.6500 |
OW1···N2v | 2.7574 (17) | C4···H1Cix | 2.6100 |
OW1···O1ii | 2.7596 (17) | C5···H8Avi | 3.0200 |
O2···C4 | 2.8198 (14) | C6···H7ii | 2.8800 |
O2···O3 | 3.1713 (14) | C7···H7ii | 3.0900 |
O2···N1vi | 2.8289 (15) | H1W···H2Bv | 2.4600 |
O2···N1ii | 2.7910 (13) | H1W···O1ii | 1.91 (2) |
O3···C8 | 3.3468 (16) | H1W···C1ii | 2.79 (2) |
O3···O2 | 3.1713 (14) | H1A···C4xii | 3.0300 |
O3···C1 | 3.3806 (16) | H1A···O2xii | 1.9800 |
O3···N2 | 2.8710 (14) | H1A···H6A | 2.5400 |
O3···OW1vii | 3.1427 (17) | H1A···H8A | 2.5900 |
O3···O4viii | 3.0979 (14) | H1A···C1xii | 2.9000 |
O3···N1ix | 2.8130 (14) | H1A···O4xii | 2.6700 |
O4···N2vi | 2.7918 (14) | H1B···O1ii | 2.8400 |
O4···N2ix | 2.8146 (14) | H1B···C1ii | 2.6800 |
O4···N1vi | 3.0889 (14) | H1B···O2ii | 1.9100 |
O4···C7ix | 3.3738 (16) | H1B···H6C | 2.4000 |
O4···O3ix | 3.0979 (14) | H1C···O4xii | 2.7200 |
O1···H1Bii | 2.8400 | H1C···C4viii | 2.6100 |
O1···H6B | 2.6700 | H1C···O3viii | 1.9400 |
O1···H5i | 2.5900 | H1C···O4viii | 2.7700 |
O1···H2Wiii | 2.20 (2) | H1C···H2A | 2.4800 |
O1···H1Wii | 1.91 (2) | H1C···H2C | 2.3700 |
OW1···H6Ax | 2.8700 | H1C···N2 | 2.6200 |
OW1···H2Bv | 1.8700 | H2W···C1iv | 2.83 (2) |
O2···H1Avi | 1.9800 | H2W···H2Bv | 2.3600 |
O2···H6Cii | 2.8600 | H2W···O1iv | 2.20 (2) |
O2···H1Bii | 1.9100 | H2A···O4viii | 1.9500 |
O3···H8B | 2.9000 | H2A···N1 | 2.9300 |
O3···H2Aix | 2.8300 | H2A···O3 | 2.4900 |
O3···H1Cix | 1.9400 | H2A···C4viii | 2.6500 |
O3···H2A | 2.4900 | H2A···O3viii | 2.8300 |
O3···H2B | 2.6100 | H2A···H1C | 2.4800 |
O4···H2Aix | 1.9500 | H2A···H7 | 2.5100 |
O4···H1Cix | 2.7700 | H2B···O3 | 2.6100 |
O4···H5 | 2.9200 | H2B···H2Wvii | 2.3600 |
O4···H7ix | 2.8300 | H2B···OW1vii | 1.8700 |
O4···H6Cxi | 2.8200 | H2B···H1Wvii | 2.4600 |
O4···H2Cvi | 1.9100 | H2C···C3xii | 3.0300 |
O4···H1Avi | 2.6700 | H2C···N1 | 2.7500 |
O4···H1Cvi | 2.7200 | H2C···H1C | 2.3700 |
N1···N2 | 2.9090 (15) | H2C···O4xii | 1.9100 |
N1···O2xii | 2.8289 (15) | H2C···C4xii | 2.8300 |
N1···O4xii | 3.0889 (14) | H5···O1i | 2.5900 |
N1···C4viii | 3.4304 (15) | H5···H6Bxi | 2.5200 |
N1···O2ii | 2.7910 (13) | H5···O4 | 2.9200 |
N1···O3viii | 2.8130 (14) | H6A···OW1xiii | 2.8700 |
N2···O4viii | 2.8146 (14) | H6A···H1A | 2.5400 |
N2···O3 | 2.8710 (14) | H6A···H8A | 2.4300 |
N2···O4xii | 2.7918 (14) | H6B···H5xiv | 2.5200 |
N2···N1 | 2.9090 (15) | H6B···H8B | 2.5400 |
N2···C4viii | 3.3822 (15) | H6B···O1 | 2.6700 |
N2···OW1vii | 2.7574 (17) | H6C···O2ii | 2.8600 |
N1···H2C | 2.7500 | H6C···H7ii | 2.3200 |
N1···H2A | 2.9300 | H6C···H1B | 2.4000 |
N2···H1C | 2.6200 | H6C···O4xiv | 2.8200 |
C1···O3 | 3.3806 (16) | H7···H6Cii | 2.3200 |
C3···C8vi | 3.5554 (16) | H7···H7ii | 2.5200 |
C4···N1ix | 3.4304 (15) | H7···C7ii | 3.0900 |
C4···O2 | 2.8198 (14) | H7···H2A | 2.5100 |
C4···N2ix | 3.3822 (15) | H7···O4viii | 2.8300 |
C7···O4viii | 3.3738 (16) | H7···C6ii | 2.8800 |
C8···O3 | 3.3468 (16) | H8A···H6A | 2.4300 |
C8···C3xii | 3.5554 (16) | H8A···C3xii | 2.7900 |
C1···H1Bii | 2.6800 | H8A···C5xii | 3.0200 |
C1···H2Wiii | 2.83 (2) | H8A···C2xii | 2.8700 |
C1···H1Avi | 2.9000 | H8A···H1A | 2.5900 |
C1···H8B | 3.0700 | H8B···C1 | 3.0700 |
C1···H1Wii | 2.79 (2) | H8B···H6B | 2.5400 |
C2···H8Avi | 2.8700 | H8B···O3 | 2.9000 |
C3···H2Cvi | 3.0300 | ||
H1W—OW1—H2W | 114 (2) | O3—C4—O4 | 124.87 (10) |
H1A—N1—H1C | 109.00 | O4—C4—C3 | 116.01 (9) |
H1B—N1—H1C | 109.00 | C2i—C5—C3 | 121.67 (9) |
C7—N1—H1C | 109.00 | C3—C5—H5 | 119.00 |
C7—N1—H1A | 109.00 | C2i—C5—H5 | 119.00 |
C7—N1—H1B | 109.00 | C6—C7—C8 | 110.11 (10) |
H1A—N1—H1B | 109.00 | N1—C7—C6 | 109.67 (10) |
C8—N2—H2A | 109.00 | N1—C7—C8 | 112.09 (9) |
H2A—N2—H2C | 110.00 | N2—C8—C7 | 113.01 (9) |
C8—N2—H2C | 109.00 | C7—C6—H6B | 109.00 |
H2A—N2—H2B | 109.00 | C7—C6—H6C | 110.00 |
C8—N2—H2B | 109.00 | H6A—C6—H6B | 109.00 |
H2B—N2—H2C | 109.00 | H6A—C6—H6C | 109.00 |
O2—C1—C2 | 116.68 (9) | H6B—C6—H6C | 109.00 |
O1—C1—O2 | 124.68 (10) | C7—C6—H6A | 109.00 |
O1—C1—C2 | 118.57 (9) | N1—C7—H7 | 108.00 |
C1—C2—C3 | 122.50 (9) | C8—C7—H7 | 108.00 |
C3—C2—C5i | 118.88 (9) | C6—C7—H7 | 108.00 |
C1—C2—C5i | 118.50 (9) | N2—C8—H8A | 109.00 |
C2—C3—C4 | 123.48 (9) | N2—C8—H8B | 109.00 |
C2—C3—C5 | 119.45 (9) | C7—C8—H8B | 109.00 |
C4—C3—C5 | 117.07 (8) | H8A—C8—H8B | 108.00 |
O3—C4—C3 | 119.04 (9) | C7—C8—H8A | 109.00 |
O1—C1—C2—C5i | 32.71 (14) | C5i—C2—C3—C5 | 0.53 (14) |
O2—C1—C2—C3 | 31.49 (14) | C5—C3—C4—O3 | −107.87 (11) |
O1—C1—C2—C3 | −151.38 (10) | C4—C3—C5—C2i | −179.74 (9) |
O2—C1—C2—C5i | −144.42 (10) | C5—C3—C4—O4 | 68.84 (12) |
C1—C2—C3—C4 | 3.77 (15) | C2—C3—C5—C2i | −0.54 (15) |
C1—C2—C3—C5 | −175.37 (9) | C2—C3—C4—O4 | −110.32 (11) |
C3—C2—C5i—C3i | −0.54 (15) | C2—C3—C4—O3 | 72.98 (13) |
C1—C2—C5i—C3i | 175.52 (9) | N1—C7—C8—N2 | −50.66 (12) |
C5i—C2—C3—C4 | 179.67 (9) | C6—C7—C8—N2 | −173.04 (10) |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x−1/2, −y+3/2, z+1/2; (iv) x+1/2, −y+3/2, z−1/2; (v) x+1, y, z; (vi) x, y+1, z; (vii) x−1, y, z; (viii) −x+1/2, y−1/2, −z+3/2; (ix) −x+1/2, y+1/2, −z+3/2; (x) x+1/2, −y+1/2, z−1/2; (xi) x−1/2, −y+3/2, z−1/2; (xii) x, y−1, z; (xiii) x−1/2, −y+1/2, z+1/2; (xiv) x+1/2, −y+3/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—H1W···O1ii | 0.85 (2) | 1.91 (2) | 2.7596 (17) | 172 (2) |
N1—H1A···O2xii | 0.89 | 1.98 | 2.8289 (15) | 159 |
N1—H1B···O2ii | 0.89 | 1.91 | 2.7910 (13) | 168 |
N1—H1C···O3viii | 0.89 | 1.94 | 2.8130 (14) | 168 |
OW1—H2W···O1iv | 0.81 (2) | 2.20 (2) | 2.9845 (19) | 167 (2) |
N2—H2A···O4viii | 0.89 | 1.95 | 2.8146 (14) | 165 |
N2—H2B···OW1vii | 0.89 | 1.87 | 2.7574 (17) | 172 |
N2—H2C···O4xii | 0.89 | 1.91 | 2.7918 (14) | 171 |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iv) x+1/2, −y+3/2, z−1/2; (vii) x−1, y, z; (viii) −x+1/2, y−1/2, −z+3/2; (xii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | 2C3H12N22+·C10H2O84−·2H2O |
Mr | 438.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 10.427 (2), 7.6955 (15), 12.854 (3) |
β (°) | 101.61 (3) |
V (Å3) | 1010.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.49 × 0.40 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1998) |
Tmin, Tmax | 0.940, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8157, 3038, 2727 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.713 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.112, 1.07 |
No. of reflections | 3038 |
No. of parameters | 146 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.19 |
Computer programs: SMART (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
OW1—H1W···O1i | 0.85 (2) | 1.91 (2) | 2.7596 (17) | 172 (2) |
N1—H1A···O2ii | 0.8900 | 1.9800 | 2.8289 (15) | 159.00 |
N1—H1B···O2i | 0.8900 | 1.9100 | 2.7910 (13) | 168.00 |
N1—H1C···O3iii | 0.8900 | 1.9400 | 2.8130 (14) | 168.00 |
OW1—H2W···O1iv | 0.81 (2) | 2.20 (2) | 2.9845 (19) | 167 (2) |
N2—H2A···O4iii | 0.8900 | 1.9500 | 2.8146 (14) | 165.00 |
N2—H2B···OW1v | 0.8900 | 1.8700 | 2.7574 (17) | 172.00 |
N2—H2C···O4ii | 0.8900 | 1.9100 | 2.7918 (14) | 171.00 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y−1, z; (iii) −x+1/2, y−1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) x−1, y, z. |
Acknowledgements
The authors are grateful to Islamic Azad University, North Tehran Branch for financial support.
References
Aghabozorg, H., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008). Acta Cryst. E64, o1045–o1046. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arora, K. K. & Pedireddi, V. R. (2003). J. Org. Chem. 68, 9177–9185. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Ma, L., Zhao, B. & Wang, L. (2005). Anal. Sci. 21, x85–x86. CSD CrossRef Google Scholar
Mrvos-Sermek, D., Popovic, Z. & Matkovic-Calogovic, D. (1996). Acta Cryst. C52, 2538–2541. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Rafizadeh, M., Aghayan, H. & Amani, V. (2006). Acta Cryst. E62, o5034–o5035. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C., Yin, M., Li, M., Ma, X. & Sun, J. (2005). J. Wuhan Univ. Technol. 20, 38–42. Google Scholar
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.
Several proton transfer systems using benzene- 1,2,4,5-tetracarboxylic acid (H4BTC), with nitrogen donor molecules, such as 1,10-phenanthroline, 1,7-phenanthroline, phenazine, 4-(N,N-dimethylamino)pyridine, 1,2-bis(4-pyridyl) ethene and 1,2-bis(4-pyridyl)ethane, have been synthesized and characterized by X-ray diffraction methods (Aghabozorg et al. 2008, Arora & Pedireddi, 2003). R%elated crystal structures of (H2BTC)(Hphen)2- (H4BTC) (where phen is 1,10-phenanthroline; Wang et al., 2005), (H3BTC)(Hbipy).3H2O (where bipy is 2,20-bipyridine; Ma et al., 2005), (H2BTC)(Hbipy)2(H4BTC) (Mrvos-Sermek et al., 1996) and (BTC)(H2en)2.2H2O (Rafizadeh et al. 2006) have been reported previously.
In the title compound, (C3H12N2)22+ (C10H2O8)4-. 2H2O, the asymmetric unit contains two diprotonated propane-1,2-diamine cations, one tetraanionic deprotonated anion form of benzene-1,2,4,5-tetracarboxylic acid and two water molecules (Fig. 1). The dication forms from the transfer of a single proton from each of the carboxyl groups to a propane-1,2-diamine molecule. The negative charges of one of the tetraanionic 1,2,4,5-benzenetetracarboxylate groups, is thereby neutralized by a doubly protonated propane-1,2-diammonium fragment. Crystal packing is stabilized by extensive N—H···O and O—H···O hydrogen bonding interactions involving all three species forming a supramolecular 3-D structure (Fig. 2).