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In the title compound, C10H12N42+·2C10H11N4+·4C20H12O4P·6H2O, the 1,1′-binaphthalene-2,2′-diyl phosphate anion and 5,5′-diamino-2,2′-bipyridine as hydrogen-acceptor and -donor building blocks, respectively, are combined in a supra­molecular two-dimensional hydrogen-bonding network of one centrosymmetric diprotonated diamino­bipyridin-1,1′-ium dication, two monoprotonated diamino­bipyridinium cations, four phosphate counter-anions and six water mol­ecules of crystallization. Protonation of diamino­bipyridine to the bipyridinium mono- or dication enhances the hydrogen bonding due to the primary electrostatic attraction with the anion. The packing can be rationalized by a separation of the hydro­phobic binaphthyl backbone from the hydro­philic (RO)2PO2 phosphate groups, bipyridinium cation and water components. The binaphthyl tail-to-tail packing in the hydro­phobic lamellae as well as the diamino­bipyridinium packing is governed by π–π and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021794/hg2222sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021794/hg2222Isup2.hkl
Contains datablock I

CCDC reference: 651415

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.138
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

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Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4B ... ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The reaction and crystallization conditions combine one diprotonated diaminobipyridin-1,1'-ium dication with two monoprotonated diaminobipyridinium cations in a network with four phosphate counteranions and six water molecules of crystallization (Dorn et al., 2005; Dorn et al., 2006; Janiak, Deblon & Wu, 1999; Yang et al., 2003; Yang et al., 2004). The dication sits on an inversion center which bisects the central C–C-bond and relates the two pyridinium halves of the molecule. The packing in 1 can be rationalized by a separation of the hydrophobic binaphthyl backbone from the hydrophilic (RO)2PO2- phosphate groups, bipyridinium cation and hydrate components, as seen before (Dorn et al., 2006). Fig. 1 shows a projection of the unit cell crystal packing to illustrate the lamellar or layer-like arrangement of the hydrophobic and hydrophilic regions. The latter are also highlighted by the hydrogen-bonding network as red dashes. Details of part of the hydrogen-bonding network between diaminobipyrdinium, phosphate and crystal water are visualized in Fig. 2 (see Table for bond distances and angles). The binaphthyl tail-to-tail packing in the hydrophobic lamellar as well as the diaminobipyridinium packing is governed by π-π and C–H···π interactions (Dorn et al., 2006; Janiak, 2000; Nishio, 2004).

Related literature top

For related literature, see: Dorn et al. (2005); Dorn et al. (2006); Janiak, Deblon, Wu et al. (1999); Janiak, Deblon & Wu (1999); Janiak (2000); Nishio (2004); Yang et al. (2003); Yang et al. (2004).

Experimental top

5,5'-Diamino-2,2'-bipyridine (186 mg, 0.10 mmol) (Janiak, Deblon, Wu et al., 1999) was dissolved in 50 ml of hot H2O. This solution was added to a solution of racemic 1,1'-binaphthalene-2,2'-diyl phosphoric acid (348 mg, 0.10 mmol) (Dorn et al., 2006) in 20 ml of methanol. The solvent was slowly allowed to evaporate. After two weeks yellow needles of 1 were formed and separated by filtration. Crystal yield 334 mg, 65%. Analysis calculated for C110H94N12O22P4 (2058.84): C 64.14, H 4.55, N 8.16%; found: C 63.60, H 4.77, N 8.99%. IR (KBr, ν cm-1): 3345, 1636, 1587, 1550, 1507, 1486, 1464, 1328, 1241, 1218, 1156, 1095, 1069, 992, 961, 836, 750, 717, 656, 568, 535; 1H-NMR (DMSO-d6): δ 8.03 (d, H5phosphate, 3J5,6 = 9.0 Hz), 8.02–7.99 (m, H4phosphate/H6bipyridine), 7.97 (d, H3bipyridine, 3J3,4 = 8.9 Hz), 7.46–7.40 (m, H6phosphate/H7phosphate), 7.35–7.27 (m, H8phosphate/H4bipyridine), 7.23 (d, H3phosphate, 3J3,4 = 8.1 Hz).

Refinement top

The needle morphology of the crystal gave rise to a somewhat high Rint and other R values. Yet, structure solution and refinement proceeded without problems. The quality of the data set enabled the localization and refinement of the protic hydrogen atoms.

Hydrogen atoms on carbon were calculated with appropriate riding models (AFIX 43 for aromatic CH, AFIX 13 for CH, AFIX 23 for CH2, AFIX 33 for CH3) and Ueq(H) = 1.2 Ueq(CH) or 1.5 Ueq(CH3), respectively.

Hydrogen atoms on N (NH2 and NH) and O (H2O) were found from difference Fourier maps and refined with Ueq(H) = 1.5 Ueq(N/O)

Structure description top

The reaction and crystallization conditions combine one diprotonated diaminobipyridin-1,1'-ium dication with two monoprotonated diaminobipyridinium cations in a network with four phosphate counteranions and six water molecules of crystallization (Dorn et al., 2005; Dorn et al., 2006; Janiak, Deblon & Wu, 1999; Yang et al., 2003; Yang et al., 2004). The dication sits on an inversion center which bisects the central C–C-bond and relates the two pyridinium halves of the molecule. The packing in 1 can be rationalized by a separation of the hydrophobic binaphthyl backbone from the hydrophilic (RO)2PO2- phosphate groups, bipyridinium cation and hydrate components, as seen before (Dorn et al., 2006). Fig. 1 shows a projection of the unit cell crystal packing to illustrate the lamellar or layer-like arrangement of the hydrophobic and hydrophilic regions. The latter are also highlighted by the hydrogen-bonding network as red dashes. Details of part of the hydrogen-bonding network between diaminobipyrdinium, phosphate and crystal water are visualized in Fig. 2 (see Table for bond distances and angles). The binaphthyl tail-to-tail packing in the hydrophobic lamellar as well as the diaminobipyridinium packing is governed by π-π and C–H···π interactions (Dorn et al., 2006; Janiak, 2000; Nishio, 2004).

For related literature, see: Dorn et al. (2005); Dorn et al. (2006); Janiak, Deblon, Wu et al. (1999); Janiak, Deblon & Wu (1999); Janiak (2000); Nishio (2004); Yang et al. (2003); Yang et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Crystal Impact, 2006); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Projection of the crystal packing in 1 onto the (0 1 0) plane. Hydrogen bonds are indicated as red dashes.
[Figure 2] Fig. 2. Part of the hydrogen-bonding network between diaminobipyrdinium, phosphate and crystal water in 1. Hydrogen bonds are indicated with red dashes (see Table for bond distances and angles). Symmetry code: i = – x, 1 – y, – z; ii = – 1 + x, y, z; iii = – x, 2 – y, – z; iv = x, y – 1, z; v = 1 – x, 1 – y, – z;. The naphthyl groups are depicted transparent for clarity. Displacement ellipsoids are drawn at the 50% probability level, hydrogen atoms with a standard radius of 0.135 Å.
5,5'-Diamino-2,2'-bipyridin-1,1'-dium bis(5,5'-diamino-2,2'-bipyridin-1-ium) tetrakis(rac-1,1'-binaphthalene-2,2'-diyl phosphate) hexahydrate top
Crystal data top
C10H12N42+·2C10H11N4+·4C20H12O4P·6H2OV = 2402.5 (7) Å3
Mr = 2059.86Z = 1
Triclinic, P1F(000) = 1074
Hall symbol: -P 1Dx = 1.424 Mg m3
a = 9.7001 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.102 (2) ŵ = 0.16 mm1
c = 18.244 (3) ÅT = 203 K
α = 82.940 (11)°Needle, yellow
β = 76.232 (11)°0.56 × 0.04 × 0.03 mm
γ = 85.571 (10)°
Data collection top
Bruker APEXII CCD
diffractometer
8570 independent reflections
Radiation source: fine-focus sealed tube4686 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
ω scansθmax = 25.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.914, Tmax = 0.996k = 1616
24014 measured reflectionsl = 2121
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0435P)2]
where P = (Fo2 + 2Fc2)/3
8570 reflections(Δ/σ)max < 0.001
709 parametersΔρmax = 0.31 e Å3
2 restraintsΔρmin = 0.37 e Å3
Crystal data top
C10H12N42+·2C10H11N4+·4C20H12O4P·6H2Oγ = 85.571 (10)°
Mr = 2059.86V = 2402.5 (7) Å3
Triclinic, P1Z = 1
a = 9.7001 (16) ÅMo Kα radiation
b = 14.102 (2) ŵ = 0.16 mm1
c = 18.244 (3) ÅT = 203 K
α = 82.940 (11)°0.56 × 0.04 × 0.03 mm
β = 76.232 (11)°
Data collection top
Bruker APEXII CCD
diffractometer
8570 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4686 reflections with I > 2σ(I)
Tmin = 0.914, Tmax = 0.996Rint = 0.098
24014 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0562 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.31 e Å3
8570 reflectionsΔρmin = 0.37 e Å3
709 parameters
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
P10.43917 (11)0.31213 (7)0.04758 (5)0.0382 (3)
O10.3322 (2)0.25002 (15)0.11340 (11)0.0332 (6)
O20.5291 (2)0.36183 (14)0.09484 (12)0.0328 (5)
O30.5400 (3)0.25075 (18)0.00114 (13)0.0533 (7)
O40.3487 (3)0.38558 (18)0.01291 (14)0.0542 (7)
C10.4313 (4)0.2395 (2)0.22255 (17)0.0287 (8)
C20.3948 (4)0.1947 (2)0.16755 (17)0.0296 (8)
C30.4198 (4)0.0964 (2)0.16155 (18)0.0361 (9)
H3A0.39090.06830.12390.043*
C40.4864 (4)0.0423 (2)0.21105 (18)0.0361 (9)
H4A0.50110.02390.20810.043*
C50.5339 (4)0.0834 (2)0.26684 (17)0.0313 (8)
C60.6104 (4)0.0294 (2)0.3161 (2)0.0400 (9)
H6A0.62610.03690.31380.048*
C70.6615 (4)0.0710 (2)0.3665 (2)0.0438 (10)
H70.71090.03350.39910.053*
C80.6410 (4)0.1706 (2)0.3701 (2)0.0417 (10)
H80.67940.19980.40390.050*
C90.5654 (4)0.2245 (2)0.32452 (18)0.0348 (9)
H9A0.55180.29070.32770.042*
C100.5068 (4)0.1834 (2)0.27248 (17)0.0281 (8)
C110.4023 (4)0.3453 (2)0.22337 (18)0.0299 (8)
C120.4491 (4)0.4038 (2)0.15860 (18)0.0306 (8)
C130.4266 (4)0.5036 (2)0.1525 (2)0.0359 (9)
H130.45870.54060.10590.043*
C140.3582 (4)0.5458 (2)0.2145 (2)0.0390 (9)
H140.34530.61280.21130.047*
C150.3060 (4)0.4904 (2)0.28375 (19)0.0329 (8)
C160.2358 (4)0.5335 (2)0.3490 (2)0.0409 (9)
H160.22470.60050.34630.049*
C170.1837 (4)0.4805 (2)0.4158 (2)0.0437 (10)
H170.13800.51080.45890.052*
C180.1983 (4)0.3805 (2)0.4203 (2)0.0401 (9)
H180.16200.34390.46660.048*
C190.2646 (4)0.3354 (2)0.35836 (18)0.0363 (9)
H190.27040.26820.36190.044*
C200.3246 (4)0.3891 (2)0.28876 (18)0.0311 (8)
P20.17925 (11)0.83695 (6)0.24285 (5)0.0371 (3)
O50.0731 (3)0.76467 (14)0.30098 (11)0.0341 (6)
O60.2692 (3)0.87165 (14)0.29780 (11)0.0353 (6)
O70.2716 (3)0.77708 (17)0.18815 (13)0.0511 (7)
O80.1033 (3)0.92259 (17)0.21483 (16)0.0634 (8)
C210.0630 (4)0.8089 (2)0.42500 (17)0.0284 (8)
C220.0051 (4)0.7971 (2)0.36875 (17)0.0303 (8)
C230.1514 (4)0.8136 (2)0.37639 (19)0.0348 (8)
H230.19350.80250.33700.042*
C240.2323 (4)0.8456 (2)0.44066 (19)0.0370 (9)
H240.33160.85210.44740.044*
C250.1688 (4)0.8694 (2)0.49788 (18)0.0319 (8)
C260.2476 (4)0.9113 (2)0.56202 (19)0.0382 (9)
H260.34660.92110.56870.046*
C270.1836 (4)0.9380 (2)0.6147 (2)0.0399 (9)
H270.23860.96580.65720.048*
C280.0368 (4)0.9243 (2)0.60561 (18)0.0375 (9)
H280.00690.94430.64150.045*
C290.0450 (4)0.8817 (2)0.54447 (17)0.0333 (8)
H290.14370.87240.53920.040*
C300.0190 (4)0.8520 (2)0.48986 (17)0.0280 (8)
C310.2156 (4)0.7772 (2)0.41706 (17)0.0286 (8)
C320.3135 (4)0.8064 (2)0.35202 (18)0.0311 (8)
C330.4568 (4)0.7743 (2)0.3383 (2)0.0382 (9)
H330.51980.79520.29240.046*
C340.5044 (4)0.7130 (2)0.3912 (2)0.0417 (9)
H340.60080.69240.38210.050*
C350.4116 (4)0.6802 (2)0.4595 (2)0.0365 (9)
C360.4612 (5)0.6162 (3)0.5155 (2)0.0511 (11)
H360.55880.59910.50820.061*
C370.3703 (6)0.5799 (3)0.5788 (2)0.0527 (12)
H370.40400.53780.61540.063*
C380.2246 (5)0.6055 (2)0.5896 (2)0.0493 (11)
H380.16090.57840.63300.059*
C390.1735 (4)0.6688 (2)0.53834 (18)0.0386 (9)
H390.07560.68510.54740.046*
C400.2647 (4)0.7099 (2)0.47244 (18)0.0314 (8)
N50.0910 (4)0.61714 (19)0.00186 (15)0.0356 (7)
H50.185 (4)0.607 (2)0.0068 (19)0.053*
N60.0366 (4)0.8309 (2)0.0474 (2)0.0598 (11)
H6B0.052 (4)0.867 (3)0.048 (3)0.090*
H6C0.107 (6)0.842 (3)0.060 (3)0.090*
C510.0114 (4)0.5485 (2)0.00753 (17)0.0323 (8)
C520.1320 (4)0.5762 (2)0.02711 (19)0.0408 (9)
H520.20710.53100.03080.049*
C530.0831 (4)0.7077 (2)0.01407 (18)0.0374 (9)
H530.15830.75200.00840.045*
C540.0332 (4)0.7378 (2)0.03484 (19)0.0417 (9)
C550.1423 (4)0.6689 (2)0.0411 (2)0.0435 (9)
H550.22370.68590.05500.052*
N10.8043 (3)0.2825 (2)0.15243 (15)0.0362 (7)
H10.738 (4)0.326 (2)0.1374 (19)0.054*
N20.7674 (3)0.46415 (19)0.17645 (15)0.0390 (7)
N30.8985 (4)0.0303 (2)0.14736 (19)0.0504 (9)
H3B0.951 (5)0.015 (3)0.169 (2)0.076*
H3C0.836 (5)0.007 (3)0.121 (2)0.076*
N40.8107 (4)0.7086 (2)0.20931 (18)0.0449 (8)
H4B0.883 (5)0.742 (3)0.210 (2)0.067*
H4C0.745 (4)0.742 (3)0.181 (2)0.067*
C410.8992 (4)0.3158 (2)0.18548 (18)0.0354 (8)
C420.9989 (4)0.2483 (2)0.20719 (19)0.0410 (9)
H421.06750.26760.23020.049*
C430.9982 (4)0.1544 (2)0.19537 (19)0.0399 (9)
H431.06590.11020.21100.048*
C440.8984 (4)0.1225 (2)0.16032 (19)0.0386 (9)
C450.7994 (4)0.1913 (2)0.13969 (19)0.0374 (9)
H450.72930.17370.11690.045*
C460.8861 (4)0.4183 (2)0.19335 (18)0.0350 (8)
C470.9849 (4)0.4665 (2)0.21622 (19)0.0431 (9)
H471.06610.43340.22790.052*
C480.9633 (4)0.5637 (3)0.22177 (19)0.0438 (9)
H481.02990.59720.23710.053*
C490.8424 (4)0.6115 (2)0.20454 (18)0.0383 (9)
C500.7481 (4)0.5573 (2)0.1819 (2)0.0422 (9)
H500.66610.58880.16980.051*
O90.5612 (3)0.7794 (2)0.13189 (16)0.0515 (8)
H9B0.547 (5)0.758 (3)0.093 (3)0.077*
H9C0.471 (5)0.787 (3)0.155 (3)0.077*
O100.7472 (3)0.9282 (2)0.05583 (17)0.0573 (8)
H10A0.718 (5)0.973 (3)0.018 (2)0.086*
H10B0.674 (5)0.891 (3)0.084 (3)0.086*
O110.3160 (4)0.9211 (2)0.04676 (17)0.0750 (10)
H11A0.298 (7)0.914 (4)0.091 (3)0.113*
H11B0.386 (6)0.880 (4)0.025 (3)0.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0350 (6)0.0509 (6)0.0303 (5)0.0097 (5)0.0106 (5)0.0004 (4)
O10.0283 (15)0.0428 (13)0.0287 (12)0.0061 (11)0.0065 (11)0.0014 (10)
O20.0252 (14)0.0410 (12)0.0327 (13)0.0064 (11)0.0069 (11)0.0031 (10)
O30.0499 (19)0.0655 (17)0.0447 (15)0.0162 (14)0.0003 (14)0.0212 (13)
O40.0422 (18)0.0667 (16)0.0574 (16)0.0151 (14)0.0280 (15)0.0194 (13)
C10.026 (2)0.0312 (17)0.0271 (17)0.0029 (15)0.0020 (16)0.0048 (14)
C20.025 (2)0.0344 (18)0.0288 (18)0.0005 (15)0.0065 (16)0.0029 (14)
C30.040 (2)0.0388 (19)0.0314 (19)0.0115 (17)0.0061 (18)0.0099 (15)
C40.042 (2)0.0248 (16)0.041 (2)0.0055 (16)0.0052 (19)0.0079 (15)
C50.031 (2)0.0301 (17)0.0308 (18)0.0018 (15)0.0034 (17)0.0024 (14)
C60.041 (2)0.0291 (17)0.049 (2)0.0017 (17)0.010 (2)0.0052 (16)
C70.041 (3)0.041 (2)0.052 (2)0.0053 (18)0.020 (2)0.0009 (17)
C80.045 (3)0.040 (2)0.048 (2)0.0001 (18)0.027 (2)0.0055 (16)
C90.038 (2)0.0320 (18)0.0362 (19)0.0016 (16)0.0127 (18)0.0063 (15)
C100.025 (2)0.0283 (16)0.0283 (18)0.0039 (14)0.0017 (16)0.0023 (13)
C110.027 (2)0.0318 (17)0.0332 (19)0.0049 (15)0.0119 (17)0.0015 (15)
C120.022 (2)0.0377 (18)0.0317 (19)0.0008 (15)0.0045 (16)0.0041 (15)
C130.035 (2)0.0331 (18)0.040 (2)0.0065 (16)0.0120 (18)0.0046 (16)
C140.041 (2)0.0267 (17)0.050 (2)0.0053 (16)0.013 (2)0.0008 (16)
C150.029 (2)0.0294 (17)0.043 (2)0.0021 (15)0.0121 (18)0.0067 (15)
C160.042 (3)0.0281 (17)0.056 (2)0.0003 (17)0.013 (2)0.0131 (17)
C170.046 (3)0.040 (2)0.045 (2)0.0021 (18)0.004 (2)0.0179 (18)
C180.038 (2)0.042 (2)0.039 (2)0.0019 (17)0.0041 (19)0.0093 (16)
C190.037 (2)0.0325 (18)0.040 (2)0.0022 (16)0.0065 (18)0.0073 (16)
C200.031 (2)0.0306 (17)0.0340 (19)0.0009 (15)0.0119 (17)0.0038 (15)
P20.0438 (7)0.0362 (5)0.0303 (5)0.0028 (4)0.0073 (5)0.0013 (4)
O50.0390 (16)0.0327 (12)0.0299 (12)0.0019 (11)0.0033 (12)0.0093 (10)
O60.0426 (16)0.0315 (12)0.0305 (12)0.0063 (11)0.0058 (12)0.0001 (10)
O70.0531 (19)0.0622 (16)0.0335 (14)0.0117 (13)0.0089 (13)0.0198 (12)
O80.073 (2)0.0460 (15)0.0757 (19)0.0024 (14)0.0383 (18)0.0118 (13)
C210.028 (2)0.0295 (16)0.0271 (18)0.0028 (15)0.0041 (16)0.0021 (14)
C220.030 (2)0.0299 (17)0.0287 (18)0.0015 (15)0.0017 (17)0.0061 (14)
C230.035 (2)0.0379 (19)0.034 (2)0.0037 (17)0.0120 (18)0.0040 (15)
C240.028 (2)0.0383 (19)0.043 (2)0.0025 (16)0.0074 (19)0.0049 (16)
C250.032 (2)0.0264 (17)0.0321 (19)0.0040 (15)0.0027 (17)0.0012 (14)
C260.036 (2)0.0311 (18)0.041 (2)0.0012 (16)0.0020 (19)0.0003 (16)
C270.041 (3)0.0359 (19)0.037 (2)0.0047 (17)0.0067 (19)0.0100 (16)
C280.049 (3)0.0351 (18)0.0276 (19)0.0079 (17)0.0031 (18)0.0085 (15)
C290.036 (2)0.0316 (17)0.0339 (19)0.0014 (16)0.0116 (18)0.0067 (14)
C300.030 (2)0.0238 (16)0.0272 (18)0.0020 (14)0.0003 (16)0.0044 (13)
C310.031 (2)0.0269 (16)0.0306 (18)0.0024 (15)0.0094 (17)0.0094 (14)
C320.033 (2)0.0304 (17)0.0310 (19)0.0046 (16)0.0080 (18)0.0061 (14)
C330.032 (2)0.0375 (19)0.045 (2)0.0062 (17)0.0016 (19)0.0120 (16)
C340.029 (2)0.044 (2)0.057 (2)0.0032 (17)0.015 (2)0.0180 (18)
C350.041 (2)0.0311 (18)0.043 (2)0.0008 (17)0.015 (2)0.0155 (16)
C360.058 (3)0.044 (2)0.062 (3)0.012 (2)0.035 (3)0.016 (2)
C370.083 (4)0.038 (2)0.046 (2)0.014 (2)0.034 (3)0.0069 (18)
C380.077 (4)0.0344 (19)0.034 (2)0.001 (2)0.010 (2)0.0041 (16)
C390.046 (3)0.0368 (19)0.034 (2)0.0005 (18)0.0095 (19)0.0091 (16)
C400.038 (2)0.0281 (17)0.0313 (19)0.0034 (16)0.0104 (18)0.0091 (14)
N50.036 (2)0.0374 (16)0.0349 (16)0.0057 (15)0.0100 (15)0.0039 (13)
N60.050 (3)0.049 (2)0.084 (3)0.0069 (18)0.013 (2)0.0250 (19)
C510.031 (2)0.0375 (18)0.0270 (18)0.0064 (16)0.0027 (16)0.0028 (14)
C520.033 (2)0.044 (2)0.047 (2)0.0038 (17)0.0092 (19)0.0076 (17)
C530.039 (2)0.038 (2)0.034 (2)0.0024 (17)0.0057 (18)0.0051 (15)
C540.040 (3)0.042 (2)0.041 (2)0.0120 (18)0.0005 (19)0.0093 (16)
C550.034 (2)0.050 (2)0.049 (2)0.0087 (19)0.007 (2)0.0136 (18)
N10.0306 (19)0.0391 (17)0.0387 (17)0.0014 (14)0.0097 (15)0.0007 (13)
N20.033 (2)0.0403 (17)0.0443 (18)0.0010 (14)0.0104 (16)0.0060 (13)
N30.051 (2)0.0400 (19)0.063 (2)0.0045 (16)0.0210 (19)0.0071 (16)
N40.041 (2)0.0436 (19)0.052 (2)0.0053 (15)0.0072 (18)0.0182 (15)
C410.032 (2)0.0420 (19)0.0311 (19)0.0027 (17)0.0072 (18)0.0008 (15)
C420.034 (2)0.050 (2)0.038 (2)0.0044 (18)0.0091 (19)0.0019 (17)
C430.036 (2)0.044 (2)0.038 (2)0.0050 (18)0.0098 (19)0.0018 (16)
C440.030 (2)0.046 (2)0.037 (2)0.0005 (18)0.0057 (18)0.0000 (16)
C450.030 (2)0.043 (2)0.039 (2)0.0024 (17)0.0080 (18)0.0022 (16)
C460.032 (2)0.044 (2)0.0286 (18)0.0074 (17)0.0049 (17)0.0015 (15)
C470.036 (2)0.050 (2)0.046 (2)0.0046 (19)0.014 (2)0.0046 (17)
C480.038 (3)0.055 (2)0.041 (2)0.0087 (19)0.0097 (19)0.0112 (17)
C490.039 (2)0.044 (2)0.0294 (19)0.0045 (18)0.0013 (18)0.0090 (15)
C500.037 (2)0.044 (2)0.048 (2)0.0004 (18)0.013 (2)0.0095 (17)
O90.0481 (19)0.0677 (18)0.0424 (17)0.0006 (16)0.0129 (15)0.0161 (13)
O100.055 (2)0.0572 (18)0.0596 (19)0.0041 (15)0.0156 (17)0.0004 (14)
O110.083 (3)0.086 (2)0.0466 (18)0.0059 (18)0.008 (2)0.0079 (17)
Geometric parameters (Å, º) top
P1—O31.463 (3)C29—H290.9400
P1—O41.485 (2)C31—C321.372 (5)
P1—O11.605 (2)C31—C401.439 (4)
P1—O21.612 (2)C32—C331.402 (5)
O1—C21.406 (3)C33—C341.356 (5)
O2—C121.405 (4)C33—H330.9400
C1—C21.375 (4)C34—C351.401 (5)
C1—C101.430 (4)C34—H340.9400
C1—C111.498 (4)C35—C361.425 (5)
C2—C31.403 (4)C35—C401.427 (5)
C3—C41.359 (4)C36—C371.346 (6)
C3—H3A0.9400C36—H360.9400
C4—C51.412 (4)C37—C381.404 (6)
C4—H4A0.9400C37—H370.9400
C5—C61.414 (4)C38—C391.366 (4)
C5—C101.426 (4)C38—H380.9400
C6—C71.352 (5)C39—C401.402 (5)
C6—H6A0.9400C39—H390.9400
C7—C81.411 (5)N5—C531.333 (4)
C7—H70.9400N5—C511.345 (4)
C8—C91.362 (4)N5—H50.98 (4)
C8—H80.9400N6—C541.364 (5)
C9—C101.415 (4)N6—H6B0.96 (4)
C9—H9A0.9400N6—H6C0.81 (5)
C11—C121.359 (4)C51—C521.397 (5)
C11—C201.433 (4)C51—C51i1.472 (6)
C12—C131.402 (4)C52—C551.377 (5)
C13—C141.349 (5)C52—H520.9400
C13—H130.9400C53—C541.384 (5)
C14—C151.406 (5)C53—H530.9400
C14—H140.9400C54—C551.397 (5)
C15—C161.407 (5)C55—H550.9400
C15—C201.420 (4)N1—C451.342 (4)
C16—C171.356 (5)N1—C411.353 (4)
C16—H160.9400N1—H10.92 (4)
C17—C181.401 (5)N2—C501.324 (4)
C17—H170.9400N2—C461.358 (4)
C18—C191.365 (5)N3—C441.350 (4)
C18—H180.9400N3—H3B0.90 (4)
C19—C201.416 (5)N3—H3C0.96 (4)
C19—H190.9400N4—C491.389 (4)
P2—O81.467 (2)N4—H4B0.87 (4)
P2—O71.475 (3)N4—H4C0.97 (3)
P2—O51.612 (2)C41—C421.395 (4)
P2—O61.615 (2)C41—C461.464 (5)
O5—C221.397 (4)C42—C431.368 (5)
O6—C321.388 (3)C42—H420.9400
C21—C221.377 (4)C43—C441.408 (5)
C21—C301.434 (4)C43—H430.9400
C21—C311.491 (5)C44—C451.394 (5)
C22—C231.397 (5)C45—H450.9400
C23—C241.354 (5)C46—C471.383 (5)
C23—H230.9400C47—C481.383 (5)
C24—C251.417 (5)C47—H470.9400
C24—H240.9400C48—C491.389 (5)
C25—C261.406 (5)C48—H480.9400
C25—C301.430 (5)C49—C501.399 (5)
C26—C271.363 (5)C50—H500.9400
C26—H260.9400O9—H9B0.85 (4)
C27—C281.395 (5)O9—H9C0.88 (5)
C27—H270.9400O10—H10A0.96 (4)
C28—C291.380 (5)O10—H10B0.93 (5)
C28—H280.9400O11—H11A0.78 (5)
C29—C301.411 (4)O11—H11B0.91 (6)
O3—P1—O4119.31 (15)C28—C29—C30120.3 (4)
O3—P1—O1111.34 (14)C28—C29—H29119.9
O4—P1—O1105.91 (15)C30—C29—H29119.9
O3—P1—O2106.68 (14)C29—C30—C25118.9 (3)
O4—P1—O2110.01 (14)C29—C30—C21121.8 (3)
O1—P1—O2102.33 (12)C25—C30—C21119.3 (3)
C2—O1—P1115.4 (2)C32—C31—C40117.4 (3)
C12—O2—P1115.8 (2)C32—C31—C21119.7 (3)
C2—C1—C10117.6 (3)C40—C31—C21122.7 (3)
C2—C1—C11119.2 (3)C31—C32—O6118.7 (3)
C10—C1—C11123.0 (3)C31—C32—C33122.9 (3)
C1—C2—C3123.3 (3)O6—C32—C33118.4 (3)
C1—C2—O1118.8 (3)C34—C33—C32119.8 (3)
C3—C2—O1117.9 (3)C34—C33—H33120.1
C4—C3—C2118.9 (3)C32—C33—H33120.1
C4—C3—H3A120.5C33—C34—C35120.8 (3)
C2—C3—H3A120.5C33—C34—H34119.6
C3—C4—C5121.5 (3)C35—C34—H34119.6
C3—C4—H4A119.2C34—C35—C36121.1 (4)
C5—C4—H4A119.2C34—C35—C40119.4 (3)
C4—C5—C6122.4 (3)C36—C35—C40119.5 (4)
C4—C5—C10118.8 (3)C37—C36—C35120.9 (4)
C6—C5—C10118.8 (3)C37—C36—H36119.6
C7—C6—C5121.5 (3)C35—C36—H36119.6
C7—C6—H6A119.2C36—C37—C38119.5 (3)
C5—C6—H6A119.2C36—C37—H37120.3
C6—C7—C8120.2 (3)C38—C37—H37120.3
C6—C7—H7119.9C39—C38—C37121.4 (4)
C8—C7—H7119.9C39—C38—H38119.3
C9—C8—C7119.8 (3)C37—C38—H38119.3
C9—C8—H8120.1C38—C39—C40121.1 (4)
C7—C8—H8120.1C38—C39—H39119.5
C8—C9—C10121.8 (3)C40—C39—H39119.5
C8—C9—H9A119.1C39—C40—C35117.5 (3)
C10—C9—H9A119.1C39—C40—C31123.0 (3)
C9—C10—C5117.8 (3)C35—C40—C31119.4 (3)
C9—C10—C1122.3 (3)C53—N5—C51123.8 (3)
C5—C10—C1119.7 (3)C53—N5—H5110 (2)
C12—C11—C20117.4 (3)C51—N5—H5126 (2)
C12—C11—C1119.0 (3)C54—N6—H6B114 (3)
C20—C11—C1123.6 (3)C54—N6—H6C113 (4)
C11—C12—C13123.9 (3)H6B—N6—H6C132 (5)
C11—C12—O2117.8 (3)N5—C51—C52116.5 (3)
C13—C12—O2118.2 (3)N5—C51—C51i118.1 (4)
C14—C13—C12119.1 (3)C52—C51—C51i125.4 (4)
C14—C13—H13120.4C55—C52—C51120.9 (3)
C12—C13—H13120.4C55—C52—H52119.5
C13—C14—C15120.6 (3)C51—C52—H52119.5
C13—C14—H14119.7N5—C53—C54121.6 (3)
C15—C14—H14119.7N5—C53—H53119.2
C14—C15—C16121.2 (3)C54—C53—H53119.2
C14—C15—C20120.0 (3)N6—C54—C53119.7 (4)
C16—C15—C20118.8 (3)N6—C54—C55123.8 (4)
C17—C16—C15121.5 (3)C53—C54—C55116.4 (3)
C17—C16—H16119.2C52—C55—C54120.7 (4)
C15—C16—H16119.2C52—C55—H55119.7
C16—C17—C18119.7 (3)C54—C55—H55119.7
C16—C17—H17120.1C45—N1—C41125.2 (3)
C18—C17—H17120.1C45—N1—H1118 (2)
C19—C18—C17120.9 (3)C41—N1—H1117 (2)
C19—C18—H18119.5C50—N2—C46118.3 (3)
C17—C18—H18119.5C44—N3—H3B120 (3)
C18—C19—C20120.4 (3)C44—N3—H3C124 (2)
C18—C19—H19119.8H3B—N3—H3C115 (4)
C20—C19—H19119.8C49—N4—H4B115 (3)
C19—C20—C15118.4 (3)C49—N4—H4C119 (2)
C19—C20—C11122.6 (3)H4B—N4—H4C114 (4)
C15—C20—C11118.9 (3)N1—C41—C42116.0 (3)
O8—P2—O7119.53 (16)N1—C41—C46116.2 (3)
O8—P2—O5112.15 (16)C42—C41—C46127.7 (3)
O7—P2—O5105.55 (14)C43—C42—C41120.9 (3)
O8—P2—O6106.54 (14)C43—C42—H42119.6
O7—P2—O6109.94 (15)C41—C42—H42119.6
O5—P2—O6101.72 (12)C42—C43—C44121.5 (3)
C22—O5—P2118.05 (19)C42—C43—H43119.2
C32—O6—P2120.11 (19)C44—C43—H43119.2
C22—C21—C30117.2 (3)N3—C44—C45121.8 (4)
C22—C21—C31120.1 (3)N3—C44—C43121.9 (3)
C30—C21—C31122.7 (3)C45—C44—C43116.4 (3)
C21—C22—C23123.2 (3)N1—C45—C44120.0 (3)
C21—C22—O5119.6 (3)N1—C45—H45120.0
C23—C22—O5117.2 (3)C44—C45—H45120.0
C24—C23—C22119.8 (3)N2—C46—C47121.5 (3)
C24—C23—H23120.1N2—C46—C41114.6 (3)
C22—C23—H23120.1C47—C46—C41123.8 (3)
C23—C24—C25120.6 (3)C48—C47—C46119.6 (3)
C23—C24—H24119.7C48—C47—H47120.2
C25—C24—H24119.7C46—C47—H47120.2
C26—C25—C24122.2 (3)C47—C48—C49119.5 (4)
C26—C25—C30118.5 (3)C47—C48—H48120.3
C24—C25—C30119.2 (3)C49—C48—H48120.3
C27—C26—C25121.5 (4)C48—C49—N4123.6 (3)
C27—C26—H26119.3C48—C49—C50117.2 (3)
C25—C26—H26119.3N4—C49—C50119.2 (3)
C26—C27—C28120.1 (3)N2—C50—C49123.9 (3)
C26—C27—H27119.9N2—C50—H50118.0
C28—C27—H27119.9C49—C50—H50118.0
C29—C28—C27120.7 (3)H9B—O9—H9C97 (4)
C29—C28—H28119.7H10A—O10—H10B112 (4)
C27—C28—H28119.7H11A—O11—H11B113 (5)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.92 (4)2.33 (4)3.172 (4)151 (3)
N3—H3B···O8ii0.90 (4)1.97 (4)2.830 (4)161 (4)
N3—H3C···O10iii0.96 (4)2.08 (5)3.016 (5)164 (4)
N4—H4C···O90.97 (3)2.18 (4)3.124 (5)163 (4)
N5—H5···O4i0.98 (4)1.61 (4)2.581 (4)167 (3)
N6—H6B···O10iv0.96 (4)2.05 (4)3.006 (5)173 (4)
N6—H6C···O110.81 (5)2.34 (5)3.078 (6)153 (5)
O9—H9B···O3v0.85 (4)2.06 (4)2.875 (4)159 (4)
O9—H9C···O70.88 (5)1.89 (5)2.753 (4)164 (4)
O10—H10A···O11vi0.96 (4)1.85 (4)2.787 (4)166 (4)
O10—H10B···O90.93 (5)1.98 (5)2.874 (4)162 (4)
O11—H11B···O3v0.91 (6)1.99 (5)2.817 (4)151 (5)
O11—H11A···O70.78 (5)2.44 (5)3.046 (4)136 (5)
O11—H11A···O80.78 (5)2.59 (6)3.264 (5)147 (6)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1, z; (iii) x, y1, z; (iv) x1, y, z; (v) x+1, y+1, z; (vi) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC10H12N42+·2C10H11N4+·4C20H12O4P·6H2O
Mr2059.86
Crystal system, space groupTriclinic, P1
Temperature (K)203
a, b, c (Å)9.7001 (16), 14.102 (2), 18.244 (3)
α, β, γ (°)82.940 (11), 76.232 (11), 85.571 (10)
V3)2402.5 (7)
Z1
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.56 × 0.04 × 0.03
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.914, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
24014, 8570, 4686
Rint0.098
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.138, 0.99
No. of reflections8570
No. of parameters709
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.37

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Crystal Impact, 2006), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.92 (4)2.33 (4)3.172 (4)151 (3)
N3—H3B···O8i0.90 (4)1.97 (4)2.830 (4)161 (4)
N3—H3C···O10ii0.96 (4)2.08 (5)3.016 (5)164 (4)
N4—H4C···O90.97 (3)2.18 (4)3.124 (5)163 (4)
N5—H5···O4iii0.98 (4)1.61 (4)2.581 (4)167 (3)
N6—H6B···O10iv0.96 (4)2.05 (4)3.006 (5)173 (4)
N6—H6C···O110.81 (5)2.34 (5)3.078 (6)153 (5)
O9—H9B···O3v0.85 (4)2.06 (4)2.875 (4)159 (4)
O9—H9C···O70.88 (5)1.89 (5)2.753 (4)164 (4)
O10—H10A···O11vi0.96 (4)1.85 (4)2.787 (4)166 (4)
O10—H10B···O90.93 (5)1.98 (5)2.874 (4)162 (4)
O11—H11B···O3v0.91 (6)1.99 (5)2.817 (4)151 (5)
O11—H11A···O70.78 (5)2.44 (5)3.046 (4)136 (5)
O11—H11A···O80.78 (5)2.59 (6)3.264 (5)147 (6)
Symmetry codes: (i) x+1, y1, z; (ii) x, y1, z; (iii) x, y+1, z; (iv) x1, y, z; (v) x+1, y+1, z; (vi) x+1, y+2, z.
 

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