Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007556/sj2218sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007556/sj2218Isup2.hkl |
CCDC reference: 640492
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.027
- wR factor = 0.067
- Data-to-parameter ratio = 6.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.98
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N1 .. 5.11 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32
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 25.02 From the CIF: _reflns_number_total 1149 Count of symmetry unique reflns 1149 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C5H6N+·C8H4NO6− | F(000) = 600 |
Mr = 290.23 | Dx = 1.481 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 1799 reflections |
a = 14.607 (4) Å | θ = 2.8–26.4° |
b = 11.904 (4) Å | µ = 0.12 mm−1 |
c = 9.257 (3) Å | T = 294 K |
β = 126.051 (4)° | Block, colorless |
V = 1301.4 (7) Å3 | 0.24 × 0.20 × 0.16 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1149 independent reflections |
Radiation source: fine-focus sealed tube | 1053 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→17 |
Tmin = 0.974, Tmax = 0.982 | k = −11→14 |
3262 measured reflections | l = −10→10 |
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)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0378P)2 + 0.1688P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1149 reflections | Δρmax = 0.13 e Å−3 |
192 parameters | Δρmin = −0.13 e Å−3 |
2 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0075 (12) |
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 | ||
O1 | 0.34839 (15) | 0.68738 (15) | 0.4864 (2) | 0.0442 (5) | |
C1 | 0.37193 (18) | 0.7427 (2) | 0.6190 (3) | 0.0315 (6) | |
O2 | 0.34012 (16) | 0.84036 (16) | 0.6202 (2) | 0.0443 (5) | |
C2 | 0.45164 (18) | 0.6876 (2) | 0.8014 (3) | 0.0296 (5) | |
C3 | 0.5404 (2) | 0.7485 (2) | 0.9428 (3) | 0.0335 (6) | |
H3 | 0.5478 | 0.8244 | 0.9279 | 0.040* | |
C4 | 0.6186 (2) | 0.6975 (2) | 1.1068 (3) | 0.0354 (6) | |
H4 | 0.6774 | 0.7397 | 1.2003 | 0.043* | |
C5 | 0.60948 (19) | 0.5847 (2) | 1.1321 (3) | 0.0301 (5) | |
C8 | 0.6950 (2) | 0.5333 (2) | 1.3128 (3) | 0.0346 (6) | |
O3 | 0.75789 (19) | 0.59130 (17) | 1.4425 (3) | 0.0555 (6) | |
O4 | 0.69481 (16) | 0.42348 (15) | 1.3135 (2) | 0.0461 (5) | |
H3A | 0.7441 | 0.4007 | 1.4144 | 0.069* | |
C6 | 0.5216 (2) | 0.5209 (2) | 0.9931 (3) | 0.0316 (5) | |
H6 | 0.5146 | 0.4449 | 1.0081 | 0.038* | |
C7 | 0.44469 (18) | 0.57431 (19) | 0.8314 (3) | 0.0293 (5) | |
N1 | 0.34737 (18) | 0.50730 (19) | 0.6903 (3) | 0.0390 (6) | |
O5 | 0.25255 (14) | 0.54740 (17) | 0.6196 (3) | 0.0542 (6) | |
O6 | 0.36570 (19) | 0.41538 (19) | 0.6535 (3) | 0.0632 (6) | |
C9 | 0.0961 (2) | 0.5810 (2) | 0.1734 (3) | 0.0443 (7) | |
H9 | 0.1245 | 0.5468 | 0.2825 | 0.053* | |
N2 | 0.15243 (19) | 0.6659 (2) | 0.1667 (3) | 0.0448 (6) | |
H2 | 0.2144 | 0.6880 | 0.2638 | 0.054* | |
C10 | −0.0027 (2) | 0.5432 (3) | 0.0232 (4) | 0.0471 (7) | |
H10 | −0.0418 | 0.4835 | 0.0283 | 0.056* | |
C11 | −0.0431 (2) | 0.5958 (3) | −0.1368 (4) | 0.0519 (8) | |
H11 | −0.1104 | 0.5718 | −0.2413 | 0.062* | |
C12 | 0.0157 (3) | 0.6829 (3) | −0.1416 (4) | 0.0543 (8) | |
H12 | −0.0116 | 0.7186 | −0.2492 | 0.065* | |
C13 | 0.1157 (3) | 0.7180 (3) | 0.0136 (4) | 0.0525 (8) | |
H13 | 0.1569 | 0.7768 | 0.0117 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0435 (10) | 0.0466 (11) | 0.0265 (9) | 0.0029 (8) | 0.0118 (8) | 0.0056 (8) |
C1 | 0.0213 (11) | 0.0351 (14) | 0.0268 (12) | 0.0007 (10) | 0.0079 (10) | 0.0099 (11) |
O2 | 0.0441 (10) | 0.0401 (11) | 0.0315 (10) | 0.0143 (9) | 0.0128 (8) | 0.0146 (8) |
C2 | 0.0238 (11) | 0.0337 (14) | 0.0251 (11) | 0.0046 (9) | 0.0109 (10) | 0.0093 (9) |
C3 | 0.0327 (12) | 0.0274 (13) | 0.0304 (12) | 0.0018 (11) | 0.0131 (10) | 0.0069 (11) |
C4 | 0.0309 (12) | 0.0357 (14) | 0.0279 (12) | 0.0004 (10) | 0.0108 (11) | 0.0019 (10) |
C5 | 0.0273 (12) | 0.0331 (13) | 0.0228 (11) | 0.0076 (10) | 0.0109 (10) | 0.0072 (9) |
C8 | 0.0317 (12) | 0.0372 (15) | 0.0237 (12) | 0.0098 (11) | 0.0100 (11) | 0.0059 (11) |
O3 | 0.0590 (12) | 0.0432 (12) | 0.0273 (10) | 0.0122 (10) | 0.0047 (9) | 0.0041 (9) |
O4 | 0.0458 (11) | 0.0353 (11) | 0.0273 (9) | 0.0094 (8) | 0.0050 (9) | 0.0104 (8) |
C6 | 0.0290 (11) | 0.0290 (13) | 0.0288 (12) | 0.0045 (10) | 0.0126 (10) | 0.0082 (10) |
C7 | 0.0220 (11) | 0.0319 (13) | 0.0237 (12) | 0.0019 (9) | 0.0078 (10) | 0.0051 (10) |
N1 | 0.0336 (12) | 0.0396 (14) | 0.0274 (11) | −0.0067 (10) | 0.0088 (9) | 0.0075 (9) |
O5 | 0.0236 (9) | 0.0591 (13) | 0.0505 (12) | −0.0015 (9) | 0.0056 (8) | 0.0150 (10) |
O6 | 0.0606 (15) | 0.0457 (13) | 0.0562 (13) | −0.0067 (11) | 0.0194 (12) | −0.0132 (10) |
C9 | 0.0423 (16) | 0.0518 (18) | 0.0353 (15) | 0.0085 (13) | 0.0209 (14) | 0.0033 (13) |
N2 | 0.0371 (11) | 0.0456 (14) | 0.0367 (12) | −0.0008 (10) | 0.0134 (10) | −0.0123 (11) |
C10 | 0.0378 (15) | 0.0533 (18) | 0.0472 (16) | −0.0027 (12) | 0.0234 (13) | −0.0041 (13) |
C11 | 0.0355 (15) | 0.070 (2) | 0.0335 (15) | 0.0040 (15) | 0.0111 (12) | −0.0086 (14) |
C12 | 0.0611 (19) | 0.059 (2) | 0.0372 (15) | 0.0196 (17) | 0.0258 (14) | 0.0131 (13) |
C13 | 0.0602 (18) | 0.0405 (16) | 0.0571 (19) | 0.0036 (14) | 0.0347 (17) | 0.0001 (14) |
O1—C1 | 1.250 (3) | C7—N1 | 1.476 (3) |
C1—O2 | 1.255 (3) | N1—O6 | 1.222 (3) |
C1—C2 | 1.524 (3) | N1—O5 | 1.228 (3) |
C2—C3 | 1.387 (3) | C9—N2 | 1.328 (4) |
C2—C7 | 1.392 (3) | C9—C10 | 1.363 (4) |
C3—C4 | 1.391 (3) | C9—H9 | 0.9300 |
C3—H3 | 0.9300 | N2—C13 | 1.336 (4) |
C4—C5 | 1.383 (4) | N2—H2 | 0.8600 |
C4—H4 | 0.9300 | C10—C11 | 1.380 (5) |
C5—C6 | 1.391 (4) | C10—H10 | 0.9300 |
C5—C8 | 1.507 (3) | C11—C12 | 1.363 (4) |
C8—O3 | 1.210 (3) | C11—H11 | 0.9300 |
C8—O4 | 1.307 (3) | C12—C13 | 1.380 (4) |
O4—H3A | 0.8200 | C12—H12 | 0.9300 |
C6—C7 | 1.389 (3) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | ||
O1—C1—O2 | 127.4 (2) | C6—C7—N1 | 117.0 (2) |
O1—C1—C2 | 116.8 (2) | C2—C7—N1 | 119.50 (19) |
O2—C1—C2 | 115.8 (2) | O6—N1—O5 | 124.3 (2) |
C3—C2—C7 | 117.1 (2) | O6—N1—C7 | 118.4 (2) |
C3—C2—C1 | 120.1 (2) | O5—N1—C7 | 117.3 (2) |
C7—C2—C1 | 122.7 (2) | N2—C9—C10 | 121.1 (3) |
C2—C3—C4 | 120.9 (2) | N2—C9—H9 | 119.4 |
C2—C3—H3 | 119.6 | C10—C9—H9 | 119.4 |
C4—C3—H3 | 119.6 | C9—N2—C13 | 122.0 (2) |
C5—C4—C3 | 120.6 (2) | C9—N2—H2 | 119.0 |
C5—C4—H4 | 119.7 | C13—N2—H2 | 119.0 |
C3—C4—H4 | 119.7 | C9—C10—C11 | 118.2 (3) |
C4—C5—C6 | 120.1 (2) | C9—C10—H10 | 120.9 |
C4—C5—C8 | 118.9 (2) | C11—C10—H10 | 120.9 |
C6—C5—C8 | 121.0 (2) | C12—C11—C10 | 120.0 (3) |
O3—C8—O4 | 124.6 (2) | C12—C11—H11 | 120.0 |
O3—C8—C5 | 121.2 (2) | C10—C11—H11 | 120.0 |
O4—C8—C5 | 114.1 (2) | C11—C12—C13 | 119.9 (3) |
C8—O4—H3A | 109.5 | C11—C12—H12 | 120.1 |
C7—C6—C5 | 117.9 (2) | C13—C12—H12 | 120.1 |
C7—C6—H6 | 121.1 | N2—C13—C12 | 118.8 (3) |
C5—C6—H6 | 121.1 | N2—C13—H13 | 120.6 |
C6—C7—C2 | 123.4 (2) | C12—C13—H13 | 120.6 |
O1—C1—C2—C3 | 134.4 (2) | C5—C6—C7—N1 | −175.5 (2) |
O2—C1—C2—C3 | −43.5 (3) | C3—C2—C7—C6 | −0.3 (3) |
O1—C1—C2—C7 | −40.9 (3) | C1—C2—C7—C6 | 175.1 (2) |
O2—C1—C2—C7 | 141.1 (2) | C3—C2—C7—N1 | 175.5 (2) |
C7—C2—C3—C4 | 0.0 (3) | C1—C2—C7—N1 | −9.0 (3) |
C1—C2—C3—C4 | −175.6 (2) | C6—C7—N1—O6 | −50.7 (3) |
C2—C3—C4—C5 | 0.2 (4) | C2—C7—N1—O6 | 133.2 (3) |
C3—C4—C5—C6 | −0.1 (4) | C6—C7—N1—O5 | 128.0 (2) |
C3—C4—C5—C8 | −179.1 (2) | C2—C7—N1—O5 | −48.1 (3) |
C4—C5—C8—O3 | 13.2 (4) | C10—C9—N2—C13 | −0.2 (4) |
C6—C5—C8—O3 | −165.8 (3) | N2—C9—C10—C11 | −0.2 (4) |
C4—C5—C8—O4 | −165.9 (2) | C9—C10—C11—C12 | 0.2 (4) |
C6—C5—C8—O4 | 15.1 (4) | C10—C11—C12—C13 | 0.2 (5) |
C4—C5—C6—C7 | −0.2 (4) | C9—N2—C13—C12 | 0.6 (4) |
C8—C5—C6—C7 | 178.8 (2) | C11—C12—C13—N2 | −0.6 (4) |
C5—C6—C7—C2 | 0.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.82 | 2.655 (3) | 162 |
O4—H3A···O2i | 0.82 | 1.72 | 2.540 (2) | 174 |
Symmetry code: (i) x+1/2, y−1/2, z+1. |
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