Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801009758/na6086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801009758/na6086Isup2.hkl |
CCDC reference: 170769
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.147
- Data-to-parameter ratio = 6.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
DIFF_012 Alert A _diffrn_reflns_av_R_equivalents is missing R factor for symmetry-equivalent intensities. The following tests will not be performed RINTA
Alert Level C:
PLAT_302 Alert C Anion/Solvent Disorder ....................... 7.00 Perc. PLAT_354 Alert C Short O-H Bond (0.82A) OW1 - HW2 = 0.68 Ang. PLAT_354 Alert C Short O-H Bond (0.82A) OW2 - HW3 = 0.64 Ang. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C6 H14 N3 O7.5 S1 Atom count from _chemical_formula_moiety:C12 H28 N6 O15 S2 FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C6 H14 N3 O7.5 S1 Atom count from the _atom_site data: C6 H14 N3 O7.515 S1 REFLT_03 From the CIF: _diffrn_reflns_theta_max 67.95 From the CIF: _reflns_number_total 2303 Count of symmetry unique reflns 2144 Completeness (_total/calc) 107.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 159 Fraction of Friedel pairs measured 0.074 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
The title compound, (I), was crystallized in aqueous solution of DL-histidine and sulfuric acid by slow evaporation. The density of the sample was measured by flotation technique using a mixture of carbon tetrachloride and xylene.
One of the O atoms (O8) of the sulfate anion is disordered and the site-occupation factor of O8 and O8' are 0.74 (2) and 0.29 (2), respectively. The H atoms of the water molecules were located from difference Fourier maps and refined, leading to short O—H bonds, since the H atoms of the water molecules cannot be fixed by HFIX constraints, while all other H atoms were fixed by geometric restraints using HFIX and were allowed to ride on the preceding atom.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structures of the two independent cations showing the atomic numbering scheme and 50% probability displacement ellipsoids (Johnson, 1976). |
2C6H11N3O22+·2SO42−·3H2O | Z = 2 |
Mr = 280.26 | F(000) = 294 |
Triclinic, P1 | Dx = 1.572 Mg m−3 Dm = 1.568 Mg m−3 Dm measured by flotation method |
a = 8.3400 (13) Å | Cu Kα radiation, λ = 1.5418 Å |
b = 8.9291 (11) Å | Cell parameters from 25 reflections |
c = 10.724 (2) Å | θ = 15.2–23.8° |
α = 102.576 (13)° | µ = 2.81 mm−1 |
β = 107.704 (15)° | T = 293 K |
γ = 119.667 (11)° | Needles, colorless |
V = 592.03 (16) Å3 | 0.5 × 0.3 × 0.15 mm |
Enraf-Nonius sealed-tube diffractometer | 2280 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | θmax = 68.0°, θmin = 4.8° |
Graphite monochromator | h = 0→10 |
ω–2θ scans | k = −10→9 |
Absorption correction: ψ scan (North et al., 1968) | l = −12→12 |
Tmin = 0.418, Tmax = 0.656 | 25 standard reflections every 3 reflections |
2303 measured reflections | intensity decay: none |
2303 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.1061P)2 + 0.447P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.148 | (Δ/σ)max = 0.014 |
S = 1.05 | Δρmax = 0.79 e Å−3 |
2303 reflections | Δρmin = −0.48 e Å−3 |
346 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.042 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (3) |
2C6H11N3O22+·2SO42−·3H2O | γ = 119.667 (11)° |
Mr = 280.26 | V = 592.03 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3400 (13) Å | Cu Kα radiation |
b = 8.9291 (11) Å | µ = 2.81 mm−1 |
c = 10.724 (2) Å | T = 293 K |
α = 102.576 (13)° | 0.5 × 0.3 × 0.15 mm |
β = 107.704 (15)° |
Enraf-Nonius sealed-tube diffractometer | 2303 independent reflections |
Absorption correction: ψ scan (North et al., 1968) | 2280 reflections with I > 2σ(I) |
Tmin = 0.418, Tmax = 0.656 | 25 standard reflections every 3 reflections |
2303 measured reflections | intensity decay: none |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | Δρmax = 0.79 e Å−3 |
S = 1.05 | Δρmin = −0.48 e Å−3 |
2303 reflections | Absolute structure: Flack (1983) |
346 parameters | Absolute structure parameter: 0.03 (3) |
4 restraints |
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 | Occ. (<1) | |
S1 | 0.03763 (15) | 0.60380 (13) | 0.40015 (11) | 0.0331 (3) | |
O1 | 0.0732 (9) | 0.7682 (8) | 0.3749 (7) | 0.0662 (16) | |
O2 | −0.0783 (7) | 0.5676 (6) | 0.4815 (5) | 0.0468 (10) | |
O3 | 0.2439 (8) | 0.6471 (9) | 0.4826 (7) | 0.0680 (15) | |
O4 | −0.0875 (10) | 0.4308 (8) | 0.2637 (6) | 0.0705 (15) | |
S2 | 0.40467 (19) | 0.69101 (18) | 0.03876 (15) | 0.0453 (4) | |
O5 | 0.4892 (16) | 0.7160 (10) | −0.0605 (8) | 0.111 (3) | |
O6 | 0.3650 (10) | 0.5184 (8) | 0.0550 (7) | 0.0674 (15) | |
O7 | 0.5773 (14) | 0.8652 (10) | 0.1742 (8) | 0.103 (3) | |
O8 | 0.2146 (17) | 0.674 (2) | −0.027 (2) | 0.148 (9) | 0.74 (2) |
O8' | 0.269 (3) | 0.723 (2) | 0.1008 (18) | 0.053 (6) | 0.29 (2) |
O1A | 0.4086 (7) | 0.3484 (6) | 0.3882 (4) | 0.0490 (10) | |
O1B | 0.4502 (10) | 0.3011 (8) | 0.5873 (5) | 0.0653 (15) | |
H1B | 0.4379 | 0.3866 | 0.6128 | 0.098* | |
C11 | 0.4482 (9) | 0.2748 (8) | 0.4639 (6) | 0.0393 (12) | |
C12 | 0.4990 (9) | 0.1391 (7) | 0.4179 (6) | 0.0330 (11) | |
H12 | 0.3761 | 0.0081 | 0.3857 | 0.040* | |
N11 | 0.5364 (8) | 0.1485 (6) | 0.2909 (5) | 0.0394 (10) | |
H11A | 0.5661 | 0.0681 | 0.2633 | 0.059* | |
H11B | 0.6442 | 0.2679 | 0.3170 | 0.059* | |
H11C | 0.4210 | 0.1149 | 0.2169 | 0.059* | |
C13 | 0.6873 (11) | 0.1832 (9) | 0.5451 (6) | 0.0487 (15) | |
H13A | 0.8101 | 0.3118 | 0.5759 | 0.058* | |
H13B | 0.6590 | 0.1837 | 0.6264 | 0.058* | |
C14 | 0.7404 (9) | 0.0479 (8) | 0.5140 (7) | 0.0405 (13) | |
N12 | 0.6058 (8) | −0.1443 (7) | 0.4802 (6) | 0.0421 (11) | |
H12A | 0.4835 | −0.2014 | 0.4748 | 0.051* | |
C15 | 0.6976 (11) | −0.2250 (9) | 0.4576 (9) | 0.0541 (17) | |
H15 | 0.6392 | −0.3543 | 0.4302 | 0.065* | |
N13 | 0.8798 (12) | −0.0955 (10) | 0.4799 (10) | 0.073 (2) | |
H13 | 0.9685 | −0.1151 | 0.4728 | 0.087* | |
C16 | 0.9155 (12) | 0.0787 (11) | 0.5164 (11) | 0.066 (2) | |
H16 | 1.0369 | 0.1949 | 0.5385 | 0.079* | |
O2A | 1.2077 (7) | 0.1007 (7) | 1.0362 (5) | 0.0535 (11) | |
O2B | 0.8902 (8) | −0.1261 (8) | 0.8411 (5) | 0.0694 (15) | |
H2B | 0.9554 | −0.1575 | 0.8136 | 0.104* | |
C21 | 1.0216 (9) | 0.0283 (8) | 0.9656 (6) | 0.0365 (12) | |
C22 | 0.9210 (8) | 0.1188 (8) | 1.0076 (6) | 0.0339 (11) | |
H22 | 0.8134 | 0.0320 | 1.0281 | 0.041* | |
N21 | 1.0880 (7) | 0.3008 (6) | 1.1423 (4) | 0.0359 (9) | |
H21A | 1.0329 | 0.3567 | 1.1697 | 0.054* | |
H21B | 1.1886 | 0.3790 | 1.1255 | 0.054* | |
H21C | 1.1430 | 0.2763 | 1.2129 | 0.054* | |
C23 | 0.8163 (10) | 0.1520 (9) | 0.8836 (6) | 0.0404 (12) | |
H23A | 0.9186 | 0.2224 | 0.8541 | 0.048* | |
H23B | 0.7009 | 0.0280 | 0.8004 | 0.048* | |
C24 | 0.7332 (9) | 0.2588 (8) | 0.9200 (6) | 0.0359 (11) | |
N22 | 0.8443 (9) | 0.4537 (8) | 0.9632 (7) | 0.0478 (12) | |
H22A | 0.9671 | 0.5270 | 0.9716 | 0.057* | |
C25 | 0.7365 (12) | 0.5110 (10) | 0.9894 (9) | 0.0557 (17) | |
H25 | 0.7802 | 0.6369 | 1.0203 | 0.067* | |
N23 | 0.5561 (9) | 0.3623 (8) | 0.9650 (7) | 0.0523 (13) | |
H23 | 0.4585 | 0.3650 | 0.9742 | 0.063* | |
C26 | 0.5496 (10) | 0.2023 (10) | 0.9223 (8) | 0.0492 (14) | |
H26 | 0.4403 | 0.0781 | 0.8992 | 0.059* | |
OW1 | 0.3466 (10) | 0.5063 (7) | 0.6637 (6) | 0.0544 (12) | |
HW1 | 0.361 (13) | 0.526 (12) | 0.752 (10) | 0.06 (2)* | |
HW2 | 0.287 (11) | 0.529 (10) | 0.626 (8) | 0.034 (19)* | |
OW2 | 0.0771 (12) | 0.7555 (12) | 0.7679 (7) | 0.083 (2) | |
HW3 | 0.077 (11) | 0.716 (9) | 0.710 (8) | 0.033 (17)* | |
HW4 | 0.109 (17) | 0.707 (14) | 0.819 (12) | 0.08 (3)* | |
OW3 | 0.9820 (10) | 0.9524 (10) | 0.2202 (8) | 0.092 (2) | |
HW5 | 1.0135 | 0.8875 | 0.2747 | 0.050* | |
HW6 | 0.8465 | 0.9231 | 0.2054 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0424 (6) | 0.0385 (6) | 0.0397 (6) | 0.0314 (5) | 0.0270 (5) | 0.0220 (5) |
O1 | 0.076 (3) | 0.073 (3) | 0.122 (5) | 0.063 (3) | 0.070 (4) | 0.075 (3) |
O2 | 0.042 (2) | 0.059 (3) | 0.048 (2) | 0.0303 (19) | 0.0312 (18) | 0.0238 (19) |
O3 | 0.048 (3) | 0.088 (3) | 0.100 (4) | 0.047 (3) | 0.041 (3) | 0.068 (3) |
O4 | 0.090 (4) | 0.071 (3) | 0.057 (3) | 0.056 (3) | 0.042 (3) | 0.009 (2) |
S2 | 0.0461 (8) | 0.0567 (8) | 0.0614 (9) | 0.0393 (7) | 0.0330 (7) | 0.0384 (7) |
O5 | 0.154 (7) | 0.065 (4) | 0.075 (4) | 0.034 (4) | 0.072 (4) | 0.029 (3) |
O6 | 0.086 (4) | 0.065 (3) | 0.106 (4) | 0.058 (3) | 0.072 (3) | 0.056 (3) |
O7 | 0.146 (7) | 0.079 (4) | 0.072 (4) | 0.081 (5) | 0.033 (4) | 0.014 (3) |
O8 | 0.075 (7) | 0.216 (14) | 0.28 (2) | 0.109 (9) | 0.116 (11) | 0.217 (17) |
O8' | 0.084 (12) | 0.049 (9) | 0.049 (10) | 0.047 (8) | 0.047 (8) | 0.022 (7) |
O1A | 0.070 (3) | 0.054 (2) | 0.0387 (18) | 0.051 (2) | 0.0190 (18) | 0.0196 (17) |
O1B | 0.121 (4) | 0.093 (4) | 0.051 (2) | 0.096 (4) | 0.052 (3) | 0.042 (2) |
C11 | 0.036 (3) | 0.041 (3) | 0.037 (3) | 0.027 (2) | 0.009 (2) | 0.014 (2) |
C12 | 0.041 (3) | 0.031 (2) | 0.036 (2) | 0.027 (2) | 0.018 (2) | 0.016 (2) |
N11 | 0.048 (3) | 0.038 (2) | 0.045 (2) | 0.031 (2) | 0.027 (2) | 0.0205 (18) |
C13 | 0.063 (4) | 0.046 (3) | 0.039 (3) | 0.044 (3) | 0.011 (3) | 0.011 (2) |
C14 | 0.036 (3) | 0.033 (2) | 0.052 (3) | 0.024 (2) | 0.014 (2) | 0.018 (2) |
N12 | 0.042 (3) | 0.042 (2) | 0.054 (3) | 0.030 (2) | 0.024 (2) | 0.027 (2) |
C15 | 0.059 (4) | 0.040 (3) | 0.082 (5) | 0.040 (3) | 0.033 (4) | 0.030 (3) |
N13 | 0.074 (4) | 0.064 (4) | 0.123 (6) | 0.058 (4) | 0.059 (4) | 0.049 (4) |
C16 | 0.047 (4) | 0.047 (3) | 0.110 (6) | 0.029 (3) | 0.040 (4) | 0.041 (4) |
O2A | 0.048 (2) | 0.063 (3) | 0.052 (2) | 0.042 (2) | 0.0201 (19) | 0.015 (2) |
O2B | 0.056 (3) | 0.063 (3) | 0.058 (3) | 0.041 (2) | 0.013 (2) | −0.010 (2) |
C21 | 0.048 (3) | 0.038 (3) | 0.040 (3) | 0.035 (3) | 0.025 (2) | 0.017 (2) |
C22 | 0.037 (2) | 0.041 (3) | 0.034 (2) | 0.028 (2) | 0.019 (2) | 0.017 (2) |
N21 | 0.047 (2) | 0.045 (2) | 0.0267 (19) | 0.035 (2) | 0.0177 (18) | 0.0152 (17) |
C23 | 0.049 (3) | 0.058 (3) | 0.030 (2) | 0.042 (3) | 0.019 (2) | 0.019 (2) |
C24 | 0.039 (3) | 0.046 (3) | 0.034 (3) | 0.032 (2) | 0.018 (2) | 0.019 (2) |
N22 | 0.046 (3) | 0.048 (3) | 0.067 (3) | 0.034 (2) | 0.032 (3) | 0.033 (3) |
C25 | 0.061 (4) | 0.055 (4) | 0.075 (5) | 0.042 (3) | 0.039 (4) | 0.038 (3) |
N23 | 0.048 (3) | 0.065 (3) | 0.074 (4) | 0.045 (3) | 0.040 (3) | 0.034 (3) |
C26 | 0.039 (3) | 0.051 (3) | 0.061 (4) | 0.030 (3) | 0.025 (3) | 0.022 (3) |
OW1 | 0.082 (4) | 0.058 (3) | 0.047 (3) | 0.056 (3) | 0.031 (2) | 0.024 (2) |
OW2 | 0.116 (5) | 0.127 (6) | 0.039 (3) | 0.104 (5) | 0.033 (3) | 0.018 (3) |
OW3 | 0.076 (4) | 0.102 (5) | 0.100 (4) | 0.048 (4) | 0.039 (4) | 0.068 (4) |
S1—O1 | 1.451 (4) | N13—H13 | 0.8600 |
S1—O4 | 1.452 (5) | C16—H16 | 0.9300 |
S1—O2 | 1.458 (4) | O2A—C21 | 1.217 (7) |
S1—O3 | 1.469 (5) | O2B—C21 | 1.303 (7) |
S2—O8 | 1.436 (9) | O2B—H2B | 0.8200 |
S2—O5 | 1.443 (7) | C21—C22 | 1.517 (7) |
S2—O7 | 1.459 (7) | C22—N21 | 1.477 (7) |
S2—O6 | 1.471 (5) | C22—C23 | 1.530 (8) |
S2—O8' | 1.581 (15) | C22—H22 | 0.9800 |
O8'—O8 | 1.20 (2) | N21—H21A | 0.8900 |
O1A—C11 | 1.218 (7) | N21—H21B | 0.8900 |
O1B—C11 | 1.286 (8) | N21—H21C | 0.8900 |
O1B—H1B | 0.8200 | C23—C24 | 1.484 (8) |
C11—C12 | 1.505 (8) | C23—H23A | 0.9700 |
C12—N11 | 1.497 (7) | C23—H23B | 0.9700 |
C12—C13 | 1.527 (8) | C24—C26 | 1.364 (9) |
C12—H12 | 0.9800 | C24—N22 | 1.376 (8) |
N11—H11A | 0.8900 | N22—C25 | 1.302 (10) |
N11—H11B | 0.8900 | N22—H22A | 0.8600 |
N11—H11C | 0.8900 | C25—N23 | 1.314 (10) |
C13—C14 | 1.487 (8) | C25—H25 | 0.9300 |
C13—H13A | 0.9700 | N23—C26 | 1.370 (9) |
C13—H13B | 0.9700 | N23—H23 | 0.8600 |
C14—C16 | 1.336 (10) | C26—H26 | 0.9300 |
C14—N12 | 1.382 (8) | OW1—HW1 | 0.88 (9) |
N12—C15 | 1.322 (9) | OW1—HW2 | 0.68 (8) |
N12—H12A | 0.8600 | OW2—HW3 | 0.65 (8) |
C15—N13 | 1.274 (10) | OW2—HW4 | 0.82 (12) |
C15—H15 | 0.9300 | OW3—HW5 | 0.976 (6) |
N13—C16 | 1.366 (10) | OW3—HW6 | 0.975 (7) |
O1—S1—O4 | 111.5 (4) | N12—C15—H15 | 125.8 |
O1—S1—O2 | 109.4 (3) | C15—N13—C16 | 110.9 (6) |
O4—S1—O2 | 107.5 (3) | C15—N13—H13 | 124.5 |
O1—S1—O3 | 108.2 (3) | C16—N13—H13 | 124.5 |
O4—S1—O3 | 109.3 (4) | C14—C16—N13 | 105.9 (6) |
O2—S1—O3 | 110.9 (3) | C14—C16—H16 | 127.0 |
O8—S2—O5 | 105.1 (8) | N13—C16—H16 | 127.0 |
O8—S2—O7 | 116.0 (10) | C21—O2B—H2B | 109.5 |
O5—S2—O7 | 102.1 (5) | O2A—C21—O2B | 124.4 (5) |
O8—S2—O6 | 112.6 (5) | O2A—C21—C22 | 123.1 (5) |
O5—S2—O6 | 109.2 (4) | O2B—C21—C22 | 112.4 (5) |
O7—S2—O6 | 111.0 (4) | N21—C22—C21 | 107.6 (4) |
O8—S2—O8' | 46.4 (9) | N21—C22—C23 | 111.6 (4) |
O5—S2—O8' | 145.9 (8) | C21—C22—C23 | 111.0 (4) |
O7—S2—O8' | 81.4 (7) | N21—C22—H22 | 108.9 |
O6—S2—O8' | 100.7 (7) | C21—C22—H22 | 108.9 |
O8—O8'—S2 | 60.4 (8) | C23—C22—H22 | 108.9 |
O8'—O8—S2 | 73.2 (10) | C22—N21—H21A | 109.5 |
C11—O1B—H1B | 109.5 | C22—N21—H21B | 109.5 |
O1A—C11—O1B | 125.2 (5) | H21A—N21—H21B | 109.5 |
O1A—C11—C12 | 121.6 (5) | C22—N21—H21C | 109.5 |
O1B—C11—C12 | 113.2 (5) | H21A—N21—H21C | 109.5 |
N11—C12—C11 | 109.3 (4) | H21B—N21—H21C | 109.5 |
N11—C12—C13 | 111.7 (5) | C24—C23—C22 | 114.9 (4) |
C11—C12—C13 | 111.4 (4) | C24—C23—H23A | 108.5 |
N11—C12—H12 | 108.1 | C22—C23—H23A | 108.5 |
C11—C12—H12 | 108.1 | C24—C23—H23B | 108.5 |
C13—C12—H12 | 108.1 | C22—C23—H23B | 108.5 |
C12—N11—H11A | 109.5 | H23A—C23—H23B | 107.5 |
C12—N11—H11B | 109.5 | C26—C24—N22 | 105.0 (5) |
H11A—N11—H11B | 109.5 | C26—C24—C23 | 132.4 (6) |
C12—N11—H11C | 109.5 | N22—C24—C23 | 122.6 (5) |
H11A—N11—H11C | 109.5 | C25—N22—C24 | 110.1 (5) |
H11B—N11—H11C | 109.5 | C25—N22—H22A | 124.9 |
C14—C13—C12 | 115.6 (5) | C24—N22—H22A | 124.9 |
C14—C13—H13A | 108.4 | N22—C25—N23 | 109.0 (6) |
C12—C13—H13A | 108.4 | N22—C25—H25 | 125.5 |
C14—C13—H13B | 108.4 | N23—C25—H25 | 125.5 |
C12—C13—H13B | 108.4 | C25—N23—C26 | 108.5 (6) |
H13A—C13—H13B | 107.4 | C25—N23—H23 | 125.8 |
C16—C14—N12 | 106.6 (6) | C26—N23—H23 | 125.8 |
C16—C14—C13 | 130.5 (6) | C24—C26—N23 | 107.4 (6) |
N12—C14—C13 | 122.9 (6) | C24—C26—H26 | 126.3 |
C15—N12—C14 | 108.1 (5) | N23—C26—H26 | 126.3 |
C15—N12—H12A | 125.9 | HW1—OW1—HW2 | 114 (8) |
C14—N12—H12A | 125.9 | HW3—OW2—HW4 | 102 (9) |
N13—C15—N12 | 108.4 (5) | HW5—OW3—HW6 | 108.4 (6) |
N13—C15—H15 | 125.8 | ||
O5—S2—O8'—O8 | 40.2 (17) | N12—C14—C16—N13 | 1.8 (10) |
O7—S2—O8'—O8 | 139.1 (11) | C13—C14—C16—N13 | 179.6 (7) |
O6—S2—O8'—O8 | −111.0 (11) | C15—N13—C16—C14 | −0.6 (11) |
O5—S2—O8—O8' | −158.0 (10) | O2A—C21—C22—N21 | 0.4 (8) |
O7—S2—O8—O8' | −46.1 (11) | O2B—C21—C22—N21 | −174.9 (5) |
O6—S2—O8—O8' | 83.3 (13) | O2A—C21—C22—C23 | 122.8 (6) |
O1A—C11—C12—N11 | 11.9 (8) | O2B—C21—C22—C23 | −52.5 (7) |
O1B—C11—C12—N11 | −168.5 (5) | N21—C22—C23—C24 | −53.8 (7) |
O1A—C11—C12—C13 | 135.9 (6) | C21—C22—C23—C24 | −173.8 (5) |
O1B—C11—C12—C13 | −44.6 (7) | C22—C23—C24—C26 | −82.1 (8) |
N11—C12—C13—C14 | −61.9 (7) | C22—C23—C24—N22 | 97.2 (7) |
C11—C12—C13—C14 | 175.6 (6) | C26—C24—N22—C25 | −0.1 (8) |
C12—C13—C14—C16 | 118.4 (9) | C23—C24—N22—C25 | −179.5 (6) |
C12—C13—C14—N12 | −64.2 (9) | C24—N22—C25—N23 | −0.3 (9) |
C16—C14—N12—C15 | −2.5 (9) | N22—C25—N23—C26 | 0.6 (9) |
C13—C14—N12—C15 | 179.5 (6) | N22—C24—C26—N23 | 0.5 (7) |
C14—N12—C15—N13 | 2.1 (9) | C23—C24—C26—N23 | 179.8 (6) |
N12—C15—N13—C16 | −1.0 (11) | C25—N23—C26—C24 | −0.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···OW1 | 0.82 | 1.68 | 2.474 (6) | 162 |
N11—H11A···O7i | 0.89 | 1.92 | 2.795 (8) | 169 |
N11—H11B···O2ii | 0.89 | 2.23 | 3.046 (6) | 153 |
N11—H11B···O4ii | 0.89 | 2.32 | 3.055 (8) | 140 |
N11—H11C···O2Aiii | 0.89 | 2.12 | 2.989 (6) | 164 |
N12—H12A···O3i | 0.86 | 1.82 | 2.662 (7) | 166 |
N13—H13···O1iv | 0.86 | 1.98 | 2.794 (8) | 156 |
O2B—H2B···OW2iv | 0.82 | 1.67 | 2.485 (7) | 172 |
N21—H21A···O4v | 0.89 | 1.86 | 2.714 (6) | 161 |
N21—H21B···O6v | 0.89 | 1.89 | 2.767 (7) | 170 |
N21—H21C···O1Av | 0.89 | 2.09 | 2.895 (6) | 149 |
N22—H22A···O8v | 0.86 | 1.81 | 2.665 (11) | 175 |
N22—H22A···O8′v | 0.86 | 1.95 | 2.713 (19) | 148 |
N23—H23···O6vi | 0.86 | 2.05 | 2.821 (7) | 150 |
OW1—HW1···O5vi | 0.88 (9) | 1.87 (9) | 2.629 (9) | 144 (7) |
OW1—HW2···O3 | 0.68 (8) | 2.08 (8) | 2.684 (8) | 148 (8) |
OW2—HW3···O2 | 0.65 (8) | 2.09 (8) | 2.666 (7) | 149 (8) |
OW2—HW4···O8vi | 0.82 (12) | 1.79 (12) | 2.588 (14) | 162 (10) |
OW3—HW5···O1ii | 0.98 | 1.80 | 2.775 (13) | 180 |
OW3—HW6···O7 | 0.98 | 1.93 | 2.909 (15) | 179 |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y, z−1; (iv) x+1, y−1, z; (v) x+1, y, z+1; (vi) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | 2C6H11N3O22+·2SO42−·3H2O |
Mr | 280.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.3400 (13), 8.9291 (11), 10.724 (2) |
α, β, γ (°) | 102.576 (13), 107.704 (15), 119.667 (11) |
V (Å3) | 592.03 (16) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.81 |
Crystal size (mm) | 0.5 × 0.3 × 0.15 |
Data collection | |
Diffractometer | Enraf-Nonius sealed-tube diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.418, 0.656 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2303, 2303, 2280 |
Rint | ? |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.148, 1.05 |
No. of reflections | 2303 |
No. of parameters | 346 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.79, −0.48 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.03 (3) |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1999), SHELXL97.
O1A—C11 | 1.218 (7) | O2A—C21 | 1.217 (7) |
O1B—C11 | 1.286 (8) | O2B—C21 | 1.303 (7) |
O1A—C11—C12—N11 | 11.9 (8) | O2A—C21—C22—N21 | 0.4 (8) |
N11—C12—C13—C14 | −61.9 (7) | N21—C22—C23—C24 | −53.8 (7) |
C11—C12—C13—C14 | 175.6 (6) | C21—C22—C23—C24 | −173.8 (5) |
C12—C13—C14—C16 | 118.4 (9) | C22—C23—C24—C26 | −82.1 (8) |
C12—C13—C14—N12 | −64.2 (9) | C22—C23—C24—N22 | 97.2 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···OW1 | 0.82 | 1.68 | 2.474 (6) | 162 |
N11—H11A···O7i | 0.89 | 1.92 | 2.795 (8) | 169 |
N11—H11B···O2ii | 0.89 | 2.23 | 3.046 (6) | 153 |
N11—H11B···O4ii | 0.89 | 2.32 | 3.055 (8) | 140 |
N11—H11C···O2Aiii | 0.89 | 2.12 | 2.989 (6) | 164 |
N12—H12A···O3i | 0.86 | 1.82 | 2.662 (7) | 166 |
N13—H13···O1iv | 0.86 | 1.98 | 2.794 (8) | 156 |
O2B—H2B···OW2iv | 0.82 | 1.67 | 2.485 (7) | 172 |
N21—H21A···O4v | 0.89 | 1.86 | 2.714 (6) | 161 |
N21—H21B···O6v | 0.89 | 1.89 | 2.767 (7) | 170 |
N21—H21C···O1Av | 0.89 | 2.09 | 2.895 (6) | 149 |
N22—H22A···O8v | 0.86 | 1.81 | 2.665 (11) | 175 |
N22—H22A···O8'v | 0.86 | 1.95 | 2.713 (19) | 148 |
N23—H23···O6vi | 0.86 | 2.05 | 2.821 (7) | 150 |
OW1—HW1···O5vi | 0.88 (9) | 1.87 (9) | 2.629 (9) | 144 (7) |
OW1—HW2···O3 | 0.68 (8) | 2.08 (8) | 2.684 (8) | 148 (8) |
OW2—HW3···O2 | 0.65 (8) | 2.09 (8) | 2.666 (7) | 149 (8) |
OW2—HW4···O8vi | 0.82 (12) | 1.79 (12) | 2.588 (14) | 162 (10) |
OW3—HW5···O1ii | 0.98 | 1.80 | 2.775 (13) | 180 |
OW3—HW6···O7 | 0.98 | 1.93 | 2.909 (15) | 179 |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z; (iii) x−1, y, z−1; (iv) x+1, y−1, z; (v) x+1, y, z+1; (vi) x, y, z+1. |
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The crystal structures of L-histidine (Madden et al., 1972), L-histidine hydrochloride monohydrate (Fuess et al., 1977), DL-histidine hydrochloride dihydrate (Bennett et al., 1970), L-histidinium dinitrate (Asath Bahadur, 1992), DL-histidinium dinitrate (Asath Bahadur, 1992), DL-histidinium sulfamate (Asath Bahadur, 1992) and DL-histidine perchlorate (Asath Bahadur, 1992) have been reported earlier. In the present study, the crystal structure determination of bis(L-histidinium sulfate) trihydrate, (I), was undertaken.
The two crystallographically independent diprotonated histidinium molecules (A and B) have similar geometries. The histidinium molecule consists of two groups of nearly coplanar atoms. The chain has a straight conformation in molecules A and B which adopts the open form, as is present in L-histidine (Madden et al., 1972) and DL-histidine hydrochloride (Bennett et al., 1970). The conformation angles are such that χ1 is in the gauche II conformation [-61.9 (7) and -53.8 (7)°] for both molecules having a closed conformation (Pratap et al., 2000) (Table 1).
The sulfate anion links the amino N atom and the imidazolinium group of both molecules A and B and the water molecules through hydrogen bonds and stabilizes the structure (Table 2). The sulfate anion links the imidazolinium rings of both molecules, extending as a chain along the a axis (N12—H12A···O3i, N13—H13···O1iv, N22—H22A···O8'v and N22—H23···O6vii). A three-centered (bifurcated) hydrogen bond is observed in the case of the amino N atom of molecule A with sulfate O atoms (Jeffrey & Saenger, 1991). The water molecules OW1 and OW2, as acceptors, link the carboxyl O atom of both molecules through strong hydrogen bonds. Both crystallographically independent sulfate anions are linked to the three water molecules by hydrogen bonds. Molecules A and B are engaged in a straight (S1) head-to-tail sequence since the hydrogen bonds, viz. N11—H11C···O2Aiii and N21—H21C···O1Av, connect the amino acids along the 101 plane (Vijayan, 1988), as a closed dimer (Jeffrey & Saenger, 1991).