Literature DB >> 21589356

Bis(propane-1,2-diammonium) benzene-1,2,4,5-tetra-carboxyl-ate dihydrate.

Hoda Pasdar, Maryam Majdolashrafi, Hossein Aghabozorg, Hamid Reza Khavasi.   

Abstract

In the crystal of the title hydrated molecular salt, 2C(3)H(12)N(2) (2+)·C(10)H(2)O(8) (4-)·2H(2)O, the packing is stabilized by extensive N-H⋯O and O-H⋯O hydrogen-bonding inter-actions involving all three species, forming a supra-molecular three-dimensional structure. The tetraanion is generated by inversion.

Entities:  

Year:  2010        PMID： 21589356      PMCID： PMC3011682          DOI： 10.1107/S1600536810044065

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

2C3H12N2 2+·C10H2O8 4−·2H2O M = 438.44 Monoclinic, a = 10.427 (2) Å b = 7.6955 (15) Å c = 12.854 (3) Å β = 101.61 (3)° V = 1010.3 (3) Å3 Z = 2 Mo Kα radiation μ = 0.12 mm−1 T = 298 K 0.49 × 0.40 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.940, T max = 0.990 8157 measured reflections 3038 independent reflections 2727 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.112 S = 1.07 3038 reflections 146 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.19 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044065/jj2064sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044065/jj2064Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
2C3H12N22+·C10H2O84−·2H2OF(000) = 468
Mr = 438.44Dx = 1.441 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8157 reflections
a = 10.427 (2) Åθ = 2.3–30.5°
b = 7.6955 (15) ŵ = 0.12 mm−1
c = 12.854 (3) ÅT = 298 K
β = 101.61 (3)°Plate, colorless
V = 1010.3 (3) Å30.49 × 0.40 × 0.08 mm
Z = 2
Bruker SMART CD area-detector diffractometer3038 independent reflections
Radiation source: fine-focus sealed tube2727 reflections with I > 2σ(I)
graphiteRint = 0.026
φ and ω scansθmax = 30.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)h = −14→14
Tmin = 0.940, Tmax = 0.990k = −10→10
8157 measured reflectionsl = −15→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0571P)2 + 0.3092P] where P = (Fo2 + 2Fc2)/3
3038 reflections(Δ/σ)max = 0.004
146 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
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.
xyzUiso*/Ueq
C10.25868 (9)0.83996 (13)1.05876 (8)0.01914 (19)
C20.12279 (9)0.91697 (12)1.02583 (7)0.01626 (18)
C30.06315 (9)0.94408 (12)0.91926 (7)0.01595 (17)
C40.12422 (9)0.88991 (13)0.82686 (7)0.01717 (18)
C5−0.05822 (9)1.02713 (13)0.89486 (7)0.01784 (18)
H5−0.09711.04570.82400.021*
C60.39782 (14)0.3316 (2)1.09027 (10)0.0389 (3)
H6A0.35870.23081.11500.047*
H6B0.37280.43321.12460.047*
H6C0.49140.32001.10670.047*
C70.35129 (11)0.34862 (15)0.97084 (9)0.0245 (2)
H70.38990.45410.94750.029*
C80.20338 (10)0.36693 (14)0.94363 (9)0.0241 (2)
H8A0.16450.27350.97740.029*
H8B0.17890.47580.97230.029*
N10.39794 (8)0.19628 (13)0.91649 (7)0.02395 (19)
H1A0.35940.10010.93330.036*
H1B0.48430.18610.93730.036*
H1C0.37790.21200.84650.036*
N20.14955 (9)0.36274 (12)0.82766 (7)0.02209 (18)
H2A0.19970.42680.79420.033*
H2B0.06850.40530.81470.033*
H2C0.14810.25360.80460.033*
O10.28549 (8)0.75595 (13)1.14363 (7)0.0344 (2)
O20.33872 (7)0.87232 (12)0.99958 (7)0.0302 (2)
O30.12767 (9)0.73323 (10)0.80446 (7)0.02951 (19)
O40.16276 (8)1.01227 (10)0.77470 (6)0.02490 (18)
OW10.89422 (11)0.47495 (18)0.80452 (13)0.0566 (4)
H1W0.833 (2)0.408 (3)0.8154 (16)0.052 (5)*
H2W0.869 (2)0.559 (3)0.769 (2)0.065 (7)*
U11U22U33U12U13U23
C10.0145 (4)0.0196 (4)0.0234 (4)0.0020 (3)0.0040 (3)0.0006 (3)
C20.0141 (4)0.0176 (4)0.0179 (4)0.0015 (3)0.0053 (3)0.0012 (3)
C30.0154 (4)0.0171 (4)0.0167 (4)0.0003 (3)0.0067 (3)−0.0010 (3)
C40.0160 (4)0.0199 (4)0.0167 (4)0.0015 (3)0.0059 (3)−0.0016 (3)
C50.0161 (4)0.0230 (4)0.0148 (4)0.0020 (3)0.0040 (3)0.0008 (3)
C60.0414 (7)0.0510 (8)0.0217 (5)−0.0021 (6)0.0002 (5)−0.0028 (5)
C70.0240 (5)0.0262 (5)0.0229 (5)−0.0040 (4)0.0038 (4)−0.0001 (4)
C80.0241 (5)0.0253 (5)0.0243 (5)0.0013 (4)0.0086 (4)−0.0007 (4)
N10.0187 (4)0.0302 (5)0.0234 (4)0.0020 (3)0.0052 (3)0.0036 (3)
N20.0202 (4)0.0208 (4)0.0257 (4)0.0013 (3)0.0058 (3)0.0023 (3)
O10.0243 (4)0.0431 (5)0.0355 (5)0.0087 (3)0.0055 (3)0.0183 (4)
O20.0167 (3)0.0416 (5)0.0345 (4)0.0056 (3)0.0107 (3)0.0097 (4)
O30.0440 (5)0.0192 (4)0.0302 (4)−0.0002 (3)0.0189 (3)−0.0043 (3)
O40.0322 (4)0.0211 (4)0.0262 (4)−0.0002 (3)0.0174 (3)0.0001 (3)
OW10.0266 (5)0.0496 (7)0.0948 (10)0.0052 (5)0.0151 (5)0.0303 (7)
O1—C11.2504 (14)C1—C21.5155 (14)
O2—C11.2620 (13)C2—C5i1.3978 (13)
O3—C41.2418 (13)C2—C31.4014 (13)
O4—C41.2673 (13)C3—C51.3959 (14)
OW1—H1W0.85 (2)C3—C41.5147 (13)
OW1—H2W0.81 (2)C5—H50.9300
N1—C71.4953 (15)C6—C71.5197 (17)
N2—C81.4837 (15)C7—C81.5178 (16)
N1—H1B0.8900C6—H6B0.9600
N1—H1C0.8900C6—H6C0.9600
N1—H1A0.8900C6—H6A0.9600
N2—H2C0.8900C7—H70.9800
N2—H2B0.8900C8—H8B0.9700
N2—H2A0.8900C8—H8A0.9700
O1···OW1ii2.7596 (17)C3···H8Avi2.7900
O1···OW1iii2.9845 (19)C4···H2Cvi2.8300
OW1···O1iv2.9845 (19)C4···H1Avi3.0300
OW1···O3v3.1427 (17)C4···H2Aix2.6500
OW1···N2v2.7574 (17)C4···H1Cix2.6100
OW1···O1ii2.7596 (17)C5···H8Avi3.0200
O2···C42.8198 (14)C6···H7ii2.8800
O2···O33.1713 (14)C7···H7ii3.0900
O2···N1vi2.8289 (15)H1W···H2Bv2.4600
O2···N1ii2.7910 (13)H1W···O1ii1.91 (2)
O3···C83.3468 (16)H1W···C1ii2.79 (2)
O3···O23.1713 (14)H1A···C4xii3.0300
O3···C13.3806 (16)H1A···O2xii1.9800
O3···N22.8710 (14)H1A···H6A2.5400
O3···OW1vii3.1427 (17)H1A···H8A2.5900
O3···O4viii3.0979 (14)H1A···C1xii2.9000
O3···N1ix2.8130 (14)H1A···O4xii2.6700
O4···N2vi2.7918 (14)H1B···O1ii2.8400
O4···N2ix2.8146 (14)H1B···C1ii2.6800
O4···N1vi3.0889 (14)H1B···O2ii1.9100
O4···C7ix3.3738 (16)H1B···H6C2.4000
O4···O3ix3.0979 (14)H1C···O4xii2.7200
O1···H1Bii2.8400H1C···C4viii2.6100
O1···H6B2.6700H1C···O3viii1.9400
O1···H5i2.5900H1C···O4viii2.7700
O1···H2Wiii2.20 (2)H1C···H2A2.4800
O1···H1Wii1.91 (2)H1C···H2C2.3700
OW1···H6Ax2.8700H1C···N22.6200
OW1···H2Bv1.8700H2W···C1iv2.83 (2)
O2···H1Avi1.9800H2W···H2Bv2.3600
O2···H6Cii2.8600H2W···O1iv2.20 (2)
O2···H1Bii1.9100H2A···O4viii1.9500
O3···H8B2.9000H2A···N12.9300
O3···H2Aix2.8300H2A···O32.4900
O3···H1Cix1.9400H2A···C4viii2.6500
O3···H2A2.4900H2A···O3viii2.8300
O3···H2B2.6100H2A···H1C2.4800
O4···H2Aix1.9500H2A···H72.5100
O4···H1Cix2.7700H2B···O32.6100
O4···H52.9200H2B···H2Wvii2.3600
O4···H7ix2.8300H2B···OW1vii1.8700
O4···H6Cxi2.8200H2B···H1Wvii2.4600
O4···H2Cvi1.9100H2C···C3xii3.0300
O4···H1Avi2.6700H2C···N12.7500
O4···H1Cvi2.7200H2C···H1C2.3700
N1···N22.9090 (15)H2C···O4xii1.9100
N1···O2xii2.8289 (15)H2C···C4xii2.8300
N1···O4xii3.0889 (14)H5···O1i2.5900
N1···C4viii3.4304 (15)H5···H6Bxi2.5200
N1···O2ii2.7910 (13)H5···O42.9200
N1···O3viii2.8130 (14)H6A···OW1xiii2.8700
N2···O4viii2.8146 (14)H6A···H1A2.5400
N2···O32.8710 (14)H6A···H8A2.4300
N2···O4xii2.7918 (14)H6B···H5xiv2.5200
N2···N12.9090 (15)H6B···H8B2.5400
N2···C4viii3.3822 (15)H6B···O12.6700
N2···OW1vii2.7574 (17)H6C···O2ii2.8600
N1···H2C2.7500H6C···H7ii2.3200
N1···H2A2.9300H6C···H1B2.4000
N2···H1C2.6200H6C···O4xiv2.8200
C1···O33.3806 (16)H7···H6Cii2.3200
C3···C8vi3.5554 (16)H7···H7ii2.5200
C4···N1ix3.4304 (15)H7···C7ii3.0900
C4···O22.8198 (14)H7···H2A2.5100
C4···N2ix3.3822 (15)H7···O4viii2.8300
C7···O4viii3.3738 (16)H7···C6ii2.8800
C8···O33.3468 (16)H8A···H6A2.4300
C8···C3xii3.5554 (16)H8A···C3xii2.7900
C1···H1Bii2.6800H8A···C5xii3.0200
C1···H2Wiii2.83 (2)H8A···C2xii2.8700
C1···H1Avi2.9000H8A···H1A2.5900
C1···H8B3.0700H8B···C13.0700
C1···H1Wii2.79 (2)H8B···H6B2.5400
C2···H8Avi2.8700H8B···O32.9000
C3···H2Cvi3.0300
H1W—OW1—H2W114 (2)O3—C4—O4124.87 (10)
H1A—N1—H1C109.00O4—C4—C3116.01 (9)
H1B—N1—H1C109.00C2i—C5—C3121.67 (9)
C7—N1—H1C109.00C3—C5—H5119.00
C7—N1—H1A109.00C2i—C5—H5119.00
C7—N1—H1B109.00C6—C7—C8110.11 (10)
H1A—N1—H1B109.00N1—C7—C6109.67 (10)
C8—N2—H2A109.00N1—C7—C8112.09 (9)
H2A—N2—H2C110.00N2—C8—C7113.01 (9)
C8—N2—H2C109.00C7—C6—H6B109.00
H2A—N2—H2B109.00C7—C6—H6C110.00
C8—N2—H2B109.00H6A—C6—H6B109.00
H2B—N2—H2C109.00H6A—C6—H6C109.00
O2—C1—C2116.68 (9)H6B—C6—H6C109.00
O1—C1—O2124.68 (10)C7—C6—H6A109.00
O1—C1—C2118.57 (9)N1—C7—H7108.00
C1—C2—C3122.50 (9)C8—C7—H7108.00
C3—C2—C5i118.88 (9)C6—C7—H7108.00
C1—C2—C5i118.50 (9)N2—C8—H8A109.00
C2—C3—C4123.48 (9)N2—C8—H8B109.00
C2—C3—C5119.45 (9)C7—C8—H8B109.00
C4—C3—C5117.07 (8)H8A—C8—H8B108.00
O3—C4—C3119.04 (9)C7—C8—H8A109.00
O1—C1—C2—C5i32.71 (14)C5i—C2—C3—C50.53 (14)
O2—C1—C2—C331.49 (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—O468.84 (12)
C1—C2—C3—C43.77 (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—O372.98 (13)
C1—C2—C5i—C3i175.52 (9)N1—C7—C8—N2−50.66 (12)
C5i—C2—C3—C4179.67 (9)C6—C7—C8—N2−173.04 (10)
D—H···AD—HH···AD···AD—H···A
OW1—H1W···O1ii0.85 (2)1.91 (2)2.7596 (17)172 (2)
N1—H1A···O2xii0.891.982.8289 (15)159
N1—H1B···O2ii0.891.912.7910 (13)168
N1—H1C···O3viii0.891.942.8130 (14)168
OW1—H2W···O1iv0.81 (2)2.20 (2)2.9845 (19)167 (2)
N2—H2A···O4viii0.891.952.8146 (14)165
N2—H2B···OW1vii0.891.872.7574 (17)172
N2—H2C···O4xii0.891.912.7918 (14)171
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
OW1—H1W⋯O1i0.85 (2)1.91 (2)2.7596 (17)172 (2)
OW1—H2W⋯O1iv0.81 (2)2.20 (2)2.9845 (19)167 (2)
N1—H1A⋯O2ii0.891.982.8289 (15)159
N1—H1B⋯O2i0.891.912.7910 (13)168
N1—H1C⋯O3iii0.891.942.8130 (14)168
N2—H2A⋯O4iii0.891.952.8146 (14)165
N2—H2B⋯OW1v0.891.872.7574 (17)172
N2—H2C⋯O4ii0.891.912.7918 (14)171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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