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In the crystal structure of the title compound, C8H26N44+·2C4O42-, the bis­(3-ammonio­prop­yl)ethyl­enediaminium (PAED) cation lies on an inversion centre and the squarate anion (Sq2-) is in a general position. Salt formation occurs by donation of four H atoms from two squaric acid molecules to the bis­(3-amino­prop­yl)ethyl­enediamine base. In the crystal structure, the strongest inter­actions are between H atoms of NH2+ groups and squarate O atoms. All the H atoms of NH3+ groups of the PAED cation also participate in hydrogen bonding with the O atoms of the Sq2- anion, contributing to the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006295/ci2006sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006295/ci2006Isup2.hkl
Contains datablock I

CCDC reference: 601140

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(3-ammoniopropyl)ethylenediaminium bis(squarate) top
Crystal data top
C8H26N44+·2C4O42F(000) = 428
Mr = 402.41Dx = 1.433 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4300 reflections
a = 10.0027 (10) Åθ = 2.2–28.0°
b = 8.3325 (12) ŵ = 0.12 mm1
c = 12.0951 (12) ÅT = 296 K
β = 112.340 (7)°Block, colourless
V = 932.43 (19) Å30.44 × 0.42 × 0.27 mm
Z = 2
Data collection top
Stoe IPDS-II
diffractometer
2185 independent reflections
Radiation source: fine-focus sealed tube1749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 6.67 pixels mm-1θmax = 27.9°, θmin = 2.3°
ω scansh = 1313
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 109
Tmin = 0.946, Tmax = 0.975l = 1515
6003 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0405P)2 + 0.1497P]
where P = (Fo2 + 2Fc2)/3
2184 reflections(Δ/σ)max = 0.001
147 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

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
C10.38764 (13)0.46779 (15)0.16508 (11)0.0327 (3)
C20.53894 (13)0.45742 (15)0.18173 (11)0.0331 (3)
C30.50811 (13)0.31904 (15)0.10144 (11)0.0327 (3)
C40.35404 (13)0.33359 (15)0.08141 (11)0.0320 (3)
C50.02485 (14)0.41702 (16)0.29534 (13)0.0396 (3)
H5A0.09620.33200.31280.048*
H5B0.07150.51000.34260.048*
C60.02572 (15)0.45913 (17)0.16527 (13)0.0431 (3)
H6A0.05620.50000.14960.052*
H6B0.09570.54540.14910.052*
C70.09357 (13)0.32320 (18)0.07832 (12)0.0398 (3)
H7A0.16960.27430.09820.048*
H7B0.13730.36660.00190.048*
C80.05583 (14)0.06240 (18)0.00135 (13)0.0422 (3)
H8A0.10340.10290.08210.051*
H8B0.12860.01340.02260.051*
N10.09436 (14)0.36405 (16)0.33107 (12)0.0394 (3)
N20.01414 (11)0.19726 (14)0.08063 (10)0.0336 (2)
O10.31757 (10)0.55660 (12)0.20775 (9)0.0425 (2)
O20.64833 (9)0.53844 (12)0.24132 (10)0.0453 (3)
O30.57827 (10)0.22500 (12)0.06430 (10)0.0454 (3)
O40.24332 (9)0.25863 (12)0.01838 (9)0.0417 (2)
H1A0.1216 (18)0.262 (2)0.3044 (16)0.053 (5)*
H1B0.065 (2)0.348 (2)0.4087 (18)0.060 (5)*
H1C0.1629 (19)0.435 (2)0.3144 (15)0.051 (5)*
H2A0.0636 (17)0.154 (2)0.1612 (15)0.047 (4)*
H2B0.0940 (19)0.242 (2)0.0639 (15)0.054 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0290 (6)0.0340 (6)0.0325 (6)0.0008 (5)0.0088 (5)0.0006 (5)
C20.0266 (5)0.0309 (6)0.0372 (6)0.0005 (5)0.0068 (5)0.0010 (5)
C30.0292 (6)0.0317 (6)0.0359 (6)0.0014 (5)0.0111 (5)0.0007 (5)
C40.0291 (6)0.0319 (6)0.0345 (6)0.0040 (5)0.0118 (5)0.0009 (5)
C50.0313 (6)0.0364 (7)0.0493 (8)0.0012 (5)0.0133 (5)0.0066 (6)
C60.0392 (7)0.0382 (7)0.0571 (9)0.0027 (6)0.0240 (6)0.0077 (6)
C70.0312 (6)0.0503 (8)0.0378 (7)0.0052 (6)0.0131 (5)0.0101 (6)
C80.0323 (6)0.0501 (8)0.0405 (7)0.0085 (6)0.0098 (5)0.0063 (6)
N10.0422 (6)0.0357 (6)0.0419 (7)0.0057 (5)0.0179 (5)0.0033 (5)
N20.0273 (5)0.0405 (6)0.0315 (5)0.0043 (4)0.0095 (4)0.0012 (5)
O10.0328 (4)0.0491 (6)0.0440 (5)0.0021 (4)0.0127 (4)0.0104 (4)
O20.0277 (4)0.0380 (5)0.0586 (6)0.0032 (4)0.0034 (4)0.0094 (5)
O30.0354 (5)0.0470 (6)0.0551 (6)0.0015 (4)0.0186 (4)0.0106 (5)
O40.0307 (4)0.0461 (5)0.0461 (5)0.0120 (4)0.0120 (4)0.0092 (4)
Geometric parameters (Å, º) top
C1—O11.2570 (15)C6—H6B0.97
C1—C21.4514 (17)C7—N21.4966 (17)
C1—C41.4591 (18)C7—H7A0.97
C2—O21.2541 (15)C7—H7B0.97
C2—C31.4629 (17)C8—N21.4860 (17)
C3—O31.2441 (15)C8—C8i1.517 (3)
C3—C41.4712 (16)C8—H8A0.97
C4—O41.2475 (15)C8—H8B0.97
C5—N11.4816 (17)N1—H1A0.910 (19)
C5—C61.500 (2)N1—H1B0.88 (2)
C5—H5A0.97N1—H1C0.868 (19)
C5—H5B0.97N2—H2A0.977 (17)
C6—C71.519 (2)N2—H2B0.969 (18)
C6—H6A0.97
O1—C1—C2133.85 (12)N2—C7—C6112.39 (11)
O1—C1—C4135.93 (11)N2—C7—H7A109.1
C2—C1—C490.21 (10)C6—C7—H7A109.1
O2—C2—C1133.12 (12)N2—C7—H7B109.1
O2—C2—C3136.34 (11)C6—C7—H7B109.1
C1—C2—C390.53 (10)H7A—C7—H7B107.9
O3—C3—C2136.94 (11)N2—C8—C8i110.35 (13)
O3—C3—C4133.77 (12)N2—C8—H8A109.6
C2—C3—C489.29 (9)C8i—C8—H8A109.6
O4—C4—C1136.43 (11)N2—C8—H8B109.6
O4—C4—C3133.67 (12)C8i—C8—H8B109.6
C1—C4—C389.90 (9)H8A—C8—H8B108.1
N1—C5—C6112.82 (11)C5—N1—H1A109.8 (10)
N1—C5—H5A109.0C5—N1—H1B112.4 (12)
C6—C5—H5A109.0H1A—N1—H1B99.6 (16)
N1—C5—H5B109.0C5—N1—H1C112.5 (11)
C6—C5—H5B109.0H1A—N1—H1C116.5 (16)
H5A—C5—H5B107.8H1B—N1—H1C105.3 (16)
C5—C6—C7115.83 (12)C8—N2—C7111.39 (10)
C5—C6—H6A108.3C8—N2—H2A108.7 (10)
C7—C6—H6A108.3C7—N2—H2A111.3 (9)
C5—C6—H6B108.3C8—N2—H2B111.6 (10)
C7—C6—H6B108.3C7—N2—H2B111.8 (10)
H6A—C6—H6B107.4H2A—N2—H2B101.7 (13)
O1—C1—C2—O23.1 (3)O1—C1—C4—C3177.40 (16)
C4—C1—C2—O2177.54 (15)C2—C1—C4—C31.92 (10)
O1—C1—C2—C3177.41 (15)O3—C3—C4—O42.1 (3)
C4—C1—C2—C31.93 (10)C2—C3—C4—O4178.50 (15)
O2—C2—C3—O33.1 (3)O3—C3—C4—C1177.53 (15)
C1—C2—C3—O3177.49 (16)C2—C3—C4—C11.90 (10)
O2—C2—C3—C4177.52 (16)N1—C5—C6—C762.24 (15)
C1—C2—C3—C41.91 (10)C5—C6—C7—N268.65 (14)
O1—C1—C4—O42.2 (3)C8i—C8—N2—C7179.22 (14)
C2—C1—C4—O4178.51 (15)C6—C7—N2—C8177.63 (11)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2ii0.910 (19)1.94 (2)2.8390 (17)171.2 (16)
N1—H1B···O3iii0.88 (2)1.98 (2)2.7905 (17)152.4 (16)
N1—H1C···O2iv0.868 (19)1.956 (19)2.7912 (16)161.2 (16)
N2—H2A···O1ii0.977 (17)1.777 (17)2.7355 (15)166.0 (13)
N2—H2B···O40.969 (18)1.783 (18)2.7195 (14)161.4 (15)
Symmetry codes: (ii) x+1/2, y1/2, z+1/2; (iii) x1/2, y+1/2, z+1/2; (iv) x1, y, z.
 

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