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organic compounds
The cation, anion and water molecules of the title compound, 2C5H6NO+·C10H6O6S22-·2H2O, interact via hydrogen bonds, giving rise to a tight three-dimensional network structure. Two independent anions both lie on centers of inversion, and the asymmetric unit consists of two half-anions, two independent cations and two independent water molecules.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032313/bt6557sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032313/bt6557Isup2.hkl |
CCDC reference: 262459
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.123
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT110_ALERT_2_B ADDSYM Detects Potential Lattice Centering or Halving . ? PLAT417_ALERT_2_B Short Inter D-H..H-D H2W2 .. H7O .. 2.08 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.10 PLAT417_ALERT_2_C Short Inter D-H..H-D H1W2 .. H8O .. 2.10 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT736_ALERT_1_C H...A Calc 2.06(3), Rep 2.060(10) ...... 3.00 su-Rat H2# -O5 1.555 4.566
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(2-hydroxypyridinium) naphthalene-1,5-disulfonate dihydrate top
Crystal data top
2C5H6NO+·C10H6O6S22−·2H2O | F(000) = 1072 |
Mr = 514.52 | Dx = 1.525 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 16290 reflections |
a = 14.740 (3) Å | θ = 3.3–27.4° |
b = 10.883 (2) Å | µ = 0.30 mm−1 |
c = 14.075 (3) Å | T = 295 K |
β = 96.91 (3)° | Prism, colorless |
V = 2241.7 (8) Å3 | 0.42 × 0.31 × 0.24 mm |
Z = 4 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 5082 independent reflections |
Radiation source: fine-focus sealed tube | 3742 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.797, Tmax = 0.932 | k = −14→12 |
20659 measured reflections | l = −18→18 |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0679P)2 + 0.5447P] where P = (Fo2 + 2Fc2)/3 |
5082 reflections | (Δ/σ)max = 0.001 |
339 parameters | Δρmax = 0.44 e Å−3 |
10 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.86407 (3) | 0.56595 (5) | 0.78973 (3) | 0.0396 (1) | |
S2 | 0.63667 (3) | 0.44727 (5) | 0.21166 (3) | 0.0384 (1) | |
O1 | 0.8459 (1) | 0.4414 (2) | 0.7560 (1) | 0.0586 (4) | |
O2 | 0.9377 (1) | 0.6254 (2) | 0.7484 (1) | 0.0569 (4) | |
O3 | 0.7830 (1) | 0.6420 (2) | 0.7813 (1) | 0.0549 (4) | |
O4 | 0.7332 (1) | 0.4222 (2) | 0.2218 (1) | 0.0602 (5) | |
O5 | 0.5859 (1) | 0.3417 (1) | 0.2418 (1) | 0.0509 (4) | |
O6 | 0.6149 (1) | 0.5608 (2) | 0.2566 (1) | 0.0589 (4) | |
O7 | 0.8994 (1) | 0.6142 (2) | 0.4897 (1) | 0.0512 (4) | |
O8 | 0.6127 (1) | 0.3574 (2) | 0.5020 (1) | 0.0518 (4) | |
O1w | 0.6684 (1) | 0.3768 (2) | 0.6800 (1) | 0.0638 (5) | |
O2w | 0.8328 (1) | 0.6143 (2) | 0.3171 (1) | 0.0651 (5) | |
N1 | 1.0234 (1) | 0.6533 (2) | 0.5908 (1) | 0.0420 (4) | |
N2 | 0.4883 (1) | 0.3353 (2) | 0.3961 (1) | 0.0414 (4) | |
C1 | 0.9018 (1) | 0.5562 (2) | 0.9147 (1) | 0.0319 (4) | |
C2 | 0.8464 (1) | 0.6035 (2) | 0.9762 (1) | 0.0388 (4) | |
C3 | 0.8727 (1) | 0.5998 (2) | 1.0752 (1) | 0.0423 (5) | |
C4 | 0.9534 (1) | 0.5501 (2) | 1.1116 (1) | 0.0377 (4) | |
C5 | 1.0131 (1) | 0.4988 (2) | 1.0504 (1) | 0.0302 (4) | |
C6 | 0.6022 (1) | 0.4623 (2) | 0.0866 (1) | 0.0307 (4) | |
C7 | 0.6659 (1) | 0.4403 (2) | 0.0262 (1) | 0.0379 (4) | |
C8 | 0.6426 (1) | 0.4502 (2) | −0.0731 (1) | 0.0412 (5) | |
C9 | 0.5568 (1) | 0.4811 (2) | −0.1107 (1) | 0.0362 (4) | |
C10 | 0.4887 (1) | 0.5046 (2) | −0.0507 (1) | 0.0292 (4) | |
C11 | 0.9853 (1) | 0.6474 (2) | 0.5005 (2) | 0.0392 (4) | |
C12 | 1.0378 (2) | 0.6738 (2) | 0.4277 (2) | 0.0493 (5) | |
C13 | 1.1275 (2) | 0.7024 (2) | 0.4521 (2) | 0.0576 (6) | |
C14 | 1.1654 (2) | 0.7050 (2) | 0.5471 (2) | 0.0575 (6) | |
C15 | 1.1115 (2) | 0.6814 (2) | 0.6156 (2) | 0.0505 (5) | |
C16 | 0.5239 (1) | 0.3432 (2) | 0.4878 (1) | 0.0375 (4) | |
C17 | 0.4659 (1) | 0.3384 (2) | 0.5579 (1) | 0.0454 (5) | |
C18 | 0.3748 (2) | 0.3278 (2) | 0.5307 (2) | 0.0538 (6) | |
C19 | 0.3399 (2) | 0.3211 (2) | 0.4347 (2) | 0.0553 (6) | |
C20 | 0.3983 (2) | 0.3245 (2) | 0.3686 (2) | 0.0494 (5) | |
H1n | 0.990 (1) | 0.635 (2) | 0.635 (1) | 0.06 (1)* | |
H2n | 0.525 (1) | 0.341 (2) | 0.355 (1) | 0.06 (1)* | |
H7o | 0.876 (2) | 0.615 (3) | 0.431 (1) | 0.08 (1)* | |
H8o | 0.631 (2) | 0.362 (3) | 0.562 (1) | 0.07 (1)* | |
H1w1 | 0.720 (1) | 0.405 (2) | 0.703 (2) | 0.07 (1)* | |
H1w2 | 0.661 (2) | 0.307 (2) | 0.705 (2) | 0.10 (1)* | |
H2w1 | 0.797 (1) | 0.559 (1) | 0.293 (2) | 0.07 (1)* | |
H2w2 | 0.810 (2) | 0.685 (1) | 0.304 (2) | 0.06 (1)* | |
H2 | 0.7908 | 0.6385 | 0.9523 | 0.047* | |
H3 | 0.8340 | 0.6321 | 1.1164 | 0.051* | |
H4 | 0.9700 | 0.5494 | 1.1775 | 0.045* | |
H7 | 0.7251 | 0.4186 | 0.0508 | 0.046* | |
H8 | 0.6867 | 0.4354 | −0.1136 | 0.049* | |
H9 | 0.5426 | 0.4868 | −0.1768 | 0.043* | |
H12 | 1.0125 | 0.6720 | 0.3640 | 0.059* | |
H13 | 1.1638 | 0.7205 | 0.4043 | 0.069* | |
H14 | 1.2271 | 0.7228 | 0.5632 | 0.069* | |
H15 | 1.1353 | 0.6846 | 0.6798 | 0.061* | |
H17 | 0.4888 | 0.3423 | 0.6224 | 0.054* | |
H18 | 0.3349 | 0.3249 | 0.5771 | 0.065* | |
H19 | 0.2773 | 0.3144 | 0.4166 | 0.066* | |
H20 | 0.3765 | 0.3194 | 0.3039 | 0.059* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0382 (3) | 0.0513 (3) | 0.0265 (2) | −0.0043 (2) | −0.0072 (2) | 0.0034 (1) |
S2 | 0.0375 (3) | 0.0512 (3) | 0.0248 (2) | −0.0028 (2) | −0.0035 (2) | 0.0000 (2) |
O1 | 0.068 (1) | 0.059 (1) | 0.043 (1) | −0.004 (1) | −0.0173 (7) | −0.009 (1) |
O2 | 0.053 (1) | 0.084 (1) | 0.033 (1) | −0.010 (1) | 0.0032 (7) | 0.014 (1) |
O3 | 0.046 (1) | 0.069 (1) | 0.045 (1) | 0.007 (1) | −0.0142 (7) | 0.008 (1) |
O4 | 0.041 (1) | 0.095 (1) | 0.042 (1) | 0.006 (1) | −0.0075 (7) | 0.006 (1) |
O5 | 0.064 (1) | 0.059 (1) | 0.030 (1) | −0.010 (1) | 0.0069 (7) | 0.006 (1) |
O6 | 0.077 (1) | 0.060 (1) | 0.036 (1) | 0.001 (1) | −0.0066 (7) | −0.016 (1) |
O7 | 0.043 (1) | 0.059 (1) | 0.050 (1) | −0.007 (1) | −0.0039 (7) | 0.002 (1) |
O8 | 0.040 (1) | 0.068 (1) | 0.047 (1) | −0.002 (1) | 0.0008 (7) | 0.004 (1) |
O1w | 0.064 (1) | 0.070 (1) | 0.052 (1) | −0.020 (1) | −0.013 (1) | 0.005 (1) |
O2w | 0.069 (1) | 0.062 (1) | 0.056 (1) | −0.016 (1) | −0.023 (1) | 0.001 (1) |
N1 | 0.045 (1) | 0.045 (1) | 0.036 (1) | 0.001 (1) | 0.004 (1) | 0.000 (1) |
N2 | 0.046 (1) | 0.047 (1) | 0.031 (1) | −0.003 (1) | 0.005 (1) | 0.001 (1) |
C1 | 0.031 (1) | 0.039 (1) | 0.025 (1) | −0.006 (1) | −0.003 (1) | 0.002 (1) |
C2 | 0.032 (1) | 0.048 (1) | 0.036 (1) | 0.001 (1) | 0.002 (1) | 0.004 (1) |
C3 | 0.039 (1) | 0.054 (1) | 0.035 (1) | 0.006 (1) | 0.009 (1) | 0.000 (1) |
C4 | 0.040 (1) | 0.049 (1) | 0.025 (1) | −0.001 (1) | 0.004 (1) | 0.000 (1) |
C5 | 0.030 (1) | 0.035 (1) | 0.025 (1) | −0.006 (1) | 0.000 (1) | 0.002 (1) |
C6 | 0.032 (1) | 0.035 (1) | 0.025 (1) | −0.002 (1) | 0.002 (1) | 0.000 (1) |
C7 | 0.029 (1) | 0.050 (1) | 0.034 (1) | 0.001 (1) | 0.002 (1) | 0.001 (1) |
C8 | 0.034 (1) | 0.059 (1) | 0.032 (1) | 0.003 (1) | 0.011 (1) | −0.002 (1) |
C9 | 0.038 (1) | 0.048 (1) | 0.023 (1) | 0.000 (1) | 0.006 (1) | 0.000 (1) |
C10 | 0.031 (1) | 0.032 (1) | 0.025 (1) | −0.004 (1) | 0.003 (1) | −0.002 (1) |
C11 | 0.041 (1) | 0.035 (1) | 0.040 (1) | 0.002 (1) | 0.000 (1) | −0.001 (1) |
C12 | 0.060 (1) | 0.053 (1) | 0.034 (1) | 0.001 (1) | 0.001 (1) | 0.000 (1) |
C13 | 0.054 (1) | 0.066 (2) | 0.056 (1) | −0.004 (1) | 0.020 (1) | −0.002 (1) |
C14 | 0.039 (1) | 0.065 (2) | 0.067 (2) | −0.007 (1) | 0.003 (1) | −0.007 (1) |
C15 | 0.051 (1) | 0.052 (1) | 0.045 (1) | 0.001 (1) | −0.009 (1) | −0.006 (1) |
C16 | 0.040 (1) | 0.035 (1) | 0.037 (1) | −0.001 (1) | 0.002 (1) | 0.001 (1) |
C17 | 0.049 (1) | 0.056 (1) | 0.031 (1) | −0.001 (1) | 0.003 (1) | −0.003 (1) |
C18 | 0.047 (1) | 0.070 (2) | 0.046 (1) | −0.007 (1) | 0.012 (1) | −0.004 (1) |
C19 | 0.042 (1) | 0.065 (2) | 0.056 (1) | −0.010 (1) | −0.001 (1) | −0.003 (1) |
C20 | 0.055 (1) | 0.054 (1) | 0.036 (1) | −0.009 (1) | −0.006 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
S1—O1 | 1.450 (2) | C12—C13 | 1.361 (3) |
S1—O2 | 1.444 (2) | C13—C14 | 1.386 (3) |
S1—O3 | 1.447 (2) | C14—C15 | 1.346 (3) |
S1—C1 | 1.784 (2) | C16—C17 | 1.383 (3) |
S2—O4 | 1.438 (2) | C17—C18 | 1.357 (3) |
S2—O5 | 1.462 (2) | C18—C19 | 1.388 (3) |
S2—O6 | 1.441 (2) | C19—C20 | 1.342 (3) |
S2—C6 | 1.780 (2) | O7—H7o | 0.86 (1) |
O7—C11 | 1.307 (2) | O8—H8o | 0.85 (1) |
O8—C16 | 1.308 (2) | O1w—H1w1 | 0.85 (1) |
N1—C11 | 1.328 (3) | O1w—H1w2 | 0.85 (1) |
N1—C15 | 1.339 (3) | O2w—H2w1 | 0.85 (1) |
N2—C16 | 1.336 (2) | O2w—H2w2 | 0.85 (1) |
N2—C20 | 1.341 (3) | N1—H1n | 0.86 (1) |
C1—C2 | 1.360 (3) | N2—H2n | 0.85 (1) |
C1—C5i | 1.423 (2) | C2—H2 | 0.93 |
C2—C3 | 1.402 (3) | C3—H3 | 0.93 |
C3—C4 | 1.351 (3) | C4—H4 | 0.93 |
C4—C5 | 1.417 (2) | C7—H7 | 0.93 |
C5—C1i | 1.423 (2) | C8—H8 | 0.93 |
C5—C5i | 1.426 (3) | C9—H9 | 0.93 |
C6—C7 | 1.363 (2) | C12—H12 | 0.93 |
C6—C10ii | 1.420 (2) | C13—H13 | 0.93 |
C7—C8 | 1.402 (3) | C14—H14 | 0.93 |
C8—C9 | 1.353 (3) | C15—H15 | 0.93 |
C9—C10 | 1.412 (2) | C17—H17 | 0.93 |
C10—C6ii | 1.420 (2) | C18—H18 | 0.93 |
C10—C10ii | 1.429 (3) | C19—H19 | 0.93 |
C11—C12 | 1.387 (3) | C20—H20 | 0.93 |
O1—S1—O2 | 113.9 (1) | C18—C17—C16 | 118.5 (2) |
O1—S1—O3 | 112.9 (1) | C17—C18—C19 | 121.2 (2) |
O1—S1—C1 | 106.9 (1) | C20—C19—C18 | 118.7 (2) |
O2—S1—O3 | 111.3 (1) | N2—C20—C19 | 119.7 (2) |
O2—S1—C1 | 105.3 (1) | C11—O7—H7o | 112 (2) |
O3—S1—C1 | 105.8 (1) | C16—O8—H8o | 111 (2) |
O4—S2—O5 | 110.9 (1) | H1w1—O1w—H1w2 | 108 (2) |
O4—S2—O6 | 112.9 (1) | H2w1—O2w—H2w2 | 110 (2) |
O4—S2—C6 | 106.1 (1) | C11—N1—C15 | 123.2 (2) |
O5—S2—O6 | 113.5 (1) | C11—N1—H1n | 118 (2) |
O5—S2—C6 | 105.3 (1) | C15—N1—H1n | 119 (2) |
O6—S2—C6 | 107.6 (1) | C16—N2—H2n | 117 (2) |
C16—N2—C20 | 123.1 (2) | C20—N2—H2n | 120 (2) |
C2—C1—C5i | 120.8 (2) | C1—C2—H2 | 119.8 |
C2—C1—S1 | 117.7 (1) | C3—C2—H2 | 119.8 |
C5i—C1—S1 | 121.5 (1) | C4—C3—H3 | 119.5 |
C1—C2—C3 | 120.5 (2) | C2—C3—H3 | 119.5 |
C4—C3—C2 | 120.9 (2) | C3—C4—H4 | 119.7 |
C3—C4—C5 | 120.7 (2) | C5—C4—H4 | 119.7 |
C4—C5—C1i | 122.8 (2) | C6—C7—H7 | 119.9 |
C4—C5—C5i | 119.0 (2) | C8—C7—H7 | 119.9 |
C1i—C5—C5i | 118.2 (2) | C9—C8—H8 | 119.5 |
C7—C6—C10ii | 120.9 (2) | C7—C8—H8 | 119.5 |
C7—C6—S2 | 117.7 (1) | C8—C9—H9 | 119.7 |
C10ii—C6—S2 | 121.4 (1) | C10—C9—H9 | 119.7 |
C6—C7—C8 | 120.2 (2) | C13—C12—H12 | 120.9 |
C9—C8—C7 | 121.0 (2) | C11—C12—H12 | 120.9 |
C8—C9—C10 | 120.6 (2) | C12—C13—H13 | 119.5 |
C9—C10—C6ii | 122.7 (2) | C14—C13—H13 | 119.5 |
C9—C10—C10ii | 119.2 (2) | C15—C14—H14 | 120.6 |
C6ii—C10—C10ii | 118.1 (2) | C13—C14—H14 | 120.6 |
O7—C11—N1 | 114.7 (2) | N1—C15—H15 | 120.2 |
O7—C11—C12 | 126.2 (2) | C14—C15—H15 | 120.2 |
N1—C11—C12 | 119.1 (2) | C18—C17—H17 | 120.7 |
C13—C12—C11 | 118.2 (2) | C16—C17—H17 | 120.7 |
C12—C13—C14 | 121.0 (2) | C17—C18—H18 | 119.4 |
C15—C14—C13 | 118.9 (2) | C19—C18—H18 | 119.4 |
N1—C15—C14 | 119.6 (2) | C20—C19—H19 | 120.6 |
O8—C16—N2 | 115.1 (2) | C18—C19—H19 | 120.6 |
O8—C16—C17 | 126.1 (2) | N2—C20—H20 | 120.1 |
N2—C16—C17 | 118.8 (2) | C19—C20—H20 | 120.1 |
O2—S1—C1—C2 | 125.9 (2) | C6—C7—C8—C9 | −0.3 (3) |
O3—S1—C1—C2 | 8.0 (2) | C7—C8—C9—C10 | 0.3 (3) |
O1—S1—C1—C2 | −112.6 (2) | C8—C9—C10—C6ii | 179.8 (2) |
O2—S1—C1—C5i | −53.9 (2) | C8—C9—C10—C10ii | −0.1 (3) |
O3—S1—C1—C5i | −171.9 (1) | C15—N1—C11—O7 | 177.6 (2) |
O1—S1—C1—C5i | 67.6 (2) | C15—N1—C11—C12 | −1.3 (3) |
C5i—C1—C2—C3 | 0.5 (3) | O7—C11—C12—C13 | −177.5 (2) |
S1—C1—C2—C3 | −179.3 (2) | N1—C11—C12—C13 | 1.3 (3) |
C1—C2—C3—C4 | 0.4 (3) | C11—C12—C13—C14 | 0.1 (4) |
C2—C3—C4—C5 | −0.8 (3) | C12—C13—C14—C15 | −1.5 (4) |
C3—C4—C5—C1i | −179.1 (2) | C11—N1—C15—C14 | −0.1 (3) |
C3—C4—C5—C5i | 0.3 (3) | C13—C14—C15—N1 | 1.5 (4) |
O4—S2—C6—C7 | 4.4 (2) | C20—N2—C16—O8 | −177.8 (2) |
O6—S2—C6—C7 | 125.5 (2) | C20—N2—C16—C17 | 1.0 (3) |
O5—S2—C6—C7 | −113.2 (2) | O8—C16—C17—C18 | 177.6 (2) |
O4—S2—C6—C10ii | −175.9 (2) | N2—C16—C17—C18 | −1.1 (3) |
O6—S2—C6—C10ii | −54.8 (2) | C16—C17—C18—C19 | 0.4 (4) |
O5—S2—C6—C10ii | 66.5 (2) | C17—C18—C19—C20 | 0.4 (4) |
C10ii—C6—C7—C8 | 0.1 (3) | C16—N2—C20—C19 | −0.1 (3) |
S2—C6—C7—C8 | 179.8 (2) | C18—C19—C20—N2 | −0.6 (4) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7o···O2w | 0.86 (1) | 1.65 (1) | 2.509 (2) | 179 (3) |
O8—H8o···O1w | 0.85 (1) | 1.70 (1) | 2.550 (2) | 178 (3) |
O1w—H1w1···O1 | 0.85 (1) | 1.95 (1) | 2.794 (2) | 170 (2) |
O1w—H1w2···O5iii | 0.85 (1) | 2.06 (1) | 2.854 (3) | 154 (2) |
O2w—H2w1···O4 | 0.85 (1) | 1.97 (1) | 2.803 (2) | 168 (3) |
O2w—H2w2···O3iv | 0.85 (1) | 1.95 (1) | 2.782 (3) | 168 (2) |
N1—H1n···O2 | 0.86 (1) | 1.86 (1) | 2.700 (2) | 165 (2) |
N2—H2n···O5 | 0.85 (1) | 1.92 (1) | 2.748 (2) | 167 (2) |
Symmetry codes: (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z−1/2. |
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