The crystal structures of the energetic materials biguanidinium mono-dinitramide C
2H
8N
.N
3O
, (BIGH)(DN), and biguanidinium bis-dinitramide C
2H
9N
.2N
3O
, (BIGH
2)(DN)
2, have been determined at several temperatures in the range 85-298 K using single-crystal X-ray diffraction techniques. The thermal expansion second-rank tensors have been determined to describe the thermal behavior of the crystals studied. Strongly anisotropic thermal expansion is most important in the direction perpendicular to the least-squares planes of the dinitramide ions in both cases, suggesting that the atomic thermal motion is significantly anharmonic in these crystals. Anharmonicity of thermal motion is also evident from the non-linear temperature dependence of the atomic displacement parameters. Rigid-body analysis of thermal motion both of dinitramide anions and of biguanidinium cations was performed using the libration and translation second-rank tensors. For both compounds, the libration thermal motion is strongly anisotropic with the dominating libration axes oriented in a similar manner in both anions and cations. Although the translation motion of the ions is not strongly anisotropic, the axes of largest thermal displacements are close to the directions of greatest thermal expansion of the crystals.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889803016182/do0021sup1.cif
Contains datablocks I100K, I150K, I200K, I250K, I298K, II85K, II100K, II150K, II200K, II250K, II298K, global |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021I100Ksup2.fcf
Contains datablock I100K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021I150Ksup3.fcf
Contains datablock I150K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021I200Ksup4.fcf
Contains datablock I200K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021I250Ksup5.fcf
Contains datablock I250K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021I298Ksup6.fcf
Contains datablock I298K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II85Ksup7.fcf
Contains datablock II85K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II100Ksup8.fcf
Contains datablock II100K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II150Ksup9.fcf
Contains datablock II150K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II200Ksup10.fcf
Contains datablock II200K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II250Ksup11.fcf
Contains datablock II250K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0021889803016182/do0021II298Ksup12.fcf
Contains datablock II298K |
CCDC references: 233144; 233145; 233146; 233147; 233148; 233149; 233150; 233151; 233152; 233153; 233154
For all compounds, data collection: Siemens SMART, 1996a; cell refinement: Siemens SAINT, 1996b; data reduction: Siemens SAINT, 1996b; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and the Toledo cifomatic.
Crystal data top
| C2H8N8O4 | Z = 2 |
| Mr = 208.16 | F(000) = 216 |
| Triclinic, P1 | Dx = 1.681 Mg m−3 |
| a = 4.2928 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3043 (2) Å | Cell parameters from 2330 reflections |
| c = 10.5438 (3) Å | θ = 5.8–22.2° |
| α = 85.236 (2)° | µ = 0.15 mm−1 |
| β = 82.032 (2)° | T = 100 K |
| γ = 81.190 (2)° | Block, colourless |
| V = 411.33 (2) Å3 | 0.23 × 0.15 × 0.06 mm |
Data collection top
Platform
diffractometer | 2046 independent reflections |
| Radiation source: fine-focus sealed tube | 1425 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.053 |
| ω scans | θmax = 28.3°, θmin = 2.0° |
| Absorption correction: empirical :Multipole Expansion | h = −5→5 |
| Tmin = 0.701, Tmax = 0.990 | k = −12→12 |
| 5628 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.056 | H-atom parameters not defined? |
| wR(F2) = 0.150 | Calculated w = 1/[σ2(Fo2) + (0.073P)2 + 0.1341P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 2046 reflections | Δρmax = 0.36 e Å−3 |
| 160 parameters | Δρmin = −0.41 e Å−3 |
| 8 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0303 (106) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O4 | −1.5645 (4) | 0.7799 (2) | 0.7444 (2) | 0.0188 (4) | |
| N1 | −1.1560 (5) | 0.5867 (2) | 0.7079 (2) | 0.0150 (4) | |
| O3 | −1.5460 (4) | 0.5754 (2) | 0.8597 (2) | 0.0192 (4) | |
| N3 | −1.4326 (5) | 0.6549 (2) | 0.7695 (2) | 0.0141 (4) | |
| O1 | −0.7652 (4) | 0.5940 (2) | 0.5549 (2) | 0.0195 (4) | |
| O2 | −1.1286 (4) | 0.7833 (2) | 0.5562 (2) | 0.0250 (5) | |
| N2 | −1.0196 (5) | 0.6627 (2) | 0.6019 (2) | 0.0146 (4) | |
| N6 | −0.5253 (5) | 1.3140 (2) | 0.7020 (2) | 0.0182 (5) | |
| N8 | −1.0239 (5) | 1.3129 (2) | 0.9107 (2) | 0.0183 (5) | |
| N4 | −0.6120 (5) | 1.1165 (2) | 0.8550 (2) | 0.0155 (4) | |
| C1 | −0.5118 (5) | 1.1720 (2) | 0.7385 (2) | 0.0142 (5) | |
| C2 | −0.8257 (6) | 1.1917 (2) | 0.9398 (2) | 0.0139 (5) | |
| N7 | −0.8490 (5) | 1.1378 (2) | 1.0607 (2) | 0.0174 (5) | |
| N5 | −0.3742 (5) | 1.0770 (2) | 0.6518 (2) | 0.0214 (5) | |
| H7B | −1.040 (5) | 1.171 (3) | 1.122 (2) | 0.029 (8)* | |
| H6A | −0.579 (8) | 1.387 (3) | 0.769 (2) | 0.043 (9)* | |
| H7A | −0.695 (7) | 1.052 (3) | 1.086 (3) | 0.050 (10)* | |
| H5A | −0.252 (6) | 1.108 (3) | 0.5696 (17) | 0.025 (7)* | |
| H8B | −1.180 (6) | 1.352 (3) | 0.984 (2) | 0.032 (8)* | |
| H8A | −1.038 (8) | 1.359 (3) | 0.8224 (15) | 0.037 (9)* | |
| H5B | −0.397 (8) | 0.9720 (15) | 0.673 (3) | 0.046 (10)* | |
| H6B | −0.448 (7) | 1.339 (3) | 0.6100 (13) | 0.026 (7)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O4 | 0.0201 (9) | 0.0070 (8) | 0.0257 (9) | 0.0059 (6) | 0.0012 (7) | −0.0016 (6) |
| N1 | 0.0150 (10) | 0.0090 (9) | 0.0179 (10) | 0.0036 (7) | 0.0024 (8) | −0.0004 (7) |
| O3 | 0.0214 (9) | 0.0127 (8) | 0.0207 (9) | −0.0004 (7) | 0.0047 (7) | −0.0011 (7) |
| N3 | 0.0159 (10) | 0.0097 (9) | 0.0149 (9) | 0.0023 (7) | 0.0001 (7) | −0.0023 (7) |
| O1 | 0.0175 (9) | 0.0146 (8) | 0.0220 (9) | 0.0053 (7) | 0.0048 (7) | −0.0016 (7) |
| O2 | 0.0291 (10) | 0.0122 (9) | 0.0262 (9) | 0.0083 (7) | 0.0056 (8) | 0.0068 (7) |
| N2 | 0.0173 (10) | 0.0111 (9) | 0.0138 (9) | 0.0014 (8) | −0.0005 (7) | −0.0013 (7) |
| N6 | 0.0253 (11) | 0.0095 (9) | 0.0168 (10) | 0.0014 (8) | 0.0037 (8) | −0.0008 (8) |
| N8 | 0.0192 (11) | 0.0130 (10) | 0.0188 (10) | 0.0063 (8) | 0.0004 (8) | 0.0010 (8) |
| N4 | 0.0189 (10) | 0.0086 (9) | 0.0163 (10) | 0.0026 (8) | 0.0015 (8) | 0.0002 (7) |
| C1 | 0.0161 (11) | 0.0080 (10) | 0.0171 (11) | 0.0022 (8) | −0.0012 (9) | −0.0006 (8) |
| C2 | 0.0156 (11) | 0.0084 (10) | 0.0176 (11) | −0.0009 (8) | −0.0010 (8) | −0.0026 (8) |
| N7 | 0.0197 (11) | 0.0129 (10) | 0.0163 (10) | 0.0049 (8) | 0.0023 (8) | −0.0021 (8) |
| N5 | 0.0319 (12) | 0.0095 (9) | 0.0184 (10) | 0.0029 (8) | 0.0046 (9) | −0.0004 (8) |
Geometric parameters (Å, º) top
| O4—N3 | 1.238 (2) | N6—C1 | 1.340 (3) |
| N1—N3 | 1.363 (2) | N8—C2 | 1.345 (3) |
| N1—N2 | 1.381 (3) | N4—C1 | 1.333 (3) |
| O3—N3 | 1.247 (2) | N4—C2 | 1.346 (3) |
| O1—N2 | 1.239 (2) | C1—N5 | 1.338 (3) |
| O2—N2 | 1.233 (3) | C2—N7 | 1.326 (3) |
| | | |
| N3—N1—N2 | 116.1 (2) | C1—N4—C2 | 123.2 (2) |
| O4—N3—O3 | 121.6 (2) | N4—C1—N5 | 116.8 (2) |
| O4—N3—N1 | 127.0 (2) | N4—C1—N6 | 126.0 (2) |
| O3—N3—N1 | 111.5 (2) | N5—C1—N6 | 117.2 (2) |
| O2—N2—O1 | 122.4 (2) | N7—C2—N8 | 117.9 (2) |
| O2—N2—N1 | 126.3 (2) | N7—C2—N4 | 116.7 (2) |
| O1—N2—N1 | 111.3 (2) | N8—C2—N4 | 125.3 (2) |
Crystal data top
| C2H8N8O4 | Z = 2 |
| Mr = 208.16 | F(000) = 216 |
| Triclinic, P1 | Dx = 1.668 Mg m−3 |
| a = 4.3114 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3227 (5) Å | Cell parameters from 2147 reflections |
| c = 10.5781 (6) Å | θ = 5.8–22.2° |
| α = 84.918 (1)° | µ = 0.15 mm−1 |
| β = 81.686 (2)° | T = 150 K |
| γ = 80.928 (2)° | Block, colourless |
| V = 414.50 (4) Å3 | 0.06mm × 0.15mm × 0.23mm mm |
Data collection top
Platform
diffractometer | 2053 independent reflections |
| Radiation source: fine focus sealed tube | 1375 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.054 |
| ω scans | θmax = 28.3°, θmin = 2.0° |
| Absorption correction: empirical :Multipole Expansion | h = −5→5 |
| Tmin = 0.725, Tmax = 0.990 | k = −12→12 |
| 5627 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.056 | H-atom parameters not defined? |
| wR(F2) = 0.150 | Calculated w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0292P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 2053 reflections | Δρmax = 0.33 e Å−3 |
| 160 parameters | Δρmin = −0.33 e Å−3 |
| 8 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0275 (108) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O4 | −1.5634 (4) | 0.7804 (2) | 0.7452 (2) | 0.0255 (4) | |
| N1 | −1.1565 (4) | 0.5873 (2) | 0.7080 (2) | 0.0199 (4) | |
| O3 | −1.5470 (4) | 0.5756 (2) | 0.8595 (2) | 0.0258 (4) | |
| N3 | −1.4325 (5) | 0.6555 (2) | 0.7697 (2) | 0.0188 (4) | |
| O1 | −0.7664 (4) | 0.5948 (2) | 0.5555 (2) | 0.0265 (4) | |
| O2 | −1.1280 (5) | 0.7838 (2) | 0.5577 (2) | 0.0349 (5) | |
| N2 | −1.0192 (5) | 0.6633 (2) | 0.6025 (2) | 0.0194 (4) | |
| N6 | −0.5251 (5) | 1.3145 (2) | 0.7025 (2) | 0.0244 (5) | |
| N8 | −1.0245 (5) | 1.3123 (2) | 0.9109 (2) | 0.0243 (5) | |
| N4 | −0.6112 (5) | 1.1173 (2) | 0.8554 (2) | 0.0208 (5) | |
| C1 | −0.5107 (5) | 1.1727 (2) | 0.7386 (2) | 0.0188 (5) | |
| C2 | −0.8266 (5) | 1.1918 (2) | 0.9398 (2) | 0.0182 (5) | |
| N7 | −0.8503 (5) | 1.1382 (2) | 1.0605 (2) | 0.0231 (5) | |
| N5 | −0.3751 (6) | 1.0782 (2) | 0.6521 (2) | 0.0286 (5) | |
| H7B | −1.043 (5) | 1.169 (3) | 1.122 (3) | 0.050 (9)* | |
| H6A | −0.568 (8) | 1.392 (3) | 0.766 (2) | 0.055 (10)* | |
| H7A | −0.694 (5) | 1.055 (2) | 1.086 (2) | 0.025 (7)* | |
| H5A | −0.248 (6) | 1.114 (3) | 0.5725 (18) | 0.038 (8)* | |
| H8B | −1.186 (6) | 1.354 (3) | 0.981 (2) | 0.047 (9)* | |
| H8A | −1.035 (7) | 1.353 (3) | 0.8210 (14) | 0.045 (9)* | |
| H5B | −0.382 (8) | 0.9718 (13) | 0.671 (3) | 0.053 (9)* | |
| H6B | −0.445 (7) | 1.342 (3) | 0.6116 (13) | 0.037 (8)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O4 | 0.0277 (9) | 0.0118 (8) | 0.0328 (9) | 0.0044 (7) | 0.0030 (7) | −0.0020 (7) |
| N1 | 0.0209 (10) | 0.0142 (9) | 0.0214 (10) | 0.0021 (8) | 0.0021 (8) | 0.0010 (7) |
| O3 | 0.0303 (9) | 0.0171 (8) | 0.0250 (9) | −0.0012 (7) | 0.0088 (7) | 0.0007 (7) |
| N3 | 0.0226 (10) | 0.0140 (9) | 0.0188 (9) | −0.0001 (8) | 0.0003 (8) | −0.0041 (7) |
| O1 | 0.0257 (9) | 0.0225 (9) | 0.0254 (9) | 0.0053 (7) | 0.0061 (7) | −0.0015 (7) |
| O2 | 0.0407 (11) | 0.0191 (9) | 0.0335 (10) | 0.0108 (8) | 0.0091 (8) | 0.0107 (8) |
| N2 | 0.0246 (10) | 0.0141 (9) | 0.0174 (9) | 0.0009 (8) | 0.0001 (8) | −0.0010 (7) |
| N6 | 0.0360 (12) | 0.0115 (9) | 0.0217 (10) | −0.0004 (8) | 0.0044 (9) | 0.0013 (8) |
| N8 | 0.0253 (11) | 0.0208 (10) | 0.0220 (10) | 0.0079 (9) | 0.0000 (8) | −0.0005 (8) |
| N4 | 0.0252 (10) | 0.0126 (9) | 0.0207 (10) | 0.0023 (8) | 0.0035 (8) | 0.0005 (7) |
| C1 | 0.0217 (11) | 0.0132 (10) | 0.0191 (11) | 0.0024 (9) | −0.0002 (9) | −0.0003 (8) |
| C2 | 0.0209 (11) | 0.0123 (10) | 0.0207 (11) | −0.0013 (9) | −0.0015 (9) | −0.0011 (8) |
| N7 | 0.0255 (11) | 0.0199 (10) | 0.0198 (10) | 0.0042 (9) | 0.0020 (8) | −0.0014 (8) |
| N5 | 0.0439 (13) | 0.0136 (10) | 0.0225 (10) | 0.0021 (9) | 0.0084 (9) | −0.0020 (8) |
Geometric parameters (Å, º) top
| O4—N3 | 1.234 (2) | N6—C1 | 1.338 (3) |
| N1—N3 | 1.363 (2) | N8—C2 | 1.340 (3) |
| N1—N2 | 1.378 (2) | N4—C1 | 1.336 (3) |
| O3—N3 | 1.247 (2) | N4—C2 | 1.345 (3) |
| O1—N2 | 1.234 (2) | C1—N5 | 1.334 (3) |
| O2—N2 | 1.228 (2) | C2—N7 | 1.325 (3) |
| | | |
| N3—N1—N2 | 116.2 (2) | C1—N4—C2 | 123.4 (2) |
| O4—N3—O3 | 121.4 (2) | N5—C1—N4 | 117.0 (2) |
| O4—N3—N1 | 127.0 (2) | N5—C1—N6 | 117.4 (2) |
| O3—N3—N1 | 111.5 (2) | N4—C1—N6 | 125.5 (2) |
| O2—N2—O1 | 122.6 (2) | N7—C2—N8 | 117.8 (2) |
| O2—N2—N1 | 125.9 (2) | N7—C2—N4 | 116.8 (2) |
| O1—N2—N1 | 111.5 (2) | N8—C2—N4 | 125.4 (2) |
Crystal data top
| C2H8N8O4 | Z = 2 |
| Mr = 208.16 | F(000) = 216 |
| Triclinic, P1 | Dx = 1.653 Mg m−3 |
| a = 4.3312 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3456 (5) Å | Cell parameters from 1916 reflections |
| c = 10.6220 (6) Å | θ = 5.8–17.6° |
| α = 84.541 (1)° | µ = 0.15 mm−1 |
| β = 81.285 (2)° | T = 200 K |
| γ = 80.632 (2)° | Block, colourless |
| V = 418.23 (4) Å3 | 0.06mm × 0.15mm × 0.23mm mm |
Data collection top
Platform
diffractometer | 2076 independent reflections |
| Radiation source: fine focus sealed tube | 1267 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.061 |
| ω scans | θmax = 28.3°, θmin = 1.9° |
| Absorption correction: empirical :Multipole Expansion | h = −5→5 |
| Tmin = 0.705, Tmax = 0.990 | k = −12→12 |
| 5689 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.058 | H-atom parameters not defined? |
| wR(F2) = 0.158 | Calculated w = 1/[σ2(Fo2) + (0.0781P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2076 reflections | Δρmax = 0.28 e Å−3 |
| 160 parameters | Δρmin = −0.34 e Å−3 |
| 8 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0179 (100) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O4 | −1.5610 (5) | 0.7807 (2) | 0.7458 (2) | 0.0351 (5) | |
| N1 | −1.1568 (5) | 0.5873 (2) | 0.7085 (2) | 0.0265 (5) | |
| O3 | −1.5476 (4) | 0.5757 (2) | 0.8594 (2) | 0.0348 (5) | |
| N3 | −1.4311 (5) | 0.6557 (2) | 0.7701 (2) | 0.0255 (5) | |
| O1 | −0.7674 (4) | 0.5962 (2) | 0.5555 (2) | 0.0358 (5) | |
| O2 | −1.1283 (5) | 0.7842 (2) | 0.5586 (2) | 0.0485 (6) | |
| N2 | −1.0190 (5) | 0.6637 (2) | 0.6027 (2) | 0.0262 (5) | |
| N6 | −0.5242 (6) | 1.3148 (2) | 0.7031 (2) | 0.0331 (6) | |
| N8 | −1.0254 (5) | 1.3120 (2) | 0.9108 (2) | 0.0322 (6) | |
| N4 | −0.6117 (5) | 1.1175 (2) | 0.8555 (2) | 0.0264 (5) | |
| C1 | −0.5111 (6) | 1.1737 (3) | 0.7390 (2) | 0.0249 (6) | |
| C2 | −0.8278 (6) | 1.1917 (3) | 0.9398 (2) | 0.0237 (5) | |
| N7 | −0.8499 (5) | 1.1376 (2) | 1.0601 (2) | 0.0308 (6) | |
| N5 | −0.3762 (6) | 1.0796 (2) | 0.6527 (2) | 0.0388 (6) | |
| H7B | −1.034 (5) | 1.173 (3) | 1.124 (2) | 0.044 (8)* | |
| H6A | −0.579 (8) | 1.392 (3) | 0.766 (2) | 0.068 (11)* | |
| H7A | −0.697 (5) | 1.051 (2) | 1.083 (2) | 0.032 (7)* | |
| H5A | −0.240 (7) | 1.115 (4) | 0.575 (2) | 0.060 (10)* | |
| H8B | −1.176 (6) | 1.352 (3) | 0.9842 (18) | 0.041 (8)* | |
| H8A | −1.045 (9) | 1.360 (4) | 0.8237 (17) | 0.070 (11)* | |
| H5B | −0.375 (8) | 0.9733 (14) | 0.676 (3) | 0.060 (10)* | |
| H6B | −0.434 (7) | 1.348 (3) | 0.6154 (15) | 0.045 (8)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O4 | 0.0361 (11) | 0.0182 (9) | 0.0445 (11) | 0.0043 (8) | 0.0062 (8) | −0.0017 (8) |
| N1 | 0.0277 (11) | 0.0179 (10) | 0.0285 (11) | 0.0029 (9) | 0.0044 (9) | 0.0013 (8) |
| O3 | 0.0387 (11) | 0.0256 (10) | 0.0336 (10) | −0.0025 (8) | 0.0112 (8) | 0.0018 (8) |
| N3 | 0.0275 (11) | 0.0196 (10) | 0.0278 (11) | −0.0017 (9) | −0.0003 (9) | −0.0033 (9) |
| O1 | 0.0331 (10) | 0.0308 (10) | 0.0339 (10) | 0.0071 (8) | 0.0111 (8) | 0.0013 (8) |
| O2 | 0.0551 (13) | 0.0279 (11) | 0.0450 (12) | 0.0137 (10) | 0.0167 (10) | 0.0146 (9) |
| N2 | 0.0320 (12) | 0.0201 (10) | 0.0238 (10) | −0.0014 (9) | 0.0010 (9) | 0.0000 (8) |
| N6 | 0.0482 (14) | 0.0172 (10) | 0.0287 (12) | −0.0030 (10) | 0.0061 (10) | 0.0024 (9) |
| N8 | 0.0298 (12) | 0.0283 (12) | 0.0311 (12) | 0.0099 (10) | 0.0012 (9) | 0.0012 (10) |
| N4 | 0.0337 (12) | 0.0172 (10) | 0.0239 (10) | 0.0008 (9) | 0.0039 (9) | 0.0006 (8) |
| C1 | 0.0289 (13) | 0.0180 (11) | 0.0248 (12) | 0.0009 (10) | −0.0004 (10) | 0.0008 (9) |
| C2 | 0.0267 (12) | 0.0162 (11) | 0.0273 (12) | −0.0043 (10) | −0.0017 (10) | 0.0007 (9) |
| N7 | 0.0375 (13) | 0.0229 (11) | 0.0257 (11) | 0.0051 (10) | 0.0044 (9) | −0.0008 (9) |
| N5 | 0.058 (2) | 0.0202 (11) | 0.0306 (12) | 0.0001 (11) | 0.0115 (11) | −0.0008 (9) |
Geometric parameters (Å, º) top
| O4—N3 | 1.233 (3) | N6—C1 | 1.332 (3) |
| N1—N3 | 1.358 (3) | N8—C2 | 1.338 (3) |
| N1—N2 | 1.383 (3) | N4—C1 | 1.335 (3) |
| O3—N3 | 1.247 (2) | N4—C2 | 1.346 (3) |
| O1—N2 | 1.228 (3) | C1—N5 | 1.334 (3) |
| O2—N2 | 1.227 (3) | C2—N7 | 1.325 (3) |
| | | |
| N3—N1—N2 | 116.1 (2) | C1—N4—C2 | 123.2 (2) |
| O4—N3—O3 | 121.3 (2) | N6—C1—N5 | 117.4 (2) |
| O4—N3—N1 | 127.0 (2) | N6—C1—N4 | 125.8 (2) |
| O3—N3—N1 | 111.7 (2) | N5—C1—N4 | 116.8 (2) |
| O2—N2—O1 | 122.5 (2) | N7—C2—N8 | 118.1 (2) |
| O2—N2—N1 | 125.6 (2) | N7—C2—N4 | 116.5 (2) |
| O1—N2—N1 | 111.8 (2) | N8—C2—N4 | 125.3 (2) |
Crystal data top
| C2H8N8O4 | Z = 2 |
| Mr = 208.16 | F(000) = 216 |
| Triclinic, P1 | Dx = 1.635 Mg m−3 |
| a = 4.3535 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.3742 (4) Å | Cell parameters from 1725 reflections |
| c = 10.6783 (4) Å | θ = 5.7–17.7° |
| α = 84.072 (1)° | µ = 0.15 mm−1 |
| β = 80.834 (2)° | T = 250 K |
| γ = 80.273 (2)° | Block, colourless |
| V = 422.73 (3) Å3 | 0.06mm × 0.15mm × 0.23mm mm |
Data collection top
Platform
diffractometer | 2091 independent reflections |
| Radiation source: fine focus sealed tube | 1190 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.060 |
| ω scans | θmax = 28.3°, θmin = 1.9° |
| Absorption correction: empirical :Multipole Expansion | h = −5→5 |
| Tmin = 0.573, Tmax = 0.978 | k = −12→12 |
| 5731 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.059 | H-atom parameters not defined? |
| wR(F2) = 0.154 | Calculated w = 1/[σ2(Fo2) + (0.0631P)2 + 0.1085P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 2091 reflections | Δρmax = 0.23 e Å−3 |
| 160 parameters | Δρmin = −0.27 e Å−3 |
| 8 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0284 (97) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O4 | −1.5591 (5) | 0.7813 (2) | 0.7467 (2) | 0.0440 (6) | |
| N1 | −1.1575 (5) | 0.5879 (2) | 0.7080 (2) | 0.0323 (5) | |
| O3 | −1.5482 (5) | 0.5760 (2) | 0.8589 (2) | 0.0436 (6) | |
| N3 | −1.4307 (5) | 0.6564 (2) | 0.7703 (2) | 0.0309 (5) | |
| O1 | −0.7693 (5) | 0.5976 (2) | 0.5561 (2) | 0.0474 (6) | |
| O2 | −1.1274 (6) | 0.7850 (2) | 0.5598 (2) | 0.0623 (8) | |
| N2 | −1.0202 (5) | 0.6651 (2) | 0.6032 (2) | 0.0330 (5) | |
| N6 | −0.5241 (6) | 1.3153 (2) | 0.7035 (2) | 0.0404 (6) | |
| N8 | −1.0251 (6) | 1.3123 (3) | 0.9110 (2) | 0.0407 (6) | |
| N4 | −0.6117 (5) | 1.1180 (2) | 0.8555 (2) | 0.0324 (6) | |
| C1 | −0.5107 (6) | 1.1744 (3) | 0.7394 (2) | 0.0306 (6) | |
| C2 | −0.8277 (6) | 1.1921 (3) | 0.9396 (2) | 0.0286 (6) | |
| N7 | −0.8495 (6) | 1.1377 (2) | 1.0596 (2) | 0.0371 (6) | |
| N5 | −0.3773 (7) | 1.0812 (3) | 0.6537 (2) | 0.0480 (7) | |
| H7B | −1.038 (5) | 1.172 (3) | 1.122 (2) | 0.054 (9)* | |
| H6A | −0.577 (8) | 1.392 (3) | 0.766 (2) | 0.064 (10)* | |
| H7A | −0.696 (6) | 1.050 (2) | 1.083 (3) | 0.061 (10)* | |
| H5A | −0.255 (6) | 1.109 (3) | 0.5703 (16) | 0.049 (9)* | |
| H8B | −1.185 (6) | 1.353 (3) | 0.982 (2) | 0.057 (9)* | |
| H8A | −1.033 (9) | 1.358 (4) | 0.8230 (15) | 0.072 (11)* | |
| H5B | −0.372 (9) | 0.9747 (13) | 0.676 (3) | 0.070 (11)* | |
| H6B | −0.419 (7) | 1.344 (4) | 0.6164 (16) | 0.060 (10)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O4 | 0.0433 (12) | 0.0253 (10) | 0.0550 (12) | 0.0050 (9) | 0.0069 (10) | −0.0024 (9) |
| N1 | 0.0343 (12) | 0.0259 (11) | 0.0312 (11) | −0.0003 (9) | 0.0038 (9) | 0.0021 (9) |
| O3 | 0.0484 (12) | 0.0339 (11) | 0.0405 (11) | −0.0055 (9) | 0.0128 (9) | 0.0028 (9) |
| N3 | 0.0327 (12) | 0.0263 (11) | 0.0313 (11) | −0.0029 (10) | 0.0023 (9) | −0.0045 (9) |
| O1 | 0.0437 (12) | 0.0424 (12) | 0.0430 (11) | 0.0065 (10) | 0.0147 (9) | 0.0031 (9) |
| O2 | 0.069 (2) | 0.0378 (12) | 0.0575 (14) | 0.0145 (11) | 0.0192 (12) | 0.0214 (11) |
| N2 | 0.0378 (13) | 0.0298 (12) | 0.0285 (11) | −0.0037 (10) | 0.0004 (10) | 0.0009 (9) |
| N6 | 0.060 (2) | 0.0213 (11) | 0.0344 (13) | −0.0054 (11) | 0.0066 (11) | 0.0034 (10) |
| N8 | 0.0395 (14) | 0.0370 (13) | 0.0375 (13) | 0.0097 (11) | −0.0002 (11) | 0.0009 (11) |
| N4 | 0.0395 (13) | 0.0215 (10) | 0.0310 (12) | −0.0016 (9) | 0.0045 (10) | 0.0019 (9) |
| C1 | 0.0345 (14) | 0.0238 (12) | 0.0304 (13) | −0.0011 (11) | −0.0008 (11) | −0.0002 (10) |
| C2 | 0.0310 (13) | 0.0216 (12) | 0.0319 (13) | −0.0045 (10) | −0.0019 (10) | 0.0006 (10) |
| N7 | 0.0397 (14) | 0.0338 (13) | 0.0298 (12) | 0.0048 (11) | 0.0049 (10) | 0.0016 (10) |
| N5 | 0.073 (2) | 0.0264 (12) | 0.0347 (13) | −0.0006 (12) | 0.0128 (12) | −0.0003 (10) |
Geometric parameters (Å, º) top
| O4—N3 | 1.228 (3) | N6—C1 | 1.331 (3) |
| N1—N3 | 1.360 (3) | N8—C2 | 1.337 (3) |
| N1—N2 | 1.377 (3) | N4—C1 | 1.334 (3) |
| O3—N3 | 1.246 (3) | N4—C2 | 1.346 (3) |
| O1—N2 | 1.226 (3) | C1—N5 | 1.327 (3) |
| O2—N2 | 1.217 (3) | C2—N7 | 1.324 (3) |
| | | |
| N3—N1—N2 | 116.0 (2) | C1—N4—C2 | 123.2 (2) |
| O4—N3—O3 | 121.3 (2) | N5—C1—N6 | 117.5 (2) |
| O4—N3—N1 | 127.0 (2) | N5—C1—N4 | 116.8 (2) |
| O3—N3—N1 | 111.7 (2) | N6—C1—N4 | 125.6 (2) |
| O2—N2—O1 | 122.5 (2) | N7—C2—N8 | 118.1 (2) |
| O2—N2—N1 | 125.9 (2) | N7—C2—N4 | 116.5 (2) |
| O1—N2—N1 | 111.6 (2) | N8—C2—N4 | 125.4 (2) |
Crystal data top
| C2H8N8O4 | Z = 2 |
| Mr = 208.16 | F(000) = 216 |
| P1 | Dx = 1.618 Mg m−3 |
| a = 4.3738 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.4027 (5) Å | Cell parameters from 1624 reflections |
| c = 10.7433 (6) Å | θ = 5.7–16.5° |
| α = 83.518 (2)° | µ = 0.15 mm−1 |
| β = 80.343 (2)° | T = 298 K |
| γ = 79.867 (2)° | Block, colourless |
| V = 427.18 (4) Å3 | 0.23mm × 0.15mm × 0.06mm mm |
Data collection top
Platform
diffractometer | 2111 independent reflections |
| Radiation source: fine focus sealed tube | 1070 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.070 |
| ω scans | θmax = 28.3°, θmin = 1.9° |
| Absorption correction: empirical :Multipole Expansion | h = −5→5 |
| Tmin = 0.535, Tmax = 0.990 | k = −12→12 |
| 5746 measured reflections | l = −14→14 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.069 | H-atom parameters not defined? |
| wR(F2) = 0.183 | Calculated w = 1/[σ2(Fo2) + (0.0819P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2111 reflections | Δρmax = 0.27 e Å−3 |
| 161 parameters | Δρmin = −0.31 e Å−3 |
| 8 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0379 (131) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O4 | −1.5569 (6) | 0.7818 (2) | 0.7474 (2) | 0.0572 (7) | |
| N1 | −1.1589 (6) | 0.5880 (2) | 0.7081 (2) | 0.0395 (7) | |
| O3 | −1.5488 (6) | 0.5768 (2) | 0.8586 (2) | 0.0560 (7) | |
| N3 | −1.4303 (6) | 0.6567 (3) | 0.7706 (2) | 0.0375 (6) | |
| O1 | −0.7715 (6) | 0.5993 (2) | 0.5562 (2) | 0.0615 (8) | |
| O2 | −1.1286 (7) | 0.7857 (3) | 0.5608 (3) | 0.0793 (10) | |
| N2 | −1.0219 (6) | 0.6663 (3) | 0.6041 (2) | 0.0415 (7) | |
| N6 | −0.5230 (7) | 1.3160 (3) | 0.7035 (3) | 0.0500 (8) | |
| N8 | −1.0253 (7) | 1.3121 (3) | 0.9111 (3) | 0.0497 (8) | |
| N4 | −0.6121 (6) | 1.1190 (2) | 0.8559 (2) | 0.0416 (7) | |
| C1 | −0.5133 (7) | 1.1754 (3) | 0.7406 (3) | 0.0387 (8) | |
| C2 | −0.8268 (7) | 1.1924 (3) | 0.9394 (3) | 0.0357 (7) | |
| N7 | −0.8503 (7) | 1.1384 (3) | 1.0589 (2) | 0.0475 (8) | |
| N5 | −0.3767 (8) | 1.0829 (3) | 0.6553 (3) | 0.0581 (9) | |
| H7B | −1.025 (6) | 1.170 (4) | 1.129 (3) | 0.071 (11)* | |
| H6A | −0.584 (9) | 1.390 (3) | 0.767 (3) | 0.069 (11)* | |
| H7A | −0.695 (6) | 1.051 (2) | 1.081 (3) | 0.055 (10)* | |
| H5A | −0.261 (8) | 1.118 (4) | 0.5722 (19) | 0.071 (11)* | |
| H8B | −1.180 (6) | 1.353 (3) | 0.984 (2) | 0.061 (10)* | |
| H8A | −1.044 (9) | 1.354 (4) | 0.8225 (15) | 0.070 (11)* | |
| H5B | −0.398 (10) | 0.9780 (16) | 0.676 (4) | 0.088 (13)* | |
| H6B | −0.419 (8) | 1.345 (4) | 0.6160 (17) | 0.074 (12)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O4 | 0.0580 (15) | 0.0288 (12) | 0.073 (2) | 0.0041 (10) | 0.0114 (13) | −0.0018 (10) |
| N1 | 0.0395 (15) | 0.0303 (13) | 0.0411 (14) | 0.0003 (11) | 0.0058 (12) | 0.0025 (10) |
| O3 | 0.064 (2) | 0.0399 (13) | 0.0526 (14) | −0.0074 (11) | 0.0180 (12) | 0.0036 (10) |
| N3 | 0.0412 (15) | 0.0284 (13) | 0.0396 (14) | −0.0034 (11) | 0.0013 (12) | −0.0035 (10) |
| O1 | 0.059 (2) | 0.0507 (14) | 0.056 (2) | 0.0075 (12) | 0.0188 (13) | 0.0060 (11) |
| O2 | 0.087 (2) | 0.0458 (15) | 0.075 (2) | 0.0174 (14) | 0.022 (2) | 0.0288 (13) |
| N2 | 0.046 (2) | 0.0318 (14) | 0.0404 (15) | −0.0012 (12) | 0.0037 (13) | 0.0019 (11) |
| N6 | 0.074 (2) | 0.0234 (13) | 0.044 (2) | −0.0045 (13) | 0.0065 (15) | 0.0042 (11) |
| N8 | 0.051 (2) | 0.043 (2) | 0.045 (2) | 0.0123 (13) | 0.0005 (14) | 0.0019 (12) |
| N4 | 0.053 (2) | 0.0252 (12) | 0.0369 (14) | 0.0017 (11) | 0.0069 (12) | 0.0051 (10) |
| C1 | 0.045 (2) | 0.0261 (15) | 0.040 (2) | 0.0011 (12) | −0.0003 (14) | 0.0010 (12) |
| C2 | 0.039 (2) | 0.0256 (14) | 0.040 (2) | −0.0061 (12) | −0.0019 (14) | 0.0009 (12) |
| N7 | 0.055 (2) | 0.039 (2) | 0.037 (2) | 0.0063 (13) | 0.0056 (13) | 0.0020 (12) |
| N5 | 0.088 (2) | 0.0286 (15) | 0.045 (2) | −0.0021 (14) | 0.015 (2) | −0.0002 (12) |
Geometric parameters (Å, º) top
| O4—N3 | 1.226 (3) | N6—C1 | 1.333 (4) |
| N1—N3 | 1.356 (3) | N8—C2 | 1.334 (4) |
| N1—N2 | 1.376 (3) | N4—C1 | 1.325 (3) |
| O3—N3 | 1.240 (3) | N4—C2 | 1.338 (4) |
| O1—N2 | 1.226 (3) | C1—N5 | 1.330 (4) |
| O2—N2 | 1.210 (3) | C2—N7 | 1.321 (4) |
| | | |
| N3—N1—N2 | 115.7 (2) | C1—N4—C2 | 123.1 (2) |
| O4—N3—O3 | 121.1 (2) | N4—C1—N5 | 117.0 (3) |
| O4—N3—N1 | 126.9 (2) | N4—C1—N6 | 126.3 (3) |
| O3—N3—N1 | 112.0 (2) | N5—C1—N6 | 116.6 (3) |
| O2—N2—O1 | 122.1 (2) | N7—C2—N8 | 117.6 (3) |
| O2—N2—N1 | 126.2 (2) | N7—C2—N4 | 116.9 (3) |
| O1—N2—N1 | 111.7 (2) | N8—C2—N4 | 125.5 (3) |
Crystal data top
| C2H9N11O8 | F(000) = 648 |
| Mr = 315.20 | Dx = 1.906 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.6824 (3) Å | Cell parameters from 2729 reflections |
| b = 8.145 Å | θ = 4.0–27.8° |
| c = 13.0023 (3) Å | µ = 0.18 mm−1 |
| β = 117.407 (1)° | T = 85 K |
| V = 1098.33 (4) Å3 | Block, colorless |
| Z = 4 | 0.22 × 0.21 × 0.20 mm |
Data collection top
Platform
diffractometer | 1364 independent reflections |
| Radiation source: fine focus sealed tube | 1158 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| ω scans | θmax = 28.3°, θmin = 3.2° |
| Absorption correction: empirical :Multipole Expansion | h = −14→15 |
| Tmin = 0.553, Tmax = 0.990 | k = −10→8 |
| 3661 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters not defined? |
| wR(F2) = 0.110 | Calculated w = 1/[σ2(Fo2) + (0.0672P)2 + 0.3387P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 1364 reflections | Δρmax = 0.31 e Å−3 |
| 115 parameters | Δρmin = −0.35 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0028 (13) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| N6 | 0.35892 (10) | −0.08803 (14) | 0.49058 (9) | 0.0111 (3) | |
| O2 | 0.37115 (9) | −0.23830 (11) | 0.50064 (8) | 0.0134 (3) | |
| N5 | 0.35512 (11) | −0.01707 (14) | 0.58679 (10) | 0.0114 (3) | |
| N4 | 0.37463 (10) | 0.14770 (14) | 0.59951 (9) | 0.0107 (3) | |
| O4 | 0.35754 (10) | 0.20270 (12) | 0.68117 (8) | 0.0158 (3) | |
| O3 | 0.40938 (10) | 0.23546 (11) | 0.54152 (9) | 0.0149 (3) | |
| O1 | 0.34446 (11) | −0.01211 (12) | 0.40407 (8) | 0.0175 (3) | |
| C1 | 0.42322 (12) | 0.4043 (2) | 0.29165 (10) | 0.0096 (3) | |
| N3 | 0.38270 (11) | 0.25228 (13) | 0.26696 (10) | 0.0121 (3) | |
| N2 | 0.38971 (11) | 0.49894 (13) | 0.35574 (10) | 0.0114 (3) | |
| N1 | 0.5000 | 0.4759 (2) | 0.2500 | 0.0144 (4) | |
| H2B | 0.3223 (15) | 0.465 (2) | 0.3763 (16) | 0.027 (5)* | |
| H1 | 0.5000 | 0.5977 (12) | 0.2500 | 0.032 (7)* | |
| H3B | 0.3897 (18) | 0.188 (2) | 0.2066 (13) | 0.027 (5)* | |
| H2A | 0.4295 (18) | 0.6075 (15) | 0.3855 (16) | 0.033 (5)* | |
| H3A | 0.3397 (18) | 0.203 (2) | 0.3097 (15) | 0.030 (5)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| N6 | 0.0117 (5) | 0.0121 (6) | 0.0085 (5) | −0.0020 (4) | 0.0037 (4) | −0.0010 (4) |
| O2 | 0.0161 (5) | 0.0088 (5) | 0.0149 (5) | −0.0006 (3) | 0.0068 (4) | −0.0011 (3) |
| N5 | 0.0172 (6) | 0.0091 (6) | 0.0091 (5) | −0.0017 (4) | 0.0071 (5) | −0.0012 (4) |
| N4 | 0.0104 (5) | 0.0113 (6) | 0.0090 (5) | −0.0007 (4) | 0.0031 (4) | 0.0004 (4) |
| O4 | 0.0210 (6) | 0.0155 (5) | 0.0131 (5) | −0.0011 (4) | 0.0097 (4) | −0.0044 (4) |
| O3 | 0.0201 (5) | 0.0121 (5) | 0.0132 (5) | −0.0044 (4) | 0.0081 (4) | 0.0023 (3) |
| O1 | 0.0272 (6) | 0.0172 (5) | 0.0076 (5) | −0.0024 (4) | 0.0075 (4) | 0.0017 (4) |
| C1 | 0.0106 (6) | 0.0118 (6) | 0.0051 (5) | 0.0021 (5) | 0.0023 (5) | 0.0019 (4) |
| N3 | 0.0143 (6) | 0.0112 (6) | 0.0117 (6) | −0.0020 (4) | 0.0067 (5) | −0.0030 (4) |
| N2 | 0.0147 (6) | 0.0106 (6) | 0.0109 (6) | −0.0009 (4) | 0.0076 (5) | −0.0020 (4) |
| N1 | 0.0239 (9) | 0.0084 (7) | 0.0185 (8) | 0.000 | 0.0162 (7) | 0.000 |
Geometric parameters (Å, º) top
| N6—O1 | 1.2252 (14) | N4—O4 | 1.2503 (14) |
| N6—O2 | 1.2322 (15) | C1—N3 | 1.312 (2) |
| N6—N5 | 1.3972 (15) | C1—N2 | 1.320 (2) |
| N5—N4 | 1.359 (2) | C1—N1 | 1.3729 (14) |
| N4—O3 | 1.2354 (14) | N1—C1i | 1.3729 (14) |
| | | |
| O1—N6—O2 | 123.99 (11) | O4—N4—N5 | 111.95 (10) |
| O1—N6—N5 | 124.43 (11) | N3—C1—N2 | 121.83 (12) |
| O2—N6—N5 | 111.45 (10) | N3—C1—N1 | 122.14 (12) |
| N4—N5—N6 | 116.42 (10) | N2—C1—N1 | 116.01 (12) |
| O3—N4—O4 | 122.47 (11) | C1—N1—C1i | 129.8 (2) |
| O3—N4—N5 | 125.53 (11) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
| C2H9N11O8 | F(000) = 648 |
| Mr = 315.20 | Dx = 1.900 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.7008 (8) Å | Cell parameters from 2700 reflections |
| b = 8.1485 (5) Å | θ = 4.0–27.4° |
| c = 13.0111 (9) Å | µ = 0.18 mm−1 |
| β = 117.337 (1)° | T = 100 K |
| V = 1101.99 (13) Å3 | Block, colorless |
| Z = 4 | 0.22 × 0.21 × 0.20 mm |
Data collection top
Platform
diffractometer | 1366 independent reflections |
| Radiation source: fine focus sealed tube | 1179 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| ω scans | θmax = 28.3°, θmin = 3.2° |
| Absorption correction: empirical :Multipole Expansion | h = −14→15 |
| Tmin = 0.611, Tmax = 0.990 | k = −10→8 |
| 3674 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters not defined? |
| wR(F2) = 0.110 | Calculated w = 1/[σ2(Fo2) + (0.062P)2 + 0.5501P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max = 0.004 |
| 1366 reflections | Δρmax = 0.30 e Å−3 |
| 115 parameters | Δρmin = −0.36 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0034 (13) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.42326 (13) | 0.4044 (2) | 0.29169 (11) | 0.0105 (3) | |
| N1 | 0.5000 | 0.4759 (2) | 0.2500 | 0.0158 (4) | |
| N2 | 0.38989 (12) | 0.49894 (14) | 0.35584 (10) | 0.0127 (3) | |
| N3 | 0.38288 (11) | 0.25232 (14) | 0.26722 (10) | 0.0133 (3) | |
| N4 | 0.37460 (11) | 0.14779 (15) | 0.59951 (10) | 0.0119 (3) | |
| N5 | 0.35492 (12) | −0.01705 (14) | 0.58687 (10) | 0.0127 (3) | |
| N6 | 0.35870 (11) | −0.08789 (14) | 0.49067 (9) | 0.0124 (3) | |
| O1 | 0.34419 (12) | −0.01201 (13) | 0.40409 (9) | 0.0201 (3) | |
| O2 | 0.37104 (10) | −0.23821 (12) | 0.50058 (9) | 0.0150 (3) | |
| O3 | 0.40940 (10) | 0.23540 (12) | 0.54146 (9) | 0.0169 (3) | |
| O4 | 0.35771 (10) | 0.20299 (13) | 0.68120 (9) | 0.0174 (3) | |
| H1 | 0.5000 | 0.5978 (13) | 0.2500 | 0.040 (8)* | |
| H2A | 0.4305 (18) | 0.6065 (15) | 0.3852 (16) | 0.030 (5)* | |
| H2B | 0.3213 (15) | 0.465 (2) | 0.3749 (17) | 0.029 (5)* | |
| H3A | 0.3386 (18) | 0.205 (2) | 0.3089 (16) | 0.031 (5)* | |
| H3B | 0.3892 (19) | 0.189 (2) | 0.2062 (13) | 0.029 (5)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0106 (6) | 0.0124 (6) | 0.0077 (6) | 0.0020 (5) | 0.0034 (5) | 0.0017 (5) |
| N1 | 0.0262 (9) | 0.0079 (8) | 0.0220 (9) | 0.000 | 0.0187 (8) | 0.000 |
| N2 | 0.0161 (6) | 0.0116 (6) | 0.0130 (6) | −0.0010 (4) | 0.0090 (5) | −0.0021 (4) |
| N3 | 0.0149 (6) | 0.0122 (6) | 0.0140 (6) | −0.0021 (4) | 0.0078 (5) | −0.0031 (4) |
| N4 | 0.0116 (5) | 0.0117 (6) | 0.0111 (5) | −0.0006 (4) | 0.0041 (4) | 0.0009 (4) |
| N5 | 0.0183 (6) | 0.0101 (6) | 0.0115 (6) | −0.0021 (4) | 0.0083 (5) | −0.0014 (4) |
| N6 | 0.0124 (6) | 0.0133 (6) | 0.0108 (5) | −0.0022 (4) | 0.0047 (4) | −0.0002 (4) |
| O1 | 0.0305 (6) | 0.0192 (6) | 0.0098 (5) | −0.0030 (4) | 0.0085 (4) | 0.0012 (4) |
| O2 | 0.0176 (5) | 0.0098 (5) | 0.0182 (5) | −0.0010 (4) | 0.0088 (4) | −0.0017 (4) |
| O3 | 0.0220 (5) | 0.0134 (5) | 0.0172 (5) | −0.0054 (4) | 0.0106 (4) | 0.0016 (4) |
| O4 | 0.0216 (6) | 0.0167 (5) | 0.0172 (5) | −0.0018 (4) | 0.0117 (4) | −0.0054 (4) |
Geometric parameters (Å, º) top
| C1—N3 | 1.312 (2) | N4—O4 | 1.2506 (15) |
| C1—N2 | 1.320 (2) | N4—N5 | 1.360 (2) |
| C1—N1 | 1.3736 (15) | N5—N6 | 1.397 (2) |
| N1—C1i | 1.3736 (15) | N6—O1 | 1.2266 (15) |
| N4—O3 | 1.2362 (15) | N6—O2 | 1.233 (2) |
| | | |
| N3—C1—N2 | 121.76 (12) | O4—N4—N5 | 111.96 (11) |
| N3—C1—N1 | 122.17 (13) | N4—N5—N6 | 116.30 (11) |
| N2—C1—N1 | 116.05 (12) | O1—N6—O2 | 123.84 (12) |
| C1—N1—C1i | 129.8 (2) | O1—N6—N5 | 124.50 (12) |
| O3—N4—O4 | 122.45 (12) | O2—N6—N5 | 111.53 (10) |
| O3—N4—N5 | 125.55 (11) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
| C2H9N11O8 | F(000) = 648 |
| Mr = 315.20 | Dx = 1.881 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.7551 (5) Å | Cell parameters from 2658 reflections |
| b = 8.1557 (3) Å | θ = 4.0–27.4° |
| c = 13.0302 (4) Å | µ = 0.18 mm−1 |
| β = 117.005 (1)° | T = 150 K |
| V = 1113.01 (7) Å3 | Block, colorless |
| Z = 4 | 0.22 × 0.21 × 0.20 mm |
Data collection top
Platform
diffractometer | 1382 independent reflections |
| Radiation source: fine focus sealed tube | 1169 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| ω scans | θmax = 28.3°, θmin = 3.2° |
| Absorption correction: empirical :Multipole Expansion | h = −14→15 |
| Tmin = 0.760, Tmax = 0.990 | k = −10→8 |
| 3723 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters not defined? |
| wR(F2) = 0.105 | Calculated w = 1/[σ2(Fo2) + (0.0578P)2 + 0.6566P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 1382 reflections | Δρmax = 0.28 e Å−3 |
| 115 parameters | Δρmin = −0.30 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0052 (13) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.42365 (12) | 0.4044 (2) | 0.29181 (10) | 0.0139 (3) | |
| N1 | 0.5000 | 0.4754 (2) | 0.2500 | 0.0207 (4) | |
| N2 | 0.39051 (11) | 0.49880 (13) | 0.35611 (10) | 0.0168 (3) | |
| N3 | 0.38360 (11) | 0.25225 (14) | 0.26764 (10) | 0.0176 (3) | |
| N4 | 0.37457 (10) | 0.14795 (14) | 0.59952 (9) | 0.0162 (3) | |
| N5 | 0.35450 (12) | −0.01672 (14) | 0.58695 (10) | 0.0177 (3) | |
| N6 | 0.35794 (10) | −0.08732 (14) | 0.49061 (9) | 0.0167 (3) | |
| O1 | 0.34253 (12) | −0.01174 (13) | 0.40410 (9) | 0.0287 (3) | |
| O2 | 0.37074 (10) | −0.23752 (12) | 0.50055 (9) | 0.0210 (3) | |
| O3 | 0.40975 (11) | 0.23485 (12) | 0.54175 (9) | 0.0238 (3) | |
| O4 | 0.35779 (10) | 0.20320 (13) | 0.68102 (9) | 0.0249 (3) | |
| H1 | 0.5000 | 0.5974 (13) | 0.2500 | 0.052 (9)* | |
| H2A | 0.4296 (18) | 0.6069 (15) | 0.3841 (16) | 0.037 (5)* | |
| H2B | 0.3242 (15) | 0.464 (2) | 0.3783 (16) | 0.036 (5)* | |
| H3A | 0.3385 (17) | 0.206 (2) | 0.3089 (15) | 0.036 (5)* | |
| H3B | 0.3914 (18) | 0.188 (2) | 0.2077 (12) | 0.032 (5)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0153 (6) | 0.0135 (6) | 0.0130 (6) | 0.0020 (5) | 0.0066 (5) | 0.0019 (5) |
| N1 | 0.0352 (10) | 0.0093 (7) | 0.0305 (9) | 0.000 | 0.0260 (8) | 0.000 |
| N2 | 0.0218 (6) | 0.0138 (6) | 0.0197 (6) | −0.0017 (4) | 0.0136 (5) | −0.0029 (4) |
| N3 | 0.0207 (6) | 0.0144 (6) | 0.0212 (6) | −0.0038 (4) | 0.0124 (5) | −0.0047 (4) |
| N4 | 0.0163 (5) | 0.0147 (6) | 0.0174 (5) | −0.0017 (4) | 0.0074 (4) | 0.0006 (4) |
| N5 | 0.0259 (6) | 0.0121 (6) | 0.0183 (6) | −0.0033 (4) | 0.0128 (5) | −0.0007 (4) |
| N6 | 0.0182 (6) | 0.0159 (6) | 0.0163 (5) | −0.0031 (4) | 0.0079 (4) | −0.0008 (4) |
| O1 | 0.0455 (7) | 0.0257 (6) | 0.0158 (5) | −0.0045 (5) | 0.0146 (5) | 0.0020 (4) |
| O2 | 0.0251 (5) | 0.0135 (5) | 0.0264 (5) | −0.0015 (4) | 0.0134 (4) | −0.0024 (4) |
| O3 | 0.0314 (6) | 0.0172 (5) | 0.0261 (5) | −0.0079 (4) | 0.0158 (5) | 0.0018 (4) |
| O4 | 0.0326 (6) | 0.0212 (6) | 0.0269 (6) | −0.0029 (4) | 0.0188 (5) | −0.0075 (4) |
Geometric parameters (Å, º) top
| C1—N3 | 1.314 (2) | N4—O4 | 1.2490 (15) |
| C1—N2 | 1.320 (2) | N4—N5 | 1.361 (2) |
| C1—N1 | 1.3720 (14) | N5—N6 | 1.3982 (15) |
| N1—C1i | 1.3720 (14) | N6—O1 | 1.2240 (14) |
| N4—O3 | 1.2339 (15) | N6—O2 | 1.234 (2) |
| | | |
| N3—C1—N2 | 121.75 (12) | O4—N4—N5 | 111.89 (11) |
| N3—C1—N1 | 122.12 (12) | N4—N5—N6 | 116.13 (10) |
| N2—C1—N1 | 116.12 (12) | O1—N6—O2 | 123.82 (12) |
| C1i—N1—C1 | 130.0 (2) | O1—N6—N5 | 124.54 (12) |
| O3—N4—O4 | 122.51 (12) | O2—N6—N5 | 111.50 (10) |
| O3—N4—N5 | 125.55 (11) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
| C2H9N11O8 | F(000) = 648 |
| Mr = 315.20 | Dx = 1.870 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.7973 (4) Å | Cell parameters from 2642 reflections |
| b = 8.1492 (3) Å | µ = 0.18 mm−1 |
| c = 13.0286 (3) Å | T = 200 K |
| β = 116.639 (1)° | Block, colorless |
| V = 1119.59 (6) Å3 | 0.22 × 0.21 × 0.20 mm |
| Z = 4 | |
Data collection top
Platform
diffractometer | 1396 independent reflections |
| Radiation source: fine focus sealed tube | 1154 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.031 |
| ω scans | θmax = 28.3°, θmin = 3.2° |
| Absorption correction: empirical :Multipole Expansion | h = −15→15 |
| Tmin = 0.519, Tmax = 0.990 | k = −10→8 |
| 3797 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.042 | H-atom parameters not defined? |
| wR(F2) = 0.127 | Calculated w = 1/[σ2(Fo2) + (0.0712P)2 + 0.6555P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 1396 reflections | Δρmax = 0.28 e Å−3 |
| 115 parameters | Δρmin = −0.29 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0053 (16) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.42418 (14) | 0.4042 (2) | 0.29208 (12) | 0.0169 (3) | |
| N1 | 0.5000 | 0.4753 (2) | 0.2500 | 0.0253 (5) | |
| N2 | 0.39127 (13) | 0.4986 (2) | 0.35646 (11) | 0.0211 (3) | |
| N3 | 0.38439 (13) | 0.2522 (2) | 0.26813 (12) | 0.0220 (3) | |
| N4 | 0.37453 (12) | 0.1479 (2) | 0.59967 (11) | 0.0203 (3) | |
| N5 | 0.35415 (14) | −0.0164 (2) | 0.58702 (11) | 0.0218 (3) | |
| N6 | 0.35698 (12) | −0.0869 (2) | 0.49049 (11) | 0.0213 (3) | |
| O1 | 0.34102 (15) | −0.0115 (2) | 0.40423 (10) | 0.0378 (4) | |
| O2 | 0.37056 (11) | −0.23684 (14) | 0.50053 (10) | 0.0271 (3) | |
| O3 | 0.40996 (13) | 0.23445 (15) | 0.54201 (11) | 0.0306 (3) | |
| O4 | 0.35823 (13) | 0.2035 (2) | 0.68118 (11) | 0.0320 (3) | |
| H1 | 0.5000 | 0.5981 (13) | 0.2500 | 0.058 (10)* | |
| H2A | 0.432 (2) | 0.6069 (16) | 0.3850 (18) | 0.042 (6)* | |
| H2B | 0.3234 (16) | 0.465 (3) | 0.3774 (19) | 0.044 (6)* | |
| H3A | 0.341 (2) | 0.203 (3) | 0.3109 (17) | 0.046 (6)* | |
| H3B | 0.392 (2) | 0.187 (2) | 0.2079 (14) | 0.038 (6)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0186 (7) | 0.0164 (7) | 0.0165 (6) | 0.0014 (5) | 0.0085 (5) | 0.0016 (5) |
| N1 | 0.0427 (12) | 0.0116 (9) | 0.0365 (11) | 0.000 | 0.0310 (10) | 0.000 |
| N2 | 0.0274 (7) | 0.0173 (7) | 0.0249 (7) | −0.0023 (5) | 0.0173 (6) | −0.0044 (5) |
| N3 | 0.0252 (7) | 0.0184 (7) | 0.0269 (7) | −0.0053 (5) | 0.0156 (6) | −0.0060 (5) |
| N4 | 0.0197 (6) | 0.0175 (7) | 0.0233 (7) | −0.0029 (5) | 0.0092 (5) | 0.0005 (5) |
| N5 | 0.0307 (7) | 0.0156 (7) | 0.0219 (7) | −0.0044 (5) | 0.0143 (6) | −0.0008 (5) |
| N6 | 0.0225 (7) | 0.0207 (7) | 0.0209 (6) | −0.0044 (5) | 0.0100 (5) | −0.0009 (5) |
| O1 | 0.0607 (10) | 0.0330 (8) | 0.0203 (6) | −0.0068 (6) | 0.0186 (6) | 0.0013 (5) |
| O2 | 0.0307 (7) | 0.0179 (6) | 0.0352 (7) | −0.0019 (5) | 0.0171 (5) | −0.0035 (4) |
| O3 | 0.0402 (7) | 0.0219 (6) | 0.0338 (7) | −0.0105 (5) | 0.0202 (6) | 0.0024 (5) |
| O4 | 0.0410 (7) | 0.0266 (7) | 0.0361 (7) | −0.0047 (5) | 0.0241 (6) | −0.0100 (5) |
Geometric parameters (Å, º) top
| C1—N3 | 1.311 (2) | N4—O4 | 1.246 (2) |
| C1—N2 | 1.319 (2) | N4—N5 | 1.357 (2) |
| C1—N1 | 1.370 (2) | N5—N6 | 1.397 (2) |
| N1—C1i | 1.370 (2) | N6—O1 | 1.219 (2) |
| N4—O3 | 1.232 (2) | N6—O2 | 1.232 (2) |
| | | |
| N3—C1—N2 | 121.76 (14) | O4—N4—N5 | 112.06 (12) |
| N3—C1—N1 | 122.20 (14) | N4—N5—N6 | 116.16 (12) |
| N2—C1—N1 | 116.03 (14) | O1—N6—O2 | 123.85 (14) |
| C1—N1—C1i | 129.9 (2) | O1—N6—N5 | 124.48 (14) |
| O3—N4—O4 | 122.38 (14) | O2—N6—N5 | 111.55 (12) |
| O3—N4—N5 | 125.50 (13) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
| C2H9N11O8 | F(000) = 648 |
| Mr = 315.20 | Dx = 1.859 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.8391 (9) Å | Cell parameters from 2518 reflections |
| b = 8.1392 (6) Å | θ = 4.0–23.3° |
| c = 13.0265 (10) Å | µ = 0.18 mm−1 |
| β = 116.225 (1)° | T = 250 K |
| V = 1126.04 (15) Å3 | Block, colorless |
| Z = 4 | 0.22 × 0.21 × 0.20 mm |
Data collection top
Platform
diffractometer | 1402 independent reflections |
| Radiation source: fine focus sealed tube | 1128 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| ω scans | θmax = 28.3°, θmin = 3.2° |
| Absorption correction: empirical :Multipole Expansion | h = −15→15 |
| Tmin = 0.625, Tmax = 0.990 | k = −10→8 |
| 3810 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters not defined? |
| wR(F2) = 0.138 | Calculated w = 1/[σ2(Fo2) + (0.0853P)2 + 0.3144P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 1402 reflections | Δρmax = 0.32 e Å−3 |
| 115 parameters | Δρmin = −0.32 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0052 (19) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.42459 (14) | 0.4041 (2) | 0.29229 (12) | 0.0210 (3) | |
| N1 | 0.5000 | 0.4751 (2) | 0.2500 | 0.0309 (5) | |
| N2 | 0.39198 (14) | 0.4987 (2) | 0.35683 (12) | 0.0269 (4) | |
| N3 | 0.38501 (13) | 0.2526 (2) | 0.26843 (12) | 0.0275 (4) | |
| N4 | 0.37436 (12) | 0.1478 (2) | 0.59969 (12) | 0.0258 (4) | |
| N5 | 0.35366 (14) | −0.0160 (2) | 0.58704 (12) | 0.0281 (4) | |
| N6 | 0.35626 (12) | −0.0866 (2) | 0.49072 (11) | 0.0269 (4) | |
| O1 | 0.3393 (2) | −0.0110 (2) | 0.40435 (11) | 0.0489 (5) | |
| O2 | 0.37022 (12) | −0.23616 (15) | 0.50034 (11) | 0.0350 (4) | |
| O3 | 0.40998 (14) | 0.23416 (15) | 0.54227 (12) | 0.0391 (4) | |
| O4 | 0.35841 (14) | 0.2039 (2) | 0.68119 (12) | 0.0415 (4) | |
| H1 | 0.5000 | 0.5981 (13) | 0.2500 | 0.070 (11)* | |
| H2A | 0.4291 (19) | 0.6095 (15) | 0.3813 (18) | 0.044 (6)* | |
| H2B | 0.3261 (15) | 0.465 (2) | 0.3796 (17) | 0.041 (6)* | |
| H3A | 0.344 (2) | 0.201 (3) | 0.3127 (17) | 0.049 (6)* | |
| H3B | 0.395 (2) | 0.186 (3) | 0.2099 (16) | 0.060 (7)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0244 (7) | 0.0213 (7) | 0.0189 (7) | 0.0027 (6) | 0.0110 (6) | 0.0022 (5) |
| N1 | 0.0500 (13) | 0.0156 (9) | 0.0454 (12) | 0.000 | 0.0378 (11) | 0.000 |
| N2 | 0.0353 (7) | 0.0236 (7) | 0.0301 (7) | −0.0023 (6) | 0.0221 (6) | −0.0051 (5) |
| N3 | 0.0320 (8) | 0.0236 (8) | 0.0329 (8) | −0.0070 (5) | 0.0198 (7) | −0.0077 (5) |
| N4 | 0.0259 (7) | 0.0226 (7) | 0.0295 (7) | −0.0040 (5) | 0.0128 (6) | −0.0003 (5) |
| N5 | 0.0402 (8) | 0.0213 (7) | 0.0270 (7) | −0.0062 (6) | 0.0185 (6) | −0.0013 (5) |
| N6 | 0.0294 (7) | 0.0282 (8) | 0.0241 (7) | −0.0064 (6) | 0.0127 (6) | −0.0017 (5) |
| O1 | 0.0785 (11) | 0.0436 (9) | 0.0242 (7) | −0.0098 (7) | 0.0223 (7) | 0.0015 (5) |
| O2 | 0.0398 (7) | 0.0248 (7) | 0.0435 (8) | −0.0021 (5) | 0.0212 (6) | −0.0051 (5) |
| O3 | 0.0515 (8) | 0.0288 (7) | 0.0426 (8) | −0.0140 (6) | 0.0261 (7) | 0.0026 (5) |
| O4 | 0.0534 (8) | 0.0360 (8) | 0.0457 (8) | −0.0069 (6) | 0.0315 (7) | −0.0138 (6) |
Geometric parameters (Å, º) top
| C1—N3 | 1.307 (2) | N4—O4 | 1.244 (2) |
| C1—N2 | 1.317 (2) | N4—N5 | 1.352 (2) |
| C1—N1 | 1.367 (2) | N5—N6 | 1.393 (2) |
| N1—C1i | 1.367 (2) | N6—O1 | 1.218 (2) |
| N4—O3 | 1.229 (2) | N6—O2 | 1.228 (2) |
| | | |
| N3—C1—N2 | 121.85 (14) | O4—N4—N5 | 112.21 (13) |
| N3—C1—N1 | 122.15 (14) | N4—N5—N6 | 116.20 (12) |
| N2—C1—N1 | 115.98 (14) | O1—N6—O2 | 123.69 (15) |
| C1i—N1—C1 | 130.0 (2) | O1—N6—N5 | 124.29 (15) |
| O3—N4—O4 | 122.12 (15) | O2—N6—N5 | 111.89 (13) |
| O3—N4—N5 | 125.61 (14) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
| C4H18N22O16 | F(000) = 648 |
| Mr = 630.40 | Dx = 1.843 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.8959 (6) Å | Cell parameters from 2399 reflections |
| b = 8.1349 (4) Å | θ = 4.0–23.3° |
| c = 13.0359 (5) Å | µ = 0.18 mm−1 |
| β = 115.806 (1)° | T = 298 K |
| V = 1135.70 (9) Å3 | Block, colorless |
| Z = 2 | 0.22 × 0.21 × 0.20 mm |
Data collection top
Platform
diffractometer | 1410 independent reflections |
| Radiation source: fine focus sealed tube | 1074 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.034 |
| ω scans | θmax = 28.3°, θmin = 3.1° |
| Absorption correction: empirical :Multipole Expansion | h = −15→15 |
| Tmin = 0.547, Tmax = 0.990 | k = −10→8 |
| 3838 measured reflections | l = −17→17 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters not defined? |
| wR(F2) = 0.143 | Calculated w = 1/[σ2(Fo2) + (0.0754P)2 + 0.8093P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 1410 reflections | Δρmax = 0.24 e Å−3 |
| 115 parameters | Δρmin = −0.26 e Å−3 |
| 5 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0057 (17) |
Special details top
Experimental. The decay correction was applied simultaneously with the absorption correction
in SADABS. No formal measure of the extent of decay is printed out by
this program. The final unit cell is obtained from the refinement of the XYZ
weighted centroids of reflections above 20 σ(I). |
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 ALL reflections except for 0 with very negative
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| C1 | 0.4250 (2) | 0.4038 (2) | 0.29249 (13) | 0.0252 (4) | |
| N1 | 0.5000 | 0.4751 (3) | 0.2500 | 0.0364 (6) | |
| N2 | 0.3928 (2) | 0.4985 (2) | 0.35731 (13) | 0.0329 (4) | |
| N3 | 0.38592 (15) | 0.2525 (2) | 0.26903 (14) | 0.0337 (4) | |
| N4 | 0.37446 (14) | 0.1479 (2) | 0.59986 (13) | 0.0321 (4) | |
| N5 | 0.3531 (2) | −0.0156 (2) | 0.58697 (13) | 0.0342 (4) | |
| N6 | 0.35553 (14) | −0.0859 (2) | 0.49067 (12) | 0.0332 (4) | |
| O1 | 0.3375 (2) | −0.0107 (2) | 0.40464 (13) | 0.0615 (6) | |
| O2 | 0.36998 (14) | −0.2354 (2) | 0.50037 (13) | 0.0437 (4) | |
| O3 | 0.4101 (2) | 0.2337 (2) | 0.54249 (14) | 0.0484 (5) | |
| O4 | 0.3587 (2) | 0.2041 (2) | 0.68129 (14) | 0.0523 (5) | |
| H1 | 0.5000 | 0.5980 (13) | 0.2500 | 0.084 (13)* | |
| H2A | 0.429 (2) | 0.6100 (17) | 0.382 (2) | 0.059 (7)* | |
| H2B | 0.3256 (17) | 0.461 (3) | 0.378 (2) | 0.050 (7)* | |
| H3A | 0.342 (2) | 0.207 (3) | 0.313 (2) | 0.073 (9)* | |
| H3B | 0.395 (3) | 0.190 (3) | 0.2080 (17) | 0.069 (8)* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| C1 | 0.0274 (8) | 0.0276 (8) | 0.0221 (8) | 0.0034 (7) | 0.0122 (6) | 0.0022 (6) |
| N1 | 0.0556 (15) | 0.0217 (10) | 0.0513 (14) | 0.000 | 0.0412 (13) | 0.000 |
| N2 | 0.0416 (9) | 0.0310 (8) | 0.0358 (9) | −0.0034 (7) | 0.0259 (7) | −0.0054 (6) |
| N3 | 0.0373 (9) | 0.0317 (9) | 0.0383 (9) | −0.0087 (7) | 0.0221 (7) | −0.0090 (6) |
| N4 | 0.0297 (8) | 0.0300 (8) | 0.0362 (9) | −0.0044 (6) | 0.0140 (7) | 0.0000 (6) |
| N5 | 0.0476 (10) | 0.0273 (8) | 0.0319 (8) | −0.0065 (7) | 0.0212 (7) | −0.0005 (6) |
| N6 | 0.0339 (8) | 0.0369 (9) | 0.0292 (8) | −0.0079 (7) | 0.0141 (7) | −0.0022 (6) |
| O1 | 0.0975 (15) | 0.0567 (11) | 0.0282 (8) | −0.0141 (9) | 0.0253 (9) | 0.0014 (7) |
| O2 | 0.0477 (9) | 0.0333 (8) | 0.0539 (9) | −0.0029 (6) | 0.0256 (8) | −0.0073 (6) |
| O3 | 0.0616 (10) | 0.0378 (8) | 0.0521 (9) | −0.0180 (7) | 0.0307 (8) | 0.0020 (6) |
| O4 | 0.0670 (11) | 0.0469 (9) | 0.0562 (10) | −0.0091 (8) | 0.0391 (9) | −0.0177 (7) |
Geometric parameters (Å, º) top
| C1—N3 | 1.305 (2) | N4—O4 | 1.243 (2) |
| C1—N2 | 1.318 (2) | N4—N5 | 1.350 (2) |
| C1—N1 | 1.367 (2) | N5—N6 | 1.392 (2) |
| N1—C1i | 1.367 (2) | N6—O1 | 1.212 (2) |
| N4—O3 | 1.225 (2) | N6—O2 | 1.227 (2) |
| | | |
| N3—C1—N2 | 121.9 (2) | O4—N4—N5 | 112.23 (15) |
| N3—C1—N1 | 122.3 (2) | N4—N5—N6 | 116.14 (14) |
| N2—C1—N1 | 115.8 (2) | O1—N6—O2 | 123.8 (2) |
| C1—N1—C1i | 129.8 (2) | O1—N6—N5 | 124.2 (2) |
| O3—N4—O4 | 122.2 (2) | O2—N6—N5 | 111.82 (15) |
| O3—N4—N5 | 125.5 (2) | | |
| Symmetry code: (i) −x+1, y, −z+1/2. |
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research papers
.N3O
, (BIGH)(DN), and biguanidinium bis-dinitramide C2H9N
.2N3O
