Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020612/er2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020612/er2026Isup2.hkl |
CCDC reference: 651381
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.070
- Data-to-parameter ratio = 8.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT708_ALERT_1_B D-H..A Calc 162(4), Rep 152(5), Dev.. 2.50 Sigma O8 -H8B -O2 1.555 1.555 1.655
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - C10 .. 5.54 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT706_ALERT_1_C H...A Calc 2.42(4), Rep 2.35(4), Dev.. 1.75 Sigma H7B -O1 1.555 1.555 PLAT706_ALERT_1_C H...A Calc 2.51(4), Rep 2.57(5), Dev.. 1.50 Sigma H7B -O8 1.555 1.455 PLAT706_ALERT_1_C H...A Calc 1.93(3), Rep 1.97(3), Dev.. 1.33 Sigma H8B -O2 1.555 1.655 PLAT707_ALERT_1_C D...A Calc 3.191(4), Rep 3.186(4), Dev.. 1.25 Sigma O7 -O8 1.555 1.455 PLAT708_ALERT_1_C D-H..A Calc 134(4), Rep 142(5), Dev.. 2.00 Sigma O7 -H7B -O1 1.555 1.555 1.555 PLAT708_ALERT_1_C D-H..A Calc 137(4), Rep 129(5), Dev.. 2.00 Sigma O7 -H7B -O8 1.555 1.555 1.455 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.60 From the CIF: _reflns_number_total 1762 Count of symmetry unique reflns 1779 Completeness (_total/calc) 99.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).
C6H15N4O2+·C4H3O4−·2H2O | Z = 1 |
Mr = 326.32 | F(000) = 174 |
Triclinic, P1 | Dx = 1.413 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2710 (1) Å | Cell parameters from 2145 reflections |
b = 8.0481 (2) Å | θ = 4.0–27.3° |
c = 9.7942 (2) Å | µ = 0.12 mm−1 |
α = 106.155 (1)° | T = 293 K |
β = 97.265 (1)° | Ball, colourless |
γ = 101.649 (2)° | 0.25 × 0.23 × 0.19 mm |
V = 383.42 (2) Å3 |
Bruker APEX II CCD detector diffractometer | 1762 independent reflections |
Radiation source: fine-focus sealed tube | 1697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
φ and ω scans | θmax = 27.6°, θmin = 2.9° |
Absorption correction: multi-scan (APEX2 Software Suite; Bruker, 2005) | h = −6→6 |
Tmin = 0.971, Tmax = 0.977 | k = −10→10 |
3711 measured reflections | l = −11→12 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0307P)2 + 0.0785P] where P = (Fo2 + 2Fc2)/3 |
1762 reflections | (Δ/σ)max = 0.003 |
220 parameters | Δρmax = 0.16 e Å−3 |
7 restraints | Δρmin = −0.17 e Å−3 |
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 | ||
C1 | 0.5124 (4) | 0.2367 (3) | 1.1719 (2) | 0.0340 (4) | |
N3 | 0.4360 (3) | 0.2303 (2) | 1.03538 (19) | 0.0371 (4) | |
H3 | 0.5434 | 0.2894 | 0.9964 | 0.045* | |
C2 | 0.1777 (4) | 0.1272 (3) | 0.9496 (2) | 0.0328 (4) | |
H2C | 0.0443 | 0.1862 | 0.9844 | 0.039* | |
H2D | 0.1402 | 0.0100 | 0.9625 | 0.039* | |
C3 | 0.1611 (4) | 0.1056 (3) | 0.7893 (2) | 0.0361 (4) | |
H3B | 0.1615 | 0.2190 | 0.7727 | 0.043* | |
H3A | 0.3128 | 0.0672 | 0.7575 | 0.043* | |
C4 | −0.0919 (4) | −0.0327 (3) | 0.7043 (2) | 0.0338 (4) | |
H4B | −0.2383 | 0.0017 | 0.7458 | 0.041* | |
H4A | −0.0821 | −0.1463 | 0.7177 | 0.041* | |
C5 | −0.1544 (3) | −0.0604 (3) | 0.5413 (2) | 0.0309 (4) | |
H5 | −0.3139 | −0.1580 | 0.4988 | 0.037* | |
C6 | −0.2084 (4) | 0.1066 (3) | 0.5100 (2) | 0.0322 (4) | |
C10 | 0.6354 (4) | 0.7889 (3) | 0.1320 (3) | 0.0430 (5) | |
C9 | 0.4657 (5) | 0.7478 (3) | −0.0122 (2) | 0.0419 (5) | |
H9 | 0.5449 | 0.7996 | −0.0751 | 0.050* | |
C8 | 0.2192 (4) | 0.6491 (3) | −0.0667 (2) | 0.0397 (5) | |
H8 | 0.1538 | 0.6440 | −0.1610 | 0.048* | |
C7 | 0.0314 (4) | 0.5456 (3) | −0.0001 (2) | 0.0377 (4) | |
N1 | 0.7486 (4) | 0.3327 (3) | 1.2460 (2) | 0.0459 (5) | |
H1A | 0.7976 | 0.3352 | 1.3339 | 0.055* | |
H1B | 0.8535 | 0.3926 | 1.2064 | 0.055* | |
N2 | 0.3535 (4) | 0.1452 (3) | 1.2346 (2) | 0.0465 (5) | |
H2A | 0.4045 | 0.1487 | 1.3225 | 0.056* | |
H2B | 0.1992 | 0.0823 | 1.1874 | 0.056* | |
N4 | 0.0642 (3) | −0.1117 (2) | 0.46877 (18) | 0.0352 (4) | |
H4AA | 0.2068 | −0.0204 | 0.4995 | 0.053* | |
H4BB | 0.0140 | −0.1399 | 0.3732 | 0.053* | |
H4CC | 0.1020 | −0.2054 | 0.4905 | 0.053* | |
O1 | −0.0316 (3) | 0.2044 (2) | 0.47618 (19) | 0.0465 (4) | |
O2 | −0.4342 (3) | 0.1313 (2) | 0.52342 (17) | 0.0392 (3) | |
O3 | 0.1045 (3) | 0.5427 (3) | 0.12759 (19) | 0.0522 (4) | |
O4 | −0.1896 (3) | 0.4639 (2) | −0.07398 (19) | 0.0510 (4) | |
O5 | 0.8595 (4) | 0.8837 (3) | 0.1586 (2) | 0.0620 (5) | |
O6 | 0.5485 (4) | 0.7220 (3) | 0.2274 (2) | 0.0567 (5) | |
O7 | 0.1916 (5) | 0.6117 (3) | 0.5624 (3) | 0.0704 (6) | |
O8 | 0.6324 (5) | 0.4954 (3) | 0.6468 (2) | 0.0698 (6) | |
H8A | 0.678 (8) | 0.498 (6) | 0.736 (3) | 0.092 (12)* | |
H8B | 0.582 (10) | 0.383 (3) | 0.596 (5) | 0.131 (19)* | |
H6A | 0.338 (9) | 0.632 (6) | 0.179 (5) | 0.091 (11)* | |
H7A | 0.344 (6) | 0.585 (7) | 0.583 (6) | 0.126 (18)* | |
H7B | 0.054 (7) | 0.527 (5) | 0.552 (6) | 0.14 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0340 (10) | 0.0373 (10) | 0.0301 (10) | 0.0034 (8) | 0.0027 (8) | 0.0153 (8) |
N3 | 0.0342 (8) | 0.0472 (10) | 0.0282 (8) | −0.0003 (7) | 0.0009 (6) | 0.0189 (7) |
C2 | 0.0308 (10) | 0.0388 (10) | 0.0270 (9) | 0.0037 (8) | 0.0015 (7) | 0.0129 (8) |
C3 | 0.0316 (9) | 0.0494 (12) | 0.0266 (9) | 0.0040 (8) | 0.0030 (7) | 0.0163 (8) |
C4 | 0.0329 (10) | 0.0427 (11) | 0.0276 (9) | 0.0065 (8) | 0.0035 (7) | 0.0173 (8) |
C5 | 0.0248 (9) | 0.0398 (10) | 0.0269 (9) | 0.0046 (7) | 0.0005 (7) | 0.0132 (8) |
C6 | 0.0287 (9) | 0.0423 (10) | 0.0244 (8) | 0.0061 (7) | −0.0014 (7) | 0.0132 (7) |
C10 | 0.0356 (11) | 0.0368 (10) | 0.0470 (12) | 0.0036 (9) | 0.0024 (9) | 0.0042 (9) |
C9 | 0.0408 (11) | 0.0467 (12) | 0.0405 (11) | 0.0051 (10) | 0.0121 (9) | 0.0198 (10) |
C8 | 0.0398 (11) | 0.0484 (12) | 0.0324 (10) | 0.0073 (9) | 0.0052 (8) | 0.0187 (9) |
C7 | 0.0330 (10) | 0.0389 (10) | 0.0424 (12) | 0.0066 (8) | 0.0061 (9) | 0.0169 (9) |
N1 | 0.0399 (10) | 0.0568 (11) | 0.0351 (9) | −0.0086 (8) | −0.0046 (8) | 0.0251 (9) |
N2 | 0.0392 (10) | 0.0636 (12) | 0.0297 (9) | −0.0101 (9) | −0.0037 (7) | 0.0245 (9) |
N4 | 0.0336 (9) | 0.0431 (9) | 0.0297 (8) | 0.0098 (7) | 0.0037 (7) | 0.0133 (7) |
O1 | 0.0370 (8) | 0.0581 (10) | 0.0569 (10) | 0.0120 (7) | 0.0113 (7) | 0.0367 (8) |
O2 | 0.0293 (7) | 0.0496 (8) | 0.0400 (8) | 0.0116 (6) | 0.0035 (6) | 0.0163 (7) |
O3 | 0.0402 (9) | 0.0705 (11) | 0.0483 (10) | −0.0027 (8) | 0.0037 (7) | 0.0362 (9) |
O4 | 0.0362 (8) | 0.0552 (10) | 0.0545 (10) | −0.0030 (7) | −0.0010 (7) | 0.0206 (8) |
O5 | 0.0399 (9) | 0.0578 (11) | 0.0701 (12) | −0.0085 (8) | 0.0015 (8) | 0.0102 (9) |
O6 | 0.0478 (10) | 0.0703 (11) | 0.0396 (9) | −0.0066 (8) | −0.0064 (7) | 0.0194 (8) |
O7 | 0.0750 (15) | 0.0552 (12) | 0.0817 (15) | 0.0054 (11) | −0.0010 (12) | 0.0371 (11) |
O8 | 0.0965 (17) | 0.0493 (11) | 0.0569 (12) | 0.0129 (11) | −0.0024 (12) | 0.0171 (10) |
C1—N2 | 1.324 (3) | C10—C9 | 1.485 (3) |
C1—N1 | 1.321 (3) | C9—C8 | 1.333 (3) |
C1—N3 | 1.330 (2) | C9—H9 | 0.9300 |
N3—C2 | 1.454 (3) | C8—C7 | 1.495 (3) |
N3—H3 | 0.8600 | C8—H8 | 0.9300 |
C2—C3 | 1.520 (3) | C7—O4 | 1.235 (3) |
C2—H2C | 0.9700 | C7—O3 | 1.269 (3) |
C2—H2D | 0.9700 | N1—H1A | 0.8600 |
C3—C4 | 1.521 (3) | N1—H1B | 0.8600 |
C3—H3B | 0.9700 | N2—H2A | 0.8600 |
C3—H3A | 0.9700 | N2—H2B | 0.8600 |
C4—C5 | 1.531 (3) | N4—H4AA | 0.8900 |
C4—H4B | 0.9700 | N4—H4BB | 0.8900 |
C4—H4A | 0.9700 | N4—H4CC | 0.8900 |
C5—N4 | 1.496 (3) | O3—H6A | 1.25 (5) |
C5—C6 | 1.531 (3) | O6—H6A | 1.15 (5) |
C5—H5 | 0.9800 | O7—H7A | 0.88 (2) |
C6—O1 | 1.235 (2) | O7—H7B | 0.86 (2) |
C6—O2 | 1.262 (2) | O8—H8A | 0.871 (19) |
C10—O5 | 1.222 (3) | O8—H8B | 0.87 (2) |
C10—O6 | 1.288 (3) | ||
N2—C1—N1 | 119.20 (18) | O1—C6—C5 | 118.50 (17) |
N2—C1—N3 | 120.33 (18) | O2—C6—C5 | 115.34 (17) |
N1—C1—N3 | 120.46 (18) | O5—C10—O6 | 120.3 (2) |
C1—N3—C2 | 122.46 (17) | O5—C10—C9 | 119.6 (2) |
C1—N3—H3 | 118.8 | O6—C10—C9 | 120.2 (2) |
C2—N3—H3 | 118.8 | C8—C9—C10 | 130.9 (2) |
N3—C2—C3 | 112.22 (16) | C8—C9—H9 | 114.6 |
N3—C2—H2C | 109.2 | C10—C9—H9 | 114.6 |
C3—C2—H2C | 109.2 | C9—C8—C7 | 130.1 (2) |
N3—C2—H2D | 109.2 | C9—C8—H8 | 114.9 |
C3—C2—H2D | 109.2 | C7—C8—H8 | 114.9 |
H2C—C2—H2D | 107.9 | O4—C7—O3 | 122.8 (2) |
C4—C3—C2 | 108.94 (15) | O4—C7—C8 | 117.7 (2) |
C4—C3—H3B | 109.9 | O3—C7—C8 | 119.47 (19) |
C2—C3—H3B | 109.9 | C1—N1—H1A | 120.0 |
C4—C3—H3A | 109.9 | C1—N1—H1B | 120.0 |
C2—C3—H3A | 109.9 | H1A—N1—H1B | 120.0 |
H3B—C3—H3A | 108.3 | C1—N2—H2A | 120.0 |
C3—C4—C5 | 116.33 (16) | C1—N2—H2B | 120.0 |
C3—C4—H4B | 108.2 | H2A—N2—H2B | 120.0 |
C5—C4—H4B | 108.2 | C5—N4—H4AA | 109.5 |
C3—C4—H4A | 108.2 | C5—N4—H4BB | 109.5 |
C5—C4—H4A | 108.2 | H4AA—N4—H4BB | 109.5 |
H4B—C4—H4A | 107.4 | C5—N4—H4CC | 109.5 |
N4—C5—C6 | 109.19 (15) | H4AA—N4—H4CC | 109.5 |
N4—C5—C4 | 111.67 (15) | H4BB—N4—H4CC | 109.5 |
C6—C5—C4 | 111.72 (16) | C7—O3—H6A | 111.2 (19) |
N4—C5—H5 | 108.0 | C10—O6—H6A | 109 (2) |
C6—C5—H5 | 108.0 | H7A—O7—H7B | 115 (5) |
C4—C5—H5 | 108.0 | H8A—O8—H8B | 106 (4) |
O1—C6—O2 | 126.16 (19) | ||
N2—C1—N3—C2 | 1.0 (3) | C4—C5—C6—O1 | 101.6 (2) |
N1—C1—N3—C2 | −179.8 (2) | N4—C5—C6—O2 | 158.32 (16) |
C1—N3—C2—C3 | −166.55 (19) | C4—C5—C6—O2 | −77.7 (2) |
N3—C2—C3—C4 | 168.85 (17) | O5—C10—C9—C8 | 179.8 (3) |
C2—C3—C4—C5 | 174.85 (18) | O6—C10—C9—C8 | 1.2 (4) |
C3—C4—C5—N4 | 57.3 (2) | C10—C9—C8—C7 | −0.4 (4) |
C3—C4—C5—C6 | −65.3 (2) | C9—C8—C7—O4 | 179.9 (2) |
N4—C5—C6—O1 | −22.4 (2) | C9—C8—C7—O3 | −1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4AA···O2i | 0.89 | 1.98 | 2.843 (2) | 162 |
N1—H1A···O1ii | 0.86 | 2.18 | 2.935 (2) | 147 |
N1—H1B···O3ii | 0.86 | 1.98 | 2.843 (2) | 176 |
N4—H4BB···O5iii | 0.89 | 2.23 | 3.079 (3) | 160 |
N2—H2A···O2ii | 0.86 | 2.10 | 2.948 (2) | 171 |
N2—H2B···O5iv | 0.86 | 2.08 | 2.862 (3) | 152 |
N3—H3···O4ii | 0.86 | 2.10 | 2.955 (2) | 172 |
N4—H4CC···O7v | 0.89 | 1.92 | 2.801 (2) | 173 |
O3—H6A···O6 | 1.28 (4) | 1.13 (4) | 2.407 (2) | 173 (3) |
O7—H7A···O8 | 0.90 (2) | 1.91 (2) | 2.791 (3) | 165 (5) |
O7—H7B···O1 | 0.87 (2) | 2.35 (4) | 3.081 (3) | 142 (5) |
O7—H7B···O8vi | 0.87 (2) | 2.57 (5) | 3.186 (4) | 129 (5) |
O8—H8A···O4ii | 0.87 (3) | 2.01 (2) | 2.873 (3) | 170 (4) |
O8—H8B···O2i | 0.88 (2) | 1.97 (3) | 2.770 (2) | 152 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1; (iii) x−1, y−1, z; (iv) x−1, y−1, z+1; (v) x, y−1, z; (vi) x−1, y, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register