Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021794/hg2222sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021794/hg2222Isup2.hkl |
CCDC reference: 651415
Key indicators
- Single-crystal X-ray study
- T = 203 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.138
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
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
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).
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).
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)
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).
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.
C10H12N42+·2C10H11N4+·4C20H12O4P−·6H2O | V = 2402.5 (7) Å3 |
Mr = 2059.86 | Z = 1 |
Triclinic, P1 | F(000) = 1074 |
Hall symbol: -P 1 | Dx = 1.424 Mg m−3 |
a = 9.7001 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.102 (2) Å | µ = 0.16 mm−1 |
c = 18.244 (3) Å | T = 203 K |
α = 82.940 (11)° | Needle, yellow |
β = 76.232 (11)° | 0.56 × 0.04 × 0.03 mm |
γ = 85.571 (10)° |
Bruker APEXII CCD diffractometer | 8570 independent reflections |
Radiation source: fine-focus sealed tube | 4686 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
ω scans | θmax = 25.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.914, Tmax = 0.996 | k = −16→16 |
24014 measured reflections | l = −21→21 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H 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 parameters | Δρmax = 0.31 e Å−3 |
2 restraints | Δρmin = −0.37 e Å−3 |
C10H12N42+·2C10H11N4+·4C20H12O4P−·6H2O | γ = 85.571 (10)° |
Mr = 2059.86 | V = 2402.5 (7) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.7001 (16) Å | Mo Kα radiation |
b = 14.102 (2) Å | µ = 0.16 mm−1 |
c = 18.244 (3) Å | T = 203 K |
α = 82.940 (11)° | 0.56 × 0.04 × 0.03 mm |
β = 76.232 (11)° |
Bruker APEXII CCD diffractometer | 8570 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4686 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.996 | Rint = 0.098 |
24014 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 2 restraints |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.31 e Å−3 |
8570 reflections | Δρmin = −0.37 e Å−3 |
709 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 | ||
P1 | 0.43917 (11) | 0.31213 (7) | 0.04758 (5) | 0.0382 (3) | |
O1 | 0.3322 (2) | 0.25002 (15) | 0.11340 (11) | 0.0332 (6) | |
O2 | 0.5291 (2) | 0.36183 (14) | 0.09484 (12) | 0.0328 (5) | |
O3 | 0.5400 (3) | 0.25075 (18) | −0.00114 (13) | 0.0533 (7) | |
O4 | 0.3487 (3) | 0.38558 (18) | 0.01291 (14) | 0.0542 (7) | |
C1 | 0.4313 (4) | 0.2395 (2) | 0.22255 (17) | 0.0287 (8) | |
C2 | 0.3948 (4) | 0.1947 (2) | 0.16755 (17) | 0.0296 (8) | |
C3 | 0.4198 (4) | 0.0964 (2) | 0.16155 (18) | 0.0361 (9) | |
H3A | 0.3909 | 0.0683 | 0.1239 | 0.043* | |
C4 | 0.4864 (4) | 0.0423 (2) | 0.21105 (18) | 0.0361 (9) | |
H4A | 0.5011 | −0.0239 | 0.2081 | 0.043* | |
C5 | 0.5339 (4) | 0.0834 (2) | 0.26684 (17) | 0.0313 (8) | |
C6 | 0.6104 (4) | 0.0294 (2) | 0.3161 (2) | 0.0400 (9) | |
H6A | 0.6261 | −0.0369 | 0.3138 | 0.048* | |
C7 | 0.6615 (4) | 0.0710 (2) | 0.3665 (2) | 0.0438 (10) | |
H7 | 0.7109 | 0.0335 | 0.3991 | 0.053* | |
C8 | 0.6410 (4) | 0.1706 (2) | 0.3701 (2) | 0.0417 (10) | |
H8 | 0.6794 | 0.1998 | 0.4039 | 0.050* | |
C9 | 0.5654 (4) | 0.2245 (2) | 0.32452 (18) | 0.0348 (9) | |
H9A | 0.5518 | 0.2907 | 0.3277 | 0.042* | |
C10 | 0.5068 (4) | 0.1834 (2) | 0.27248 (17) | 0.0281 (8) | |
C11 | 0.4023 (4) | 0.3453 (2) | 0.22337 (18) | 0.0299 (8) | |
C12 | 0.4491 (4) | 0.4038 (2) | 0.15860 (18) | 0.0306 (8) | |
C13 | 0.4266 (4) | 0.5036 (2) | 0.1525 (2) | 0.0359 (9) | |
H13 | 0.4587 | 0.5406 | 0.1059 | 0.043* | |
C14 | 0.3582 (4) | 0.5458 (2) | 0.2145 (2) | 0.0390 (9) | |
H14 | 0.3453 | 0.6128 | 0.2113 | 0.047* | |
C15 | 0.3060 (4) | 0.4904 (2) | 0.28375 (19) | 0.0329 (8) | |
C16 | 0.2358 (4) | 0.5335 (2) | 0.3490 (2) | 0.0409 (9) | |
H16 | 0.2247 | 0.6005 | 0.3463 | 0.049* | |
C17 | 0.1837 (4) | 0.4805 (2) | 0.4158 (2) | 0.0437 (10) | |
H17 | 0.1380 | 0.5108 | 0.4589 | 0.052* | |
C18 | 0.1983 (4) | 0.3805 (2) | 0.4203 (2) | 0.0401 (9) | |
H18 | 0.1620 | 0.3439 | 0.4666 | 0.048* | |
C19 | 0.2646 (4) | 0.3354 (2) | 0.35836 (18) | 0.0363 (9) | |
H19 | 0.2704 | 0.2682 | 0.3619 | 0.044* | |
C20 | 0.3246 (4) | 0.3891 (2) | 0.28876 (18) | 0.0311 (8) | |
P2 | 0.17925 (11) | 0.83695 (6) | 0.24285 (5) | 0.0371 (3) | |
O5 | 0.0731 (3) | 0.76467 (14) | 0.30098 (11) | 0.0341 (6) | |
O6 | 0.2692 (3) | 0.87165 (14) | 0.29780 (11) | 0.0353 (6) | |
O7 | 0.2716 (3) | 0.77708 (17) | 0.18815 (13) | 0.0511 (7) | |
O8 | 0.1033 (3) | 0.92259 (17) | 0.21483 (16) | 0.0634 (8) | |
C21 | 0.0630 (4) | 0.8089 (2) | 0.42500 (17) | 0.0284 (8) | |
C22 | −0.0051 (4) | 0.7971 (2) | 0.36875 (17) | 0.0303 (8) | |
C23 | −0.1514 (4) | 0.8136 (2) | 0.37639 (19) | 0.0348 (8) | |
H23 | −0.1935 | 0.8025 | 0.3370 | 0.042* | |
C24 | −0.2323 (4) | 0.8456 (2) | 0.44066 (19) | 0.0370 (9) | |
H24 | −0.3316 | 0.8521 | 0.4474 | 0.044* | |
C25 | −0.1688 (4) | 0.8694 (2) | 0.49788 (18) | 0.0319 (8) | |
C26 | −0.2476 (4) | 0.9113 (2) | 0.56202 (19) | 0.0382 (9) | |
H26 | −0.3466 | 0.9211 | 0.5687 | 0.046* | |
C27 | −0.1836 (4) | 0.9380 (2) | 0.6147 (2) | 0.0399 (9) | |
H27 | −0.2386 | 0.9658 | 0.6572 | 0.048* | |
C28 | −0.0368 (4) | 0.9243 (2) | 0.60561 (18) | 0.0375 (9) | |
H28 | 0.0069 | 0.9443 | 0.6415 | 0.045* | |
C29 | 0.0450 (4) | 0.8817 (2) | 0.54447 (17) | 0.0333 (8) | |
H29 | 0.1437 | 0.8724 | 0.5392 | 0.040* | |
C30 | −0.0190 (4) | 0.8520 (2) | 0.48986 (17) | 0.0280 (8) | |
C31 | 0.2156 (4) | 0.7772 (2) | 0.41706 (17) | 0.0286 (8) | |
C32 | 0.3135 (4) | 0.8064 (2) | 0.35202 (18) | 0.0311 (8) | |
C33 | 0.4568 (4) | 0.7743 (2) | 0.3383 (2) | 0.0382 (9) | |
H33 | 0.5198 | 0.7952 | 0.2924 | 0.046* | |
C34 | 0.5044 (4) | 0.7130 (2) | 0.3912 (2) | 0.0417 (9) | |
H34 | 0.6008 | 0.6924 | 0.3821 | 0.050* | |
C35 | 0.4116 (4) | 0.6802 (2) | 0.4595 (2) | 0.0365 (9) | |
C36 | 0.4612 (5) | 0.6162 (3) | 0.5155 (2) | 0.0511 (11) | |
H36 | 0.5588 | 0.5991 | 0.5082 | 0.061* | |
C37 | 0.3703 (6) | 0.5799 (3) | 0.5788 (2) | 0.0527 (12) | |
H37 | 0.4040 | 0.5378 | 0.6154 | 0.063* | |
C38 | 0.2246 (5) | 0.6055 (2) | 0.5896 (2) | 0.0493 (11) | |
H38 | 0.1609 | 0.5784 | 0.6330 | 0.059* | |
C39 | 0.1735 (4) | 0.6688 (2) | 0.53834 (18) | 0.0386 (9) | |
H39 | 0.0756 | 0.6851 | 0.5474 | 0.046* | |
C40 | 0.2647 (4) | 0.7099 (2) | 0.47244 (18) | 0.0314 (8) | |
N5 | −0.0910 (4) | 0.61714 (19) | 0.00186 (15) | 0.0356 (7) | |
H5 | −0.185 (4) | 0.607 (2) | −0.0068 (19) | 0.053* | |
N6 | 0.0366 (4) | 0.8309 (2) | 0.0474 (2) | 0.0598 (11) | |
H6B | −0.052 (4) | 0.867 (3) | 0.048 (3) | 0.090* | |
H6C | 0.107 (6) | 0.842 (3) | 0.060 (3) | 0.090* | |
C51 | 0.0114 (4) | 0.5485 (2) | 0.00753 (17) | 0.0323 (8) | |
C52 | 0.1320 (4) | 0.5762 (2) | 0.02711 (19) | 0.0408 (9) | |
H52 | 0.2071 | 0.5310 | 0.0308 | 0.049* | |
C53 | −0.0831 (4) | 0.7077 (2) | 0.01407 (18) | 0.0374 (9) | |
H53 | −0.1583 | 0.7520 | 0.0084 | 0.045* | |
C54 | 0.0332 (4) | 0.7378 (2) | 0.03484 (19) | 0.0417 (9) | |
C55 | 0.1423 (4) | 0.6689 (2) | 0.0411 (2) | 0.0435 (9) | |
H55 | 0.2237 | 0.6859 | 0.0550 | 0.052* | |
N1 | 0.8043 (3) | 0.2825 (2) | 0.15243 (15) | 0.0362 (7) | |
H1 | 0.738 (4) | 0.326 (2) | 0.1374 (19) | 0.054* | |
N2 | 0.7674 (3) | 0.46415 (19) | 0.17645 (15) | 0.0390 (7) | |
N3 | 0.8985 (4) | 0.0303 (2) | 0.14736 (19) | 0.0504 (9) | |
H3B | 0.951 (5) | −0.015 (3) | 0.169 (2) | 0.076* | |
H3C | 0.836 (5) | 0.007 (3) | 0.121 (2) | 0.076* | |
N4 | 0.8107 (4) | 0.7086 (2) | 0.20931 (18) | 0.0449 (8) | |
H4B | 0.883 (5) | 0.742 (3) | 0.210 (2) | 0.067* | |
H4C | 0.745 (4) | 0.742 (3) | 0.181 (2) | 0.067* | |
C41 | 0.8992 (4) | 0.3158 (2) | 0.18548 (18) | 0.0354 (8) | |
C42 | 0.9989 (4) | 0.2483 (2) | 0.20719 (19) | 0.0410 (9) | |
H42 | 1.0675 | 0.2676 | 0.2302 | 0.049* | |
C43 | 0.9982 (4) | 0.1544 (2) | 0.19537 (19) | 0.0399 (9) | |
H43 | 1.0659 | 0.1102 | 0.2110 | 0.048* | |
C44 | 0.8984 (4) | 0.1225 (2) | 0.16032 (19) | 0.0386 (9) | |
C45 | 0.7994 (4) | 0.1913 (2) | 0.13969 (19) | 0.0374 (9) | |
H45 | 0.7293 | 0.1737 | 0.1169 | 0.045* | |
C46 | 0.8861 (4) | 0.4183 (2) | 0.19335 (18) | 0.0350 (8) | |
C47 | 0.9849 (4) | 0.4665 (2) | 0.21622 (19) | 0.0431 (9) | |
H47 | 1.0661 | 0.4334 | 0.2279 | 0.052* | |
C48 | 0.9633 (4) | 0.5637 (3) | 0.22177 (19) | 0.0438 (9) | |
H48 | 1.0299 | 0.5972 | 0.2371 | 0.053* | |
C49 | 0.8424 (4) | 0.6115 (2) | 0.20454 (18) | 0.0383 (9) | |
C50 | 0.7481 (4) | 0.5573 (2) | 0.1819 (2) | 0.0422 (9) | |
H50 | 0.6661 | 0.5888 | 0.1698 | 0.051* | |
O9 | 0.5612 (3) | 0.7794 (2) | 0.13189 (16) | 0.0515 (8) | |
H9B | 0.547 (5) | 0.758 (3) | 0.093 (3) | 0.077* | |
H9C | 0.471 (5) | 0.787 (3) | 0.155 (3) | 0.077* | |
O10 | 0.7472 (3) | 0.9282 (2) | 0.05583 (17) | 0.0573 (8) | |
H10A | 0.718 (5) | 0.973 (3) | 0.018 (2) | 0.086* | |
H10B | 0.674 (5) | 0.891 (3) | 0.084 (3) | 0.086* | |
O11 | 0.3160 (4) | 0.9211 (2) | 0.04676 (17) | 0.0750 (10) | |
H11A | 0.298 (7) | 0.914 (4) | 0.091 (3) | 0.113* | |
H11B | 0.386 (6) | 0.880 (4) | 0.025 (3) | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0350 (6) | 0.0509 (6) | 0.0303 (5) | −0.0097 (5) | −0.0106 (5) | −0.0004 (4) |
O1 | 0.0283 (15) | 0.0428 (13) | 0.0287 (12) | −0.0061 (11) | −0.0065 (11) | −0.0014 (10) |
O2 | 0.0252 (14) | 0.0410 (12) | 0.0327 (13) | −0.0064 (11) | −0.0069 (11) | −0.0031 (10) |
O3 | 0.0499 (19) | 0.0655 (17) | 0.0447 (15) | −0.0162 (14) | 0.0003 (14) | −0.0212 (13) |
O4 | 0.0422 (18) | 0.0667 (16) | 0.0574 (16) | −0.0151 (14) | −0.0280 (15) | 0.0194 (13) |
C1 | 0.026 (2) | 0.0312 (17) | 0.0271 (17) | −0.0029 (15) | −0.0020 (16) | −0.0048 (14) |
C2 | 0.025 (2) | 0.0344 (18) | 0.0288 (18) | −0.0005 (15) | −0.0065 (16) | −0.0029 (14) |
C3 | 0.040 (2) | 0.0388 (19) | 0.0314 (19) | −0.0115 (17) | −0.0061 (18) | −0.0099 (15) |
C4 | 0.042 (2) | 0.0248 (16) | 0.041 (2) | −0.0055 (16) | −0.0052 (19) | −0.0079 (15) |
C5 | 0.031 (2) | 0.0301 (17) | 0.0308 (18) | −0.0018 (15) | −0.0034 (17) | −0.0024 (14) |
C6 | 0.041 (2) | 0.0291 (17) | 0.049 (2) | 0.0017 (17) | −0.010 (2) | −0.0052 (16) |
C7 | 0.041 (3) | 0.041 (2) | 0.052 (2) | 0.0053 (18) | −0.020 (2) | −0.0009 (17) |
C8 | 0.045 (3) | 0.040 (2) | 0.048 (2) | 0.0001 (18) | −0.027 (2) | −0.0055 (16) |
C9 | 0.038 (2) | 0.0320 (18) | 0.0362 (19) | 0.0016 (16) | −0.0127 (18) | −0.0063 (15) |
C10 | 0.025 (2) | 0.0283 (16) | 0.0283 (18) | −0.0039 (14) | −0.0017 (16) | −0.0023 (13) |
C11 | 0.027 (2) | 0.0318 (17) | 0.0332 (19) | −0.0049 (15) | −0.0119 (17) | −0.0015 (15) |
C12 | 0.022 (2) | 0.0377 (18) | 0.0317 (19) | −0.0008 (15) | −0.0045 (16) | −0.0041 (15) |
C13 | 0.035 (2) | 0.0331 (18) | 0.040 (2) | −0.0065 (16) | −0.0120 (18) | 0.0046 (16) |
C14 | 0.041 (2) | 0.0267 (17) | 0.050 (2) | −0.0053 (16) | −0.013 (2) | −0.0008 (16) |
C15 | 0.029 (2) | 0.0294 (17) | 0.043 (2) | −0.0021 (15) | −0.0121 (18) | −0.0067 (15) |
C16 | 0.042 (3) | 0.0281 (17) | 0.056 (2) | −0.0003 (17) | −0.013 (2) | −0.0131 (17) |
C17 | 0.046 (3) | 0.040 (2) | 0.045 (2) | −0.0021 (18) | −0.004 (2) | −0.0179 (18) |
C18 | 0.038 (2) | 0.042 (2) | 0.039 (2) | −0.0019 (17) | −0.0041 (19) | −0.0093 (16) |
C19 | 0.037 (2) | 0.0325 (18) | 0.040 (2) | −0.0022 (16) | −0.0065 (18) | −0.0073 (16) |
C20 | 0.031 (2) | 0.0306 (17) | 0.0340 (19) | −0.0009 (15) | −0.0119 (17) | −0.0038 (15) |
P2 | 0.0438 (7) | 0.0362 (5) | 0.0303 (5) | −0.0028 (4) | −0.0073 (5) | −0.0013 (4) |
O5 | 0.0390 (16) | 0.0327 (12) | 0.0299 (12) | −0.0019 (11) | −0.0033 (12) | −0.0093 (10) |
O6 | 0.0426 (16) | 0.0315 (12) | 0.0305 (12) | −0.0063 (11) | −0.0058 (12) | −0.0001 (10) |
O7 | 0.0531 (19) | 0.0622 (16) | 0.0335 (14) | −0.0117 (13) | 0.0089 (13) | −0.0198 (12) |
O8 | 0.073 (2) | 0.0460 (15) | 0.0757 (19) | 0.0024 (14) | −0.0383 (18) | 0.0118 (13) |
C21 | 0.028 (2) | 0.0295 (16) | 0.0271 (18) | −0.0028 (15) | −0.0041 (16) | −0.0021 (14) |
C22 | 0.030 (2) | 0.0299 (17) | 0.0287 (18) | −0.0015 (15) | −0.0017 (17) | −0.0061 (14) |
C23 | 0.035 (2) | 0.0379 (19) | 0.034 (2) | −0.0037 (17) | −0.0120 (18) | −0.0040 (15) |
C24 | 0.028 (2) | 0.0383 (19) | 0.043 (2) | 0.0025 (16) | −0.0074 (19) | −0.0049 (16) |
C25 | 0.032 (2) | 0.0264 (17) | 0.0321 (19) | −0.0040 (15) | 0.0027 (17) | −0.0012 (14) |
C26 | 0.036 (2) | 0.0311 (18) | 0.041 (2) | −0.0012 (16) | 0.0020 (19) | −0.0003 (16) |
C27 | 0.041 (3) | 0.0359 (19) | 0.037 (2) | −0.0047 (17) | 0.0067 (19) | −0.0100 (16) |
C28 | 0.049 (3) | 0.0351 (18) | 0.0276 (19) | −0.0079 (17) | −0.0031 (18) | −0.0085 (15) |
C29 | 0.036 (2) | 0.0316 (17) | 0.0339 (19) | 0.0014 (16) | −0.0116 (18) | −0.0067 (14) |
C30 | 0.030 (2) | 0.0238 (16) | 0.0272 (18) | −0.0020 (14) | −0.0003 (16) | −0.0044 (13) |
C31 | 0.031 (2) | 0.0269 (16) | 0.0306 (18) | −0.0024 (15) | −0.0094 (17) | −0.0094 (14) |
C32 | 0.033 (2) | 0.0304 (17) | 0.0310 (19) | −0.0046 (16) | −0.0080 (18) | −0.0061 (14) |
C33 | 0.032 (2) | 0.0375 (19) | 0.045 (2) | −0.0062 (17) | −0.0016 (19) | −0.0120 (16) |
C34 | 0.029 (2) | 0.044 (2) | 0.057 (2) | 0.0032 (17) | −0.015 (2) | −0.0180 (18) |
C35 | 0.041 (2) | 0.0311 (18) | 0.043 (2) | −0.0008 (17) | −0.015 (2) | −0.0155 (16) |
C36 | 0.058 (3) | 0.044 (2) | 0.062 (3) | 0.012 (2) | −0.035 (3) | −0.016 (2) |
C37 | 0.083 (4) | 0.038 (2) | 0.046 (2) | 0.014 (2) | −0.034 (3) | −0.0069 (18) |
C38 | 0.077 (4) | 0.0344 (19) | 0.034 (2) | 0.001 (2) | −0.010 (2) | −0.0041 (16) |
C39 | 0.046 (3) | 0.0368 (19) | 0.034 (2) | 0.0005 (18) | −0.0095 (19) | −0.0091 (16) |
C40 | 0.038 (2) | 0.0281 (17) | 0.0313 (19) | −0.0034 (16) | −0.0104 (18) | −0.0091 (14) |
N5 | 0.036 (2) | 0.0374 (16) | 0.0349 (16) | −0.0057 (15) | −0.0100 (15) | −0.0039 (13) |
N6 | 0.050 (3) | 0.049 (2) | 0.084 (3) | −0.0069 (18) | −0.013 (2) | −0.0250 (19) |
C51 | 0.031 (2) | 0.0375 (18) | 0.0270 (18) | −0.0064 (16) | −0.0027 (16) | −0.0028 (14) |
C52 | 0.033 (2) | 0.044 (2) | 0.047 (2) | −0.0038 (17) | −0.0092 (19) | −0.0076 (17) |
C53 | 0.039 (2) | 0.038 (2) | 0.034 (2) | −0.0024 (17) | −0.0057 (18) | −0.0051 (15) |
C54 | 0.040 (3) | 0.042 (2) | 0.041 (2) | −0.0120 (18) | 0.0005 (19) | −0.0093 (16) |
C55 | 0.034 (2) | 0.050 (2) | 0.049 (2) | −0.0087 (19) | −0.007 (2) | −0.0136 (18) |
N1 | 0.0306 (19) | 0.0391 (17) | 0.0387 (17) | −0.0014 (14) | −0.0097 (15) | −0.0007 (13) |
N2 | 0.033 (2) | 0.0403 (17) | 0.0443 (18) | −0.0010 (14) | −0.0104 (16) | −0.0060 (13) |
N3 | 0.051 (2) | 0.0400 (19) | 0.063 (2) | 0.0045 (16) | −0.0210 (19) | −0.0071 (16) |
N4 | 0.041 (2) | 0.0436 (19) | 0.052 (2) | −0.0053 (15) | −0.0072 (18) | −0.0182 (15) |
C41 | 0.032 (2) | 0.0420 (19) | 0.0311 (19) | −0.0027 (17) | −0.0072 (18) | 0.0008 (15) |
C42 | 0.034 (2) | 0.050 (2) | 0.038 (2) | −0.0044 (18) | −0.0091 (19) | 0.0019 (17) |
C43 | 0.036 (2) | 0.044 (2) | 0.038 (2) | 0.0050 (18) | −0.0098 (19) | 0.0018 (16) |
C44 | 0.030 (2) | 0.046 (2) | 0.037 (2) | −0.0005 (18) | −0.0057 (18) | 0.0000 (16) |
C45 | 0.030 (2) | 0.043 (2) | 0.039 (2) | −0.0024 (17) | −0.0080 (18) | −0.0022 (16) |
C46 | 0.032 (2) | 0.044 (2) | 0.0286 (18) | −0.0074 (17) | −0.0049 (17) | −0.0015 (15) |
C47 | 0.036 (2) | 0.050 (2) | 0.046 (2) | −0.0046 (19) | −0.014 (2) | −0.0046 (17) |
C48 | 0.038 (3) | 0.055 (2) | 0.041 (2) | −0.0087 (19) | −0.0097 (19) | −0.0112 (17) |
C49 | 0.039 (2) | 0.044 (2) | 0.0294 (19) | −0.0045 (18) | −0.0013 (18) | −0.0090 (15) |
C50 | 0.037 (2) | 0.044 (2) | 0.048 (2) | −0.0004 (18) | −0.013 (2) | −0.0095 (17) |
O9 | 0.0481 (19) | 0.0677 (18) | 0.0424 (17) | −0.0006 (16) | −0.0129 (15) | −0.0161 (13) |
O10 | 0.055 (2) | 0.0572 (18) | 0.0596 (19) | −0.0041 (15) | −0.0156 (17) | 0.0004 (14) |
O11 | 0.083 (3) | 0.086 (2) | 0.0466 (18) | 0.0059 (18) | −0.008 (2) | 0.0079 (17) |
P1—O3 | 1.463 (3) | C29—H29 | 0.9400 |
P1—O4 | 1.485 (2) | C31—C32 | 1.372 (5) |
P1—O1 | 1.605 (2) | C31—C40 | 1.439 (4) |
P1—O2 | 1.612 (2) | C32—C33 | 1.402 (5) |
O1—C2 | 1.406 (3) | C33—C34 | 1.356 (5) |
O2—C12 | 1.405 (4) | C33—H33 | 0.9400 |
C1—C2 | 1.375 (4) | C34—C35 | 1.401 (5) |
C1—C10 | 1.430 (4) | C34—H34 | 0.9400 |
C1—C11 | 1.498 (4) | C35—C36 | 1.425 (5) |
C2—C3 | 1.403 (4) | C35—C40 | 1.427 (5) |
C3—C4 | 1.359 (4) | C36—C37 | 1.346 (6) |
C3—H3A | 0.9400 | C36—H36 | 0.9400 |
C4—C5 | 1.412 (4) | C37—C38 | 1.404 (6) |
C4—H4A | 0.9400 | C37—H37 | 0.9400 |
C5—C6 | 1.414 (4) | C38—C39 | 1.366 (4) |
C5—C10 | 1.426 (4) | C38—H38 | 0.9400 |
C6—C7 | 1.352 (5) | C39—C40 | 1.402 (5) |
C6—H6A | 0.9400 | C39—H39 | 0.9400 |
C7—C8 | 1.411 (5) | N5—C53 | 1.333 (4) |
C7—H7 | 0.9400 | N5—C51 | 1.345 (4) |
C8—C9 | 1.362 (4) | N5—H5 | 0.98 (4) |
C8—H8 | 0.9400 | N6—C54 | 1.364 (5) |
C9—C10 | 1.415 (4) | N6—H6B | 0.96 (4) |
C9—H9A | 0.9400 | N6—H6C | 0.81 (5) |
C11—C12 | 1.359 (4) | C51—C52 | 1.397 (5) |
C11—C20 | 1.433 (4) | C51—C51i | 1.472 (6) |
C12—C13 | 1.402 (4) | C52—C55 | 1.377 (5) |
C13—C14 | 1.349 (5) | C52—H52 | 0.9400 |
C13—H13 | 0.9400 | C53—C54 | 1.384 (5) |
C14—C15 | 1.406 (5) | C53—H53 | 0.9400 |
C14—H14 | 0.9400 | C54—C55 | 1.397 (5) |
C15—C16 | 1.407 (5) | C55—H55 | 0.9400 |
C15—C20 | 1.420 (4) | N1—C45 | 1.342 (4) |
C16—C17 | 1.356 (5) | N1—C41 | 1.353 (4) |
C16—H16 | 0.9400 | N1—H1 | 0.92 (4) |
C17—C18 | 1.401 (5) | N2—C50 | 1.324 (4) |
C17—H17 | 0.9400 | N2—C46 | 1.358 (4) |
C18—C19 | 1.365 (5) | N3—C44 | 1.350 (4) |
C18—H18 | 0.9400 | N3—H3B | 0.90 (4) |
C19—C20 | 1.416 (5) | N3—H3C | 0.96 (4) |
C19—H19 | 0.9400 | N4—C49 | 1.389 (4) |
P2—O8 | 1.467 (2) | N4—H4B | 0.87 (4) |
P2—O7 | 1.475 (3) | N4—H4C | 0.97 (3) |
P2—O5 | 1.612 (2) | C41—C42 | 1.395 (4) |
P2—O6 | 1.615 (2) | C41—C46 | 1.464 (5) |
O5—C22 | 1.397 (4) | C42—C43 | 1.368 (5) |
O6—C32 | 1.388 (3) | C42—H42 | 0.9400 |
C21—C22 | 1.377 (4) | C43—C44 | 1.408 (5) |
C21—C30 | 1.434 (4) | C43—H43 | 0.9400 |
C21—C31 | 1.491 (5) | C44—C45 | 1.394 (5) |
C22—C23 | 1.397 (5) | C45—H45 | 0.9400 |
C23—C24 | 1.354 (5) | C46—C47 | 1.383 (5) |
C23—H23 | 0.9400 | C47—C48 | 1.383 (5) |
C24—C25 | 1.417 (5) | C47—H47 | 0.9400 |
C24—H24 | 0.9400 | C48—C49 | 1.389 (5) |
C25—C26 | 1.406 (5) | C48—H48 | 0.9400 |
C25—C30 | 1.430 (5) | C49—C50 | 1.399 (5) |
C26—C27 | 1.363 (5) | C50—H50 | 0.9400 |
C26—H26 | 0.9400 | O9—H9B | 0.85 (4) |
C27—C28 | 1.395 (5) | O9—H9C | 0.88 (5) |
C27—H27 | 0.9400 | O10—H10A | 0.96 (4) |
C28—C29 | 1.380 (5) | O10—H10B | 0.93 (5) |
C28—H28 | 0.9400 | O11—H11A | 0.78 (5) |
C29—C30 | 1.411 (4) | O11—H11B | 0.91 (6) |
O3—P1—O4 | 119.31 (15) | C28—C29—C30 | 120.3 (4) |
O3—P1—O1 | 111.34 (14) | C28—C29—H29 | 119.9 |
O4—P1—O1 | 105.91 (15) | C30—C29—H29 | 119.9 |
O3—P1—O2 | 106.68 (14) | C29—C30—C25 | 118.9 (3) |
O4—P1—O2 | 110.01 (14) | C29—C30—C21 | 121.8 (3) |
O1—P1—O2 | 102.33 (12) | C25—C30—C21 | 119.3 (3) |
C2—O1—P1 | 115.4 (2) | C32—C31—C40 | 117.4 (3) |
C12—O2—P1 | 115.8 (2) | C32—C31—C21 | 119.7 (3) |
C2—C1—C10 | 117.6 (3) | C40—C31—C21 | 122.7 (3) |
C2—C1—C11 | 119.2 (3) | C31—C32—O6 | 118.7 (3) |
C10—C1—C11 | 123.0 (3) | C31—C32—C33 | 122.9 (3) |
C1—C2—C3 | 123.3 (3) | O6—C32—C33 | 118.4 (3) |
C1—C2—O1 | 118.8 (3) | C34—C33—C32 | 119.8 (3) |
C3—C2—O1 | 117.9 (3) | C34—C33—H33 | 120.1 |
C4—C3—C2 | 118.9 (3) | C32—C33—H33 | 120.1 |
C4—C3—H3A | 120.5 | C33—C34—C35 | 120.8 (3) |
C2—C3—H3A | 120.5 | C33—C34—H34 | 119.6 |
C3—C4—C5 | 121.5 (3) | C35—C34—H34 | 119.6 |
C3—C4—H4A | 119.2 | C34—C35—C36 | 121.1 (4) |
C5—C4—H4A | 119.2 | C34—C35—C40 | 119.4 (3) |
C4—C5—C6 | 122.4 (3) | C36—C35—C40 | 119.5 (4) |
C4—C5—C10 | 118.8 (3) | C37—C36—C35 | 120.9 (4) |
C6—C5—C10 | 118.8 (3) | C37—C36—H36 | 119.6 |
C7—C6—C5 | 121.5 (3) | C35—C36—H36 | 119.6 |
C7—C6—H6A | 119.2 | C36—C37—C38 | 119.5 (3) |
C5—C6—H6A | 119.2 | C36—C37—H37 | 120.3 |
C6—C7—C8 | 120.2 (3) | C38—C37—H37 | 120.3 |
C6—C7—H7 | 119.9 | C39—C38—C37 | 121.4 (4) |
C8—C7—H7 | 119.9 | C39—C38—H38 | 119.3 |
C9—C8—C7 | 119.8 (3) | C37—C38—H38 | 119.3 |
C9—C8—H8 | 120.1 | C38—C39—C40 | 121.1 (4) |
C7—C8—H8 | 120.1 | C38—C39—H39 | 119.5 |
C8—C9—C10 | 121.8 (3) | C40—C39—H39 | 119.5 |
C8—C9—H9A | 119.1 | C39—C40—C35 | 117.5 (3) |
C10—C9—H9A | 119.1 | C39—C40—C31 | 123.0 (3) |
C9—C10—C5 | 117.8 (3) | C35—C40—C31 | 119.4 (3) |
C9—C10—C1 | 122.3 (3) | C53—N5—C51 | 123.8 (3) |
C5—C10—C1 | 119.7 (3) | C53—N5—H5 | 110 (2) |
C12—C11—C20 | 117.4 (3) | C51—N5—H5 | 126 (2) |
C12—C11—C1 | 119.0 (3) | C54—N6—H6B | 114 (3) |
C20—C11—C1 | 123.6 (3) | C54—N6—H6C | 113 (4) |
C11—C12—C13 | 123.9 (3) | H6B—N6—H6C | 132 (5) |
C11—C12—O2 | 117.8 (3) | N5—C51—C52 | 116.5 (3) |
C13—C12—O2 | 118.2 (3) | N5—C51—C51i | 118.1 (4) |
C14—C13—C12 | 119.1 (3) | C52—C51—C51i | 125.4 (4) |
C14—C13—H13 | 120.4 | C55—C52—C51 | 120.9 (3) |
C12—C13—H13 | 120.4 | C55—C52—H52 | 119.5 |
C13—C14—C15 | 120.6 (3) | C51—C52—H52 | 119.5 |
C13—C14—H14 | 119.7 | N5—C53—C54 | 121.6 (3) |
C15—C14—H14 | 119.7 | N5—C53—H53 | 119.2 |
C14—C15—C16 | 121.2 (3) | C54—C53—H53 | 119.2 |
C14—C15—C20 | 120.0 (3) | N6—C54—C53 | 119.7 (4) |
C16—C15—C20 | 118.8 (3) | N6—C54—C55 | 123.8 (4) |
C17—C16—C15 | 121.5 (3) | C53—C54—C55 | 116.4 (3) |
C17—C16—H16 | 119.2 | C52—C55—C54 | 120.7 (4) |
C15—C16—H16 | 119.2 | C52—C55—H55 | 119.7 |
C16—C17—C18 | 119.7 (3) | C54—C55—H55 | 119.7 |
C16—C17—H17 | 120.1 | C45—N1—C41 | 125.2 (3) |
C18—C17—H17 | 120.1 | C45—N1—H1 | 118 (2) |
C19—C18—C17 | 120.9 (3) | C41—N1—H1 | 117 (2) |
C19—C18—H18 | 119.5 | C50—N2—C46 | 118.3 (3) |
C17—C18—H18 | 119.5 | C44—N3—H3B | 120 (3) |
C18—C19—C20 | 120.4 (3) | C44—N3—H3C | 124 (2) |
C18—C19—H19 | 119.8 | H3B—N3—H3C | 115 (4) |
C20—C19—H19 | 119.8 | C49—N4—H4B | 115 (3) |
C19—C20—C15 | 118.4 (3) | C49—N4—H4C | 119 (2) |
C19—C20—C11 | 122.6 (3) | H4B—N4—H4C | 114 (4) |
C15—C20—C11 | 118.9 (3) | N1—C41—C42 | 116.0 (3) |
O8—P2—O7 | 119.53 (16) | N1—C41—C46 | 116.2 (3) |
O8—P2—O5 | 112.15 (16) | C42—C41—C46 | 127.7 (3) |
O7—P2—O5 | 105.55 (14) | C43—C42—C41 | 120.9 (3) |
O8—P2—O6 | 106.54 (14) | C43—C42—H42 | 119.6 |
O7—P2—O6 | 109.94 (15) | C41—C42—H42 | 119.6 |
O5—P2—O6 | 101.72 (12) | C42—C43—C44 | 121.5 (3) |
C22—O5—P2 | 118.05 (19) | C42—C43—H43 | 119.2 |
C32—O6—P2 | 120.11 (19) | C44—C43—H43 | 119.2 |
C22—C21—C30 | 117.2 (3) | N3—C44—C45 | 121.8 (4) |
C22—C21—C31 | 120.1 (3) | N3—C44—C43 | 121.9 (3) |
C30—C21—C31 | 122.7 (3) | C45—C44—C43 | 116.4 (3) |
C21—C22—C23 | 123.2 (3) | N1—C45—C44 | 120.0 (3) |
C21—C22—O5 | 119.6 (3) | N1—C45—H45 | 120.0 |
C23—C22—O5 | 117.2 (3) | C44—C45—H45 | 120.0 |
C24—C23—C22 | 119.8 (3) | N2—C46—C47 | 121.5 (3) |
C24—C23—H23 | 120.1 | N2—C46—C41 | 114.6 (3) |
C22—C23—H23 | 120.1 | C47—C46—C41 | 123.8 (3) |
C23—C24—C25 | 120.6 (3) | C48—C47—C46 | 119.6 (3) |
C23—C24—H24 | 119.7 | C48—C47—H47 | 120.2 |
C25—C24—H24 | 119.7 | C46—C47—H47 | 120.2 |
C26—C25—C24 | 122.2 (3) | C47—C48—C49 | 119.5 (4) |
C26—C25—C30 | 118.5 (3) | C47—C48—H48 | 120.3 |
C24—C25—C30 | 119.2 (3) | C49—C48—H48 | 120.3 |
C27—C26—C25 | 121.5 (4) | C48—C49—N4 | 123.6 (3) |
C27—C26—H26 | 119.3 | C48—C49—C50 | 117.2 (3) |
C25—C26—H26 | 119.3 | N4—C49—C50 | 119.2 (3) |
C26—C27—C28 | 120.1 (3) | N2—C50—C49 | 123.9 (3) |
C26—C27—H27 | 119.9 | N2—C50—H50 | 118.0 |
C28—C27—H27 | 119.9 | C49—C50—H50 | 118.0 |
C29—C28—C27 | 120.7 (3) | H9B—O9—H9C | 97 (4) |
C29—C28—H28 | 119.7 | H10A—O10—H10B | 112 (4) |
C27—C28—H28 | 119.7 | H11A—O11—H11B | 113 (5) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.92 (4) | 2.33 (4) | 3.172 (4) | 151 (3) |
N3—H3B···O8ii | 0.90 (4) | 1.97 (4) | 2.830 (4) | 161 (4) |
N3—H3C···O10iii | 0.96 (4) | 2.08 (5) | 3.016 (5) | 164 (4) |
N4—H4C···O9 | 0.97 (3) | 2.18 (4) | 3.124 (5) | 163 (4) |
N5—H5···O4i | 0.98 (4) | 1.61 (4) | 2.581 (4) | 167 (3) |
N6—H6B···O10iv | 0.96 (4) | 2.05 (4) | 3.006 (5) | 173 (4) |
N6—H6C···O11 | 0.81 (5) | 2.34 (5) | 3.078 (6) | 153 (5) |
O9—H9B···O3v | 0.85 (4) | 2.06 (4) | 2.875 (4) | 159 (4) |
O9—H9C···O7 | 0.88 (5) | 1.89 (5) | 2.753 (4) | 164 (4) |
O10—H10A···O11vi | 0.96 (4) | 1.85 (4) | 2.787 (4) | 166 (4) |
O10—H10B···O9 | 0.93 (5) | 1.98 (5) | 2.874 (4) | 162 (4) |
O11—H11B···O3v | 0.91 (6) | 1.99 (5) | 2.817 (4) | 151 (5) |
O11—H11A···O7 | 0.78 (5) | 2.44 (5) | 3.046 (4) | 136 (5) |
O11—H11A···O8 | 0.78 (5) | 2.59 (6) | 3.264 (5) | 147 (6) |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y−1, z; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C10H12N42+·2C10H11N4+·4C20H12O4P−·6H2O |
Mr | 2059.86 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 2402.5 (7) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.56 × 0.04 × 0.03 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.914, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24014, 8570, 4686 |
Rint | 0.098 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.138, 0.99 |
No. of reflections | 8570 |
No. of parameters | 709 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.37 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Crystal Impact, 2006), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.92 (4) | 2.33 (4) | 3.172 (4) | 151 (3) |
N3—H3B···O8i | 0.90 (4) | 1.97 (4) | 2.830 (4) | 161 (4) |
N3—H3C···O10ii | 0.96 (4) | 2.08 (5) | 3.016 (5) | 164 (4) |
N4—H4C···O9 | 0.97 (3) | 2.18 (4) | 3.124 (5) | 163 (4) |
N5—H5···O4iii | 0.98 (4) | 1.61 (4) | 2.581 (4) | 167 (3) |
N6—H6B···O10iv | 0.96 (4) | 2.05 (4) | 3.006 (5) | 173 (4) |
N6—H6C···O11 | 0.81 (5) | 2.34 (5) | 3.078 (6) | 153 (5) |
O9—H9B···O3v | 0.85 (4) | 2.06 (4) | 2.875 (4) | 159 (4) |
O9—H9C···O7 | 0.88 (5) | 1.89 (5) | 2.753 (4) | 164 (4) |
O10—H10A···O11vi | 0.96 (4) | 1.85 (4) | 2.787 (4) | 166 (4) |
O10—H10B···O9 | 0.93 (5) | 1.98 (5) | 2.874 (4) | 162 (4) |
O11—H11B···O3v | 0.91 (6) | 1.99 (5) | 2.817 (4) | 151 (5) |
O11—H11A···O7 | 0.78 (5) | 2.44 (5) | 3.046 (4) | 136 (5) |
O11—H11A···O8 | 0.78 (5) | 2.59 (6) | 3.264 (5) | 147 (6) |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y−1, z; (iii) −x, −y+1, −z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) −x+1, −y+2, −z. |
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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).