Supporting information
Crystallographic Information File (CIF) | |
Structure factor file (CIF format) |
CCDC reference: 132056
Data collection: CAD4; cell refinement: CAD4; data reduction: CAD4; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEP.
C6H16N2O22+·HI2O6−·IO3− | F(000) = 628 |
Mr = 673.92 | Dx = 2.87 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.360 (2) Å | Cell parameters from 24 reflections |
b = 6.330 (1) Å | θ = 14–16° |
c = 14.750 (3) Å | µ = 6.07 mm−1 |
β = 92.86 (3)° | T = 293 K |
V = 779.6 (3) Å3 | Plate, colourless |
Z = 2 | 0.6 × 0.2 × 0.1 mm |
Enraf-Nonius CAD4 diffractometer | 2443 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.117 |
Graphite monochromator | θmax = 30.0°, θmin = 2.4° |
ω–2θ scans | h = 0→11 |
Absorption correction: empirical (using intensity measurements) via ψ scans ? | k = 0→8 |
Tmin = ?, Tmax = ? | l = −20→20 |
2601 measured reflections | 3 standard reflections every 3600 min |
2452 independent reflections | intensity decay: 10% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.034 | Calculated w = 1/[σ2(Fo2) + (0.0765P)2 + 1.2606P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max = 0.210 |
S = 1.07 | Δρmax = 3.06 e Å−3 |
2452 reflections | Δρmin = −1.96 e Å−3 |
200 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0100 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.02 (5) |
C6H16N2O22+·HI2O6−·IO3− | V = 779.6 (3) Å3 |
Mr = 673.92 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.360 (2) Å | µ = 6.07 mm−1 |
b = 6.330 (1) Å | T = 293 K |
c = 14.750 (3) Å | 0.6 × 0.2 × 0.1 mm |
β = 92.86 (3)° |
Enraf-Nonius CAD4 diffractometer | 2443 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) via ψ scans ? | Rint = 0.117 |
Tmin = ?, Tmax = ? | 3 standard reflections every 3600 min |
2601 measured reflections | intensity decay: 10% |
2452 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters not refined |
wR(F2) = 0.092 | (Δ/σ)max = 0.210 |
S = 1.07 | Δρmax = 3.06 e Å−3 |
2452 reflections | Δρmin = −1.96 e Å−3 |
200 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
1 restraint | Absolute structure parameter: 0.02 (5) |
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 on F2 for the reflections with F2 > σ(F2) or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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 | ||
I1 | 0.72398 (4) | 0.38284 (7) | 0.87423 (3) | 0.01554 (13) | |
O11 | 0.6527 (8) | 0.1946 (11) | 0.7880 (4) | 0.0259 (12) | |
O12 | 0.6660 (8) | 0.6270 (11) | 0.8169 (4) | 0.0262 (12) | |
O13 | 0.9336 (5) | 0.3776 (14) | 0.8507 (4) | 0.0279 (13) | |
I2 | 0.22512 (4) | 0.35791 (7) | 0.93412 (3) | 0.01528 (13) | |
O21 | 0.1524 (7) | 0.1153 (11) | 0.9821 (5) | 0.0277 (12) | |
O22 | 0.1510 (7) | 0.5336 (13) | 1.0289 (4) | 0.0272 (14) | |
H22A | 0.0547 (7) | 0.5546 (13) | 1.0204 (4) | 0.041* | |
O23 | 0.4277 (6) | 0.3537 (11) | 0.9774 (4) | 0.0238 (11) | |
I3 | 0.43204 (5) | −0.08631 (7) | 0.81957 (2) | 0.01402 (13) | |
O31 | 0.2990 (7) | 0.1453 (10) | 0.8057 (4) | 0.0230 (11) | |
O32 | 0.4450 (7) | −0.1352 (12) | 0.7001 (3) | 0.0224 (11) | |
O33 | 0.2810 (7) | −0.2824 (10) | 0.8399 (4) | 0.0248 (12) | |
O1 | 0.5864 (7) | 0.4468 (14) | 0.5196 (4) | 0.032 (2) | |
O2 | 0.3679 (7) | 0.4472 (15) | 0.4265 (4) | 0.033 (2) | |
H2B | 0.4316 (7) | 0.4177 (15) | 0.3852 (4) | 0.080* | |
C1 | 0.4459 (9) | 0.4389 (14) | 0.5065 (4) | 0.0206 (13) | |
C2 | 0.3304 (8) | 0.4029 (15) | 0.5828 (4) | 0.0212 (13) | |
H2A | 0.2865 (8) | 0.2632 (15) | 0.5770 (4) | 0.080* | |
C3 | 0.1906 (9) | 0.5578 (15) | 0.5788 (5) | 0.0225 (14) | |
H3A | 0.1388 (9) | 0.5574 (15) | 0.5192 (5) | 0.080* | |
H3B | 0.2342 (9) | 0.6963 (15) | 0.5896 (5) | 0.080* | |
C4 | 0.0650 (10) | 0.5108 (17) | 0.6487 (6) | 0.028 (2) | |
H4A | 0.0245 (10) | 0.3701 (17) | 0.6398 (6) | 0.080* | |
H4B | 0.1153 (10) | 0.5182 (17) | 0.7086 (6) | 0.080* | |
C5 | −0.0709 (10) | 0.6730 (17) | 0.6432 (6) | 0.030 (2) | |
H5A | −0.1017 (10) | 0.6940 (17) | 0.5803 (6) | 0.080* | |
H5B | −0.1608 (10) | 0.6127 (17) | 0.6719 (6) | 0.080* | |
C6 | −0.0343 (9) | 0.8843 (19) | 0.6861 (5) | 0.029 (2) | |
H6A | 0.0694 (9) | 0.9299 (19) | 0.6688 (5) | 0.080* | |
H6B | −0.1116 (9) | 0.9867 (19) | 0.6641 (5) | 0.080* | |
N7 | −0.0361 (8) | 0.8759 (15) | 0.7870 (4) | 0.0260 (14) | |
H7A | −0.0149 (8) | 1.0036 (15) | 0.8098 (4) | 0.039* | |
H7B | 0.0379 (8) | 0.7849 (15) | 0.8082 (4) | 0.039* | |
H7C | −0.1322 (8) | 0.8340 (15) | 0.8032 (4) | 0.039* | |
N8 | 0.4238 (8) | 0.4192 (13) | 0.6700 (4) | 0.0222 (12) | |
H8A | 0.5048 (8) | 0.3280 (13) | 0.6706 (4) | 0.033* | |
H8B | 0.3610 (8) | 0.3897 (13) | 0.7153 (4) | 0.033* | |
H8C | 0.4619 (8) | 0.5499 (13) | 0.6767 (4) | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0147 (2) | 0.0116 (2) | 0.0204 (2) | 0.00019 (14) | 0.00143 (12) | 0.0000 (2) |
O11 | 0.031 (3) | 0.022 (3) | 0.024 (3) | −0.006 (2) | 0.000 (2) | −0.004 (2) |
O12 | 0.030 (3) | 0.019 (3) | 0.030 (3) | 0.005 (2) | 0.004 (2) | 0.007 (2) |
O13 | 0.015 (2) | 0.043 (4) | 0.026 (2) | −0.003 (3) | 0.005 (2) | 0.005 (3) |
I2 | 0.0142 (2) | 0.0118 (2) | 0.0201 (2) | −0.00007 (14) | 0.00309 (13) | 0.00182 (15) |
O21 | 0.026 (3) | 0.020 (3) | 0.037 (3) | −0.005 (2) | 0.003 (2) | 0.011 (3) |
O22 | 0.026 (3) | 0.032 (4) | 0.024 (3) | 0.003 (2) | 0.005 (2) | −0.013 (2) |
O23 | 0.016 (2) | 0.022 (3) | 0.034 (3) | 0.000 (2) | 0.002 (2) | 0.005 (3) |
I3 | 0.0192 (2) | 0.0082 (2) | 0.0149 (2) | −0.00035 (14) | 0.00294 (12) | −0.00005 (14) |
O31 | 0.026 (3) | 0.018 (3) | 0.025 (3) | 0.007 (2) | 0.006 (2) | 0.001 (2) |
O32 | 0.035 (3) | 0.018 (3) | 0.014 (2) | −0.006 (2) | 0.005 (2) | −0.002 (2) |
O33 | 0.025 (3) | 0.012 (3) | 0.039 (3) | −0.006 (2) | 0.007 (2) | 0.007 (2) |
O1 | 0.027 (3) | 0.043 (4) | 0.027 (3) | −0.004 (3) | 0.007 (2) | 0.003 (3) |
O2 | 0.033 (3) | 0.049 (5) | 0.019 (2) | 0.006 (3) | 0.004 (2) | −0.001 (3) |
C1 | 0.029 (3) | 0.017 (3) | 0.016 (3) | 0.002 (3) | 0.004 (2) | −0.001 (3) |
C2 | 0.023 (3) | 0.020 (4) | 0.021 (3) | −0.001 (3) | 0.005 (2) | −0.005 (3) |
C3 | 0.026 (3) | 0.021 (4) | 0.021 (3) | 0.001 (3) | 0.008 (2) | 0.002 (3) |
C4 | 0.026 (3) | 0.025 (4) | 0.035 (4) | 0.006 (3) | 0.008 (3) | 0.003 (4) |
C5 | 0.022 (3) | 0.031 (5) | 0.038 (4) | 0.000 (3) | 0.005 (3) | −0.007 (4) |
C6 | 0.028 (3) | 0.033 (5) | 0.028 (3) | 0.005 (4) | 0.005 (2) | 0.004 (4) |
N7 | 0.029 (3) | 0.025 (4) | 0.025 (3) | 0.001 (3) | 0.003 (2) | −0.006 (3) |
N8 | 0.025 (3) | 0.018 (3) | 0.023 (3) | 0.003 (3) | 0.004 (2) | 0.002 (3) |
I1—O11 | 1.821 (6) | I1—O21i | 2.740 (7) |
I1—O12 | 1.816 (7) | I1—O22ii | 2.805 (7) |
I1—O13 | 1.804 (5) | I1—O23 | 2.977 (5) |
I2—O21 | 1.809 (7) | I2—O13iii | 2.677 (5) |
I2—O22 | 1.914 (6) | I2—O31 | 2.429 (6) |
I2—O23 | 1.780 (5) | I2—O33iv | 2.720 (6) |
I3—O31 | 1.845 (6) | I3—O11 | 2.620 (7) |
I3—O32 | 1.798 (5) | I3—O12v | 2.670 (7) |
I3—O33 | 1.806 (6) | I3—O23ii | 3.184 (6) |
O1—C1 | 1.182 (9) | C1—O2 | 1.320 (9) |
C2—C1 | 1.537 (10) | C2—C3 | 1.524 (11) |
C2—N8 | 1.474 (9) | C3—C4 | 1.538 (11) |
C5—C4 | 1.531 (13) | C5—C6 | 1.50 (2) |
N7—C6 | 1.491 (10) | ||
O22···O21vi | 2.586 (8) | O2···O32vii | 2.549 (8) |
N8···O11 | 2.895 (10) | N7···O33iv | 2.903 (10) |
N8···O31 | 2.883 (9) | N7···O12iii | 2.998 (10) |
N8···O32iv | 2.859 (11) | ||
O12—I1—O11 | 99.3 (3) | C3—C2—C1 | 112.6 (7) |
O13—I1—O11 | 98.1 (3) | N7—C6—C5 | 112.1 (9) |
O13—I1—O12 | 99.5 (3) | O23—I2—O21 | 100.3 (3) |
O23—I2—O31 | 89.8 (2) | O23—I2—O22 | 94.8 (3) |
O21—I2—O31 | 86.5 (3) | O21—I2—O22 | 94.6 (4) |
O22—I2—O31 | 175.0 (2) | O1—C1—O2 | 126.0 (7) |
O32—I3—O33 | 97.0 (3) | O1—C1—C2 | 122.8 (7) |
O32—I3—O31 | 95.4 (3) | O2—C1—C2 | 111.1 (6) |
O33—I3—O31 | 98.1 (3) | C4—C3—C2 | 113.4 (7) |
I3—O31—I2 | 121.9 (3) | C5—C4—C3 | 111.4 (8) |
N8—C2—C3 | 111.2 (6) | C6—C5—C4 | 116.0 (7) |
N8—C2—C1 | 107.7 (6) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+2; (iii) x−1, y, z; (iv) x, y+1, z; (v) x, y−1, z; (vi) −x, y+1/2, −z+2; (vii) −x+1, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C6H16N2O22+·HI2O6−·IO3− |
Mr | 673.92 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 8.360 (2), 6.330 (1), 14.750 (3) |
β (°) | 92.86 (3) |
V (Å3) | 779.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 6.07 |
Crystal size (mm) | 0.6 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Enraf-Nonius CAD4 diffractometer |
Absorption correction | Empirical (using intensity measurements) via ψ scans |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2601, 2452, 2443 |
Rint | 0.117 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.092, 1.07 |
No. of reflections | 2452 |
No. of parameters | 200 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters not refined |
(Δ/σ)max | 0.210 |
Δρmax, Δρmin (e Å−3) | 3.06, −1.96 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | 0.02 (5) |
Computer programs: CAD4, SHELXS86 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), ORTEP.
I1—O11 | 1.821 (6) | I1—O21i | 2.740 (7) |
I1—O12 | 1.816 (7) | I1—O22ii | 2.805 (7) |
I1—O13 | 1.804 (5) | I1—O23 | 2.977 (5) |
I2—O21 | 1.809 (7) | I2—O13iii | 2.677 (5) |
I2—O22 | 1.914 (6) | I2—O31 | 2.429 (6) |
I2—O23 | 1.780 (5) | I2—O33iv | 2.720 (6) |
I3—O31 | 1.845 (6) | I3—O11 | 2.620 (7) |
I3—O32 | 1.798 (5) | I3—O12v | 2.670 (7) |
I3—O33 | 1.806 (6) | I3—O23ii | 3.184 (6) |
O1—C1 | 1.182 (9) | C1—O2 | 1.320 (9) |
C2—C1 | 1.537 (10) | C2—C3 | 1.524 (11) |
C2—N8 | 1.474 (9) | C3—C4 | 1.538 (11) |
C5—C4 | 1.531 (13) | C5—C6 | 1.50 (2) |
N7—C6 | 1.491 (10) | ||
O22···O21vi | 2.586 (8) | O2···O32vii | 2.549 (8) |
N8···O11 | 2.895 (10) | N7···O33iv | 2.903 (10) |
N8···O31 | 2.883 (9) | N7···O12iii | 2.998 (10) |
N8···O32iv | 2.859 (11) | ||
O12—I1—O11 | 99.3 (3) | O23—I2—O21 | 100.3 (3) |
O13—I1—O11 | 98.1 (3) | O23—I2—O22 | 94.8 (3) |
O13—I1—O12 | 99.5 (3) | O21—I2—O22 | 94.6 (4) |
O32—I3—O33 | 97.0 (3) | O1—C1—O2 | 126.0 (7) |
O32—I3—O31 | 95.4 (3) | O1—C1—C2 | 122.8 (7) |
O33—I3—O31 | 98.1 (3) | O2—C1—C2 | 111.1 (6) |
N8—C2—C3 | 111.2 (6) | C4—C3—C2 | 113.4 (7) |
N8—C2—C1 | 107.7 (6) | C5—C4—C3 | 111.4 (8) |
C3—C2—C1 | 112.6 (7) | C6—C5—C4 | 116.0 (7) |
N7—C6—C5 | 112.1 (9) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+2; (iii) x−1, y, z; (iv) x, y+1, z; (v) x, y−1, z; (vi) −x, y+1/2, −z+2; (vii) −x+1, y+1/2, −z+1. |