Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806023968/is2043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806023968/is2043Isup2.hkl |
CCDC reference: 618971
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.001 Å
- Disorder in solvent or counterion
- R factor = 0.055
- wR factor = 0.175
- Data-to-parameter ratio = 31.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O2W PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C7 H3 N2 O6
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C6H13N4+·C7H3N2O6−·H2O | Z = 2 |
Mr = 370.33 | F(000) = 388 |
Triclinic, P1 | Dx = 1.545 Mg m−3 |
Hall symbol: -P 1 | Melting point = 447–449 K |
a = 6.4118 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1042 (2) Å | Cell parameters from 7304 reflections |
c = 14.1521 (2) Å | θ = 1.5–32.5° |
α = 77.986 (1)° | µ = 0.13 mm−1 |
β = 80.464 (1)° | T = 297 K |
γ = 85.585 (1)° | Block, colourless |
V = 796.09 (2) Å3 | 0.55 × 0.43 × 0.33 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 7817 independent reflections |
Radiation source: fine-focus sealed tube | 5034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.2°, θmin = 3.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→15 |
Tmin = 0.855, Tmax = 0.959 | l = −24→23 |
23506 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.0892P] where P = (Fo2 + 2Fc2)/3 |
7817 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.30 e Å−3 |
6 restraints | Δρmin = −0.27 e Å−3 |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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) | |
O1 | 0.43154 (18) | −0.38653 (11) | −0.08514 (6) | 0.0558 (2) | |
O2 | 0.15356 (19) | −0.38930 (13) | 0.02469 (8) | 0.0647 (3) | |
O3 | 0.2353 (2) | −0.17461 (16) | 0.32250 (8) | 0.0815 (4) | |
O4 | 0.3126 (2) | 0.05258 (13) | 0.25324 (9) | 0.0736 (3) | |
O5 | 0.7460 (2) | −0.04214 (14) | 0.27708 (8) | 0.0774 (4) | |
O6 | 0.87437 (19) | 0.09736 (13) | 0.13601 (9) | 0.0713 (3) | |
N1 | 0.97302 (18) | 0.50746 (13) | 0.26680 (7) | 0.0483 (2) | |
N2 | 0.63081 (15) | 0.42901 (11) | 0.35801 (7) | 0.0422 (2) | |
N3 | 0.88444 (17) | 0.24770 (12) | 0.29802 (8) | 0.0473 (2) | |
H13 | 0.8970 | 0.1654 | 0.2742 | 0.063* | |
N4 | 0.94966 (15) | 0.35576 (11) | 0.43087 (6) | 0.03939 (19) | |
N5 | 0.31967 (16) | −0.08237 (12) | 0.25573 (7) | 0.0445 (2) | |
N6 | 0.33219 (17) | −0.35200 (11) | −0.01005 (7) | 0.0427 (2) | |
C1 | 0.43929 (16) | −0.26179 (10) | 0.04078 (6) | 0.03279 (18) | |
C2 | 0.33086 (16) | −0.22149 (11) | 0.12540 (7) | 0.03311 (18) | |
H14 | 0.1941 | −0.2513 | 0.1511 | 0.040* | |
C3 | 0.43754 (15) | −0.13443 (10) | 0.16951 (6) | 0.02987 (16) | |
C4 | 0.64301 (15) | −0.09009 (9) | 0.13470 (7) | 0.03028 (17) | |
C5 | 0.74401 (17) | −0.13498 (12) | 0.04996 (8) | 0.0383 (2) | |
H16 | 0.8818 | −0.1070 | 0.0247 | 0.046* | |
C6 | 0.64289 (18) | −0.22075 (12) | 0.00242 (7) | 0.0396 (2) | |
H15 | 0.7115 | −0.2500 | −0.0544 | 0.048* | |
C7 | 0.76525 (18) | −0.00361 (12) | 0.18672 (9) | 0.0422 (2) | |
C8 | 0.7469 (2) | 0.54779 (14) | 0.28691 (11) | 0.0548 (3) | |
H1 | 0.6881 | 0.5661 | 0.2264 | 0.066* | |
H2 | 0.7287 | 0.6400 | 0.3121 | 0.066* | |
C9 | 0.9993 (2) | 0.37293 (18) | 0.22652 (9) | 0.0552 (3) | |
H5 | 1.1486 | 0.3445 | 0.2134 | 0.066* | |
H6 | 0.9431 | 0.3914 | 0.1654 | 0.066* | |
C10 | 1.05861 (18) | 0.47735 (14) | 0.35931 (8) | 0.0428 (2) | |
H3 | 1.0433 | 0.5680 | 0.3861 | 0.051* | |
H4 | 1.2084 | 0.4499 | 0.3470 | 0.051* | |
C11 | 0.65298 (18) | 0.29509 (14) | 0.31808 (9) | 0.0431 (2) | |
H9 | 0.5930 | 0.3137 | 0.2579 | 0.052* | |
H10 | 0.5768 | 0.2153 | 0.3639 | 0.052* | |
C12 | 0.72427 (18) | 0.39986 (16) | 0.44840 (8) | 0.0449 (2) | |
H7 | 0.7069 | 0.4897 | 0.4761 | 0.054* | |
H8 | 0.6499 | 0.3204 | 0.4954 | 0.054* | |
C13 | 0.9729 (2) | 0.22039 (14) | 0.39256 (11) | 0.0525 (3) | |
H11 | 0.8983 | 0.1408 | 0.4394 | 0.063* | |
H12 | 1.1214 | 0.1889 | 0.3814 | 0.063* | |
O1W | 0.7083 (4) | −0.1730 (3) | 0.46307 (15) | 0.0747 (9) | 0.574 (5) |
H1W1 | 0.7142 (4) | −0.1332 (5) | 0.4040 (7) | 0.112* | 0.574 (5) |
H2W1 | 0.8204 (13) | −0.2200 (6) | 0.4759 (2) | 0.112* | 0.574 (5) |
O2W | 0.5973 (7) | −0.0726 (5) | 0.4858 (2) | 0.0929 (15) | 0.426 (5) |
H1W2 | 0.6332 (8) | −0.0772 (5) | 0.4244 (7) | 0.139* | 0.426 (5) |
H2W2 | 0.4724 (16) | −0.0315 (6) | 0.4876 (2) | 0.139* | 0.426 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0820 (7) | 0.0545 (5) | 0.0415 (4) | 0.0017 (4) | −0.0243 (4) | −0.0235 (4) |
O2 | 0.0699 (7) | 0.0725 (7) | 0.0610 (6) | −0.0336 (5) | −0.0188 (5) | −0.0164 (5) |
O3 | 0.0982 (9) | 0.0937 (9) | 0.0493 (5) | −0.0385 (7) | 0.0284 (6) | −0.0255 (6) |
O4 | 0.0886 (8) | 0.0576 (6) | 0.0790 (7) | 0.0109 (5) | 0.0046 (6) | −0.0421 (5) |
O5 | 0.1199 (10) | 0.0687 (7) | 0.0593 (6) | −0.0141 (7) | −0.0462 (6) | −0.0192 (5) |
O6 | 0.0656 (6) | 0.0677 (6) | 0.0903 (8) | −0.0354 (5) | 0.0069 (5) | −0.0407 (6) |
N1 | 0.0552 (6) | 0.0552 (6) | 0.0361 (4) | −0.0219 (5) | −0.0065 (4) | −0.0063 (4) |
N2 | 0.0327 (4) | 0.0477 (5) | 0.0483 (5) | 0.0067 (3) | −0.0104 (3) | −0.0137 (4) |
N3 | 0.0460 (5) | 0.0471 (5) | 0.0588 (6) | −0.0020 (4) | −0.0075 (4) | −0.0333 (4) |
N4 | 0.0364 (4) | 0.0507 (5) | 0.0344 (4) | 0.0017 (4) | −0.0107 (3) | −0.0132 (3) |
N5 | 0.0424 (5) | 0.0545 (5) | 0.0405 (4) | −0.0035 (4) | 0.0012 (3) | −0.0237 (4) |
N6 | 0.0598 (6) | 0.0377 (4) | 0.0370 (4) | −0.0077 (4) | −0.0201 (4) | −0.0095 (3) |
C1 | 0.0435 (5) | 0.0292 (4) | 0.0291 (4) | −0.0042 (3) | −0.0108 (3) | −0.0084 (3) |
C2 | 0.0337 (4) | 0.0342 (4) | 0.0332 (4) | −0.0066 (3) | −0.0053 (3) | −0.0085 (3) |
C3 | 0.0337 (4) | 0.0287 (4) | 0.0284 (3) | −0.0011 (3) | −0.0036 (3) | −0.0093 (3) |
C4 | 0.0342 (4) | 0.0246 (3) | 0.0340 (4) | −0.0025 (3) | −0.0061 (3) | −0.0090 (3) |
C5 | 0.0364 (5) | 0.0390 (5) | 0.0408 (5) | −0.0087 (4) | 0.0023 (4) | −0.0149 (4) |
C6 | 0.0474 (6) | 0.0406 (5) | 0.0328 (4) | −0.0061 (4) | 0.0006 (4) | −0.0154 (4) |
C7 | 0.0392 (5) | 0.0374 (5) | 0.0587 (6) | 0.0011 (4) | −0.0149 (4) | −0.0246 (4) |
C8 | 0.0660 (8) | 0.0395 (6) | 0.0608 (7) | 0.0023 (5) | −0.0277 (6) | −0.0018 (5) |
C9 | 0.0503 (7) | 0.0863 (10) | 0.0362 (5) | −0.0194 (6) | 0.0040 (4) | −0.0310 (6) |
C10 | 0.0394 (5) | 0.0542 (6) | 0.0420 (5) | −0.0108 (4) | −0.0070 (4) | −0.0219 (4) |
C11 | 0.0371 (5) | 0.0513 (6) | 0.0453 (5) | −0.0106 (4) | −0.0111 (4) | −0.0123 (4) |
C12 | 0.0376 (5) | 0.0636 (7) | 0.0355 (5) | 0.0017 (5) | 0.0001 (4) | −0.0202 (5) |
C13 | 0.0484 (7) | 0.0423 (6) | 0.0694 (8) | 0.0105 (5) | −0.0197 (6) | −0.0131 (5) |
O1W | 0.0642 (13) | 0.0999 (19) | 0.0502 (10) | 0.0065 (12) | −0.0096 (8) | 0.0042 (10) |
O2W | 0.111 (3) | 0.089 (3) | 0.0626 (18) | −0.009 (2) | −0.0009 (17) | 0.0137 (16) |
O1—N6 | 1.2319 (14) | C2—H14 | 0.9300 |
O2—N6 | 1.2135 (15) | C3—C4 | 1.3876 (13) |
O3—N5 | 1.2086 (15) | C4—C5 | 1.3895 (13) |
O4—N5 | 1.2193 (14) | C4—C7 | 1.5177 (13) |
O5—C7 | 1.2414 (17) | C5—C6 | 1.3871 (14) |
O6—C7 | 1.2279 (16) | C5—H16 | 0.9300 |
N1—C9 | 1.4424 (18) | C6—H15 | 0.9300 |
N1—C8 | 1.4639 (19) | C8—H1 | 0.9700 |
N1—C10 | 1.4683 (15) | C8—H2 | 0.9700 |
N2—C11 | 1.4351 (16) | C9—H5 | 0.9700 |
N2—C12 | 1.4677 (15) | C9—H6 | 0.9700 |
N2—C8 | 1.4692 (17) | C10—H3 | 0.9700 |
N3—C13 | 1.5048 (18) | C10—H4 | 0.9700 |
N3—C9 | 1.5060 (18) | C11—H9 | 0.9700 |
N3—C11 | 1.5107 (16) | C11—H10 | 0.9700 |
N3—H13 | 0.88 | C12—H7 | 0.9700 |
N4—C13 | 1.4346 (16) | C12—H8 | 0.9700 |
N4—C12 | 1.4645 (15) | C13—H11 | 0.9700 |
N4—C10 | 1.4686 (15) | C13—H12 | 0.9700 |
N5—C3 | 1.4713 (12) | O1W—H1W1 | 0.835 (10) |
N6—C1 | 1.4697 (12) | O1W—H2W1 | 0.834 (8) |
C1—C6 | 1.3763 (15) | O2W—H1W2 | 0.870 (10) |
C1—C2 | 1.3856 (13) | O2W—H2W2 | 0.856 (11) |
C2—C3 | 1.3845 (13) | ||
C9—N1—C8 | 108.96 (10) | O6—C7—C4 | 117.38 (11) |
C9—N1—C10 | 109.01 (11) | O5—C7—C4 | 116.70 (10) |
C8—N1—C10 | 108.51 (10) | N1—C8—N2 | 111.96 (9) |
C11—N2—C12 | 109.20 (9) | N1—C8—H1 | 109.2 |
C11—N2—C8 | 108.45 (10) | N2—C8—H1 | 109.2 |
C12—N2—C8 | 108.72 (10) | N1—C8—H2 | 109.2 |
C13—N3—C9 | 109.22 (9) | N2—C8—H2 | 109.2 |
C13—N3—C11 | 108.43 (9) | H1—C8—H2 | 107.9 |
C9—N3—C11 | 108.83 (10) | N1—C9—N3 | 109.50 (9) |
C13—N3—H13 | 110.4 | N1—C9—H5 | 109.8 |
C9—N3—H13 | 110.7 | N3—C9—H5 | 109.8 |
C11—N3—H13 | 109.3 | N1—C9—H6 | 109.8 |
C13—N4—C12 | 108.76 (9) | N3—C9—H6 | 109.8 |
C13—N4—C10 | 109.91 (9) | H5—C9—H6 | 108.2 |
C12—N4—C10 | 108.27 (10) | N1—C10—N4 | 111.64 (8) |
O3—N5—O4 | 124.99 (11) | N1—C10—H3 | 109.3 |
O3—N5—C3 | 118.38 (10) | N4—C10—H3 | 109.3 |
O4—N5—C3 | 116.62 (10) | N1—C10—H4 | 109.3 |
O2—N6—O1 | 124.09 (10) | N4—C10—H4 | 109.3 |
O2—N6—C1 | 118.44 (10) | H3—C10—H4 | 108.0 |
O1—N6—C1 | 117.47 (10) | N2—C11—N3 | 109.69 (8) |
C6—C1—C2 | 122.71 (8) | N2—C11—H9 | 109.7 |
C6—C1—N6 | 118.72 (9) | N3—C11—H9 | 109.7 |
C2—C1—N6 | 118.57 (9) | N2—C11—H10 | 109.7 |
C3—C2—C1 | 116.26 (8) | N3—C11—H10 | 109.7 |
C3—C2—H14 | 121.9 | H9—C11—H10 | 108.2 |
C1—C2—H14 | 121.9 | N4—C12—N2 | 111.72 (8) |
C2—C3—C4 | 123.74 (8) | N4—C12—H7 | 109.3 |
C2—C3—N5 | 116.92 (8) | N2—C12—H7 | 109.3 |
C4—C3—N5 | 119.29 (8) | N4—C12—H8 | 109.3 |
C3—C4—C5 | 117.29 (8) | N2—C12—H8 | 109.3 |
C3—C4—C7 | 123.74 (8) | H7—C12—H8 | 107.9 |
C5—C4—C7 | 118.88 (9) | N4—C13—N3 | 109.60 (9) |
C6—C5—C4 | 121.13 (9) | N4—C13—H11 | 109.8 |
C6—C5—H16 | 119.4 | N3—C13—H11 | 109.8 |
C4—C5—H16 | 119.4 | N4—C13—H12 | 109.8 |
C1—C6—C5 | 118.85 (9) | N3—C13—H12 | 109.8 |
C1—C6—H15 | 120.6 | H11—C13—H12 | 108.2 |
C5—C6—H15 | 120.6 | H1W1—O1W—H2W1 | 112.9 (4) |
O6—C7—O5 | 125.92 (11) | H1W2—O2W—H2W2 | 102.8 (6) |
O2—N6—C1—C6 | 179.19 (11) | C9—N1—C8—N2 | 60.71 (13) |
O1—N6—C1—C6 | 0.03 (14) | C10—N1—C8—N2 | −57.86 (13) |
O2—N6—C1—C2 | −0.85 (15) | C11—N2—C8—N1 | −61.00 (13) |
O1—N6—C1—C2 | 179.99 (9) | C12—N2—C8—N1 | 57.63 (13) |
C6—C1—C2—C3 | 1.01 (14) | C8—N1—C9—N3 | −58.91 (13) |
N6—C1—C2—C3 | −178.95 (8) | C10—N1—C9—N3 | 59.34 (13) |
C1—C2—C3—C4 | −1.33 (14) | C13—N3—C9—N1 | −59.33 (14) |
C1—C2—C3—N5 | 176.10 (9) | C11—N3—C9—N1 | 58.87 (13) |
O3—N5—C3—C2 | 53.26 (15) | C9—N1—C10—N4 | −59.88 (12) |
O4—N5—C3—C2 | −125.72 (12) | C8—N1—C10—N4 | 58.66 (13) |
O3—N5—C3—C4 | −129.19 (13) | C13—N4—C10—N1 | 59.59 (13) |
O4—N5—C3—C4 | 51.83 (15) | C12—N4—C10—N1 | −59.09 (12) |
C2—C3—C4—C5 | 0.88 (14) | C12—N2—C11—N3 | −58.73 (12) |
N5—C3—C4—C5 | −176.50 (9) | C8—N2—C11—N3 | 59.59 (12) |
C2—C3—C4—C7 | −175.72 (9) | C13—N3—C11—N2 | 59.12 (12) |
N5—C3—C4—C7 | 6.91 (14) | C9—N3—C11—N2 | −59.58 (11) |
C3—C4—C5—C6 | −0.06 (15) | C13—N4—C12—N2 | −60.63 (13) |
C7—C4—C5—C6 | 176.71 (10) | C10—N4—C12—N2 | 58.77 (12) |
C2—C1—C6—C5 | −0.27 (16) | C11—N2—C12—N4 | 60.07 (13) |
N6—C1—C6—C5 | 179.68 (9) | C8—N2—C12—N4 | −58.09 (13) |
C4—C5—C6—C1 | −0.23 (17) | C12—N4—C13—N3 | 60.17 (13) |
C3—C4—C7—O6 | −139.59 (12) | C10—N4—C13—N3 | −58.20 (13) |
C5—C4—C7—O6 | 43.87 (15) | C9—N3—C13—N4 | 58.56 (13) |
C3—C4—C7—O5 | 40.66 (16) | C11—N3—C13—N4 | −59.89 (13) |
C5—C4—C7—O5 | −135.89 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O5 | 0.84 (1) | 1.80 (1) | 2.633 (2) | 176 (1) |
O2W—H1W2···O5 | 0.87 (1) | 2.06 (1) | 2.912 (3) | 167 (1) |
N3—H13···O5 | 0.88 | 2.18 | 2.935 (2) | 144 |
N3—H13···O6 | 0.88 | 2.20 | 2.916 (2) | 138 |
O1W—H2W1···N4i | 0.83 (1) | 2.26 (1) | 3.053 (3) | 158 (1) |
C11—H9···O1ii | 0.97 | 2.42 | 3.352 (2) | 159 |
C13—H12···O4iii | 0.97 | 2.51 | 3.207 (2) | 128 |
C13—H12···O1Wi | 0.97 | 2.59 | 3.069 (3) | 110 |
C5—H16···O6iv | 0.93 | 2.53 | 3.264 (2) | 136 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, −y, −z; (iii) x+1, y, z; (iv) −x+2, −y, −z. |
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