Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401863X/cv6349sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680401863X/cv6349Isup2.hkl |
CCDC reference: 251638
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1996) and Materials Studio (Accelrys, 2001); software used to prepare material for publication: SHELXL97.
C6H10N3O2+·C4H5O6− | Z = 1 |
Mr = 305.25 | F(000) = 160 |
Triclinic, P1 | Dx = 1.602 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.3712 (18) Å | Cell parameters from 1902 reflections |
b = 7.637 (3) Å | θ = 2.6–28.1° |
c = 8.460 (3) Å | µ = 0.14 mm−1 |
α = 72.025 (5)° | T = 291 K |
β = 73.872 (5)° | Tabular, colourless |
γ = 81.144 (5)° | 0.5 × 0.3 × 0.1 mm |
V = 316.2 (2) Å3 |
Bruker SMART APEX CCD diffractometer | 1407 independent reflections |
Radiation source: fine-focus sealed tube | 1382 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
Thin–slice ω scans | θmax = 28.4°, θmin = 2.6° |
Absorption correction: multi-scan (Blessing, 1995) | h = −6→7 |
Tmin = 0.802, Tmax = 0.990 | k = −10→10 |
2658 measured reflections | l = −11→11 |
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)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.0492P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
1407 reflections | Δρmax = 0.20 e Å−3 |
194 parameters | Δρmin = −0.23 e Å−3 |
3 restraints | Absolute structure: Flack (1983), 999 friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.1 (10) |
Experimental. The data was collected at room temperature using a Bruker SMART– APEX CCD area-detector (Mo Kα radiation). Intensities were intergrated from a series of exposures. Each exposure covered 0.3° in ω, with an exposure time of 60 s and the total data set was more than a sphere. The SAINT software containing SADABS was used to intergrate and correct the data. |
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 | 0.3586 (4) | 0.6068 (3) | 0.9726 (3) | 0.0266 (4) | |
C2 | 0.1309 (4) | 0.5446 (3) | 1.0807 (3) | 0.0304 (4) | |
H2 | 0.0894 | 0.4222 | 1.1247 | 0.037* | |
C3 | 0.0985 (5) | 0.8457 (3) | 1.0290 (3) | 0.0345 (5) | |
H3 | 0.0345 | 0.9657 | 1.0301 | 0.041* | |
C4 | 0.6071 (4) | 0.5113 (3) | 0.8966 (3) | 0.0281 (4) | |
H4A | 0.6592 | 0.4110 | 0.9869 | 0.034* | |
H4B | 0.7413 | 0.5980 | 0.8512 | 0.034* | |
C5 | 0.5907 (4) | 0.4331 (3) | 0.7526 (3) | 0.0231 (4) | |
H5 | 0.4902 | 0.5219 | 0.6783 | 0.028* | |
C6 | 0.4623 (4) | 0.2491 (3) | 0.8279 (2) | 0.0250 (4) | |
C10 | 0.3127 (4) | −0.2293 (3) | 0.3859 (3) | 0.0251 (4) | |
C9 | 0.3823 (4) | −0.0281 (3) | 0.3345 (3) | 0.0242 (4) | |
H9 | 0.2383 | 0.0549 | 0.2972 | 0.029* | |
C8 | 0.4234 (4) | 0.0087 (3) | 0.4940 (2) | 0.0234 (4) | |
H8 | 0.2544 | 0.0091 | 0.5766 | 0.028* | |
C7 | 0.5222 (4) | 0.2003 (3) | 0.4405 (2) | 0.0242 (4) | |
N1 | −0.0266 (4) | 0.6956 (3) | 1.1129 (2) | 0.0315 (4) | |
H1 | −0.1819 | 0.6928 | 1.1774 | 0.038* | |
N2 | 0.3316 (4) | 0.7957 (3) | 0.9426 (2) | 0.0312 (4) | |
H2A | 0.4480 | 0.8700 | 0.8779 | 0.037* | |
N3 | 0.8606 (3) | 0.4022 (2) | 0.6513 (2) | 0.0266 (4) | |
H3A | 0.9285 | 0.5104 | 0.5969 | 0.040* | |
H3B | 0.8575 | 0.3448 | 0.5750 | 0.040* | |
H3C | 0.9570 | 0.3331 | 0.7214 | 0.040* | |
O1 | 0.6104 (3) | 0.1067 (2) | 0.8647 (2) | 0.0357 (4) | |
O2 | 0.2227 (3) | 0.2554 (3) | 0.8537 (3) | 0.0435 (4) | |
O7 | 0.0984 (3) | −0.2658 (2) | 0.4859 (2) | 0.0378 (4) | |
O8 | 0.4788 (3) | −0.3434 (2) | 0.3240 (2) | 0.0334 (3) | |
O5 | 0.6135 (3) | 0.0092 (2) | 0.20434 (19) | 0.0325 (4) | |
H500 | 0.5824 | 0.0285 | 0.1106 | 0.049* | |
O6 | 0.5920 (3) | −0.1283 (2) | 0.57310 (19) | 0.0312 (3) | |
H600 | 0.7422 | −0.1128 | 0.5170 | 0.047* | |
O3 | 0.3409 (3) | 0.3313 (2) | 0.4069 (2) | 0.0346 (4) | |
H300 | 0.3991 | 0.4321 | 0.3822 | 0.052* | |
O4 | 0.7451 (3) | 0.2238 (2) | 0.4303 (2) | 0.0368 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0303 (10) | 0.0253 (9) | 0.0254 (9) | −0.0044 (8) | −0.0058 (8) | −0.0086 (7) |
C2 | 0.0305 (11) | 0.0274 (11) | 0.0330 (10) | −0.0071 (8) | −0.0041 (9) | −0.0088 (8) |
C3 | 0.0353 (11) | 0.0256 (10) | 0.0388 (11) | −0.0048 (9) | −0.0002 (9) | −0.0101 (9) |
C4 | 0.0256 (9) | 0.0298 (10) | 0.0319 (10) | −0.0049 (8) | −0.0057 (8) | −0.0128 (8) |
C5 | 0.0215 (9) | 0.0208 (9) | 0.0257 (9) | −0.0019 (7) | −0.0047 (7) | −0.0055 (7) |
C6 | 0.0264 (10) | 0.0258 (10) | 0.0230 (8) | −0.0095 (7) | −0.0046 (7) | −0.0046 (7) |
C10 | 0.0286 (10) | 0.0177 (9) | 0.0300 (10) | −0.0047 (7) | −0.0064 (8) | −0.0071 (7) |
C9 | 0.0275 (9) | 0.0159 (8) | 0.0280 (9) | −0.0043 (7) | −0.0036 (8) | −0.0058 (7) |
C8 | 0.0220 (9) | 0.0194 (9) | 0.0261 (9) | −0.0037 (7) | 0.0005 (7) | −0.0070 (7) |
C7 | 0.0283 (9) | 0.0213 (9) | 0.0234 (9) | −0.0051 (7) | −0.0011 (7) | −0.0098 (7) |
N1 | 0.0284 (9) | 0.0318 (9) | 0.0311 (9) | −0.0069 (7) | 0.0020 (7) | −0.0102 (7) |
N2 | 0.0315 (9) | 0.0265 (9) | 0.0307 (8) | −0.0084 (7) | 0.0018 (7) | −0.0068 (7) |
N3 | 0.0248 (8) | 0.0240 (8) | 0.0291 (9) | −0.0078 (6) | −0.0001 (7) | −0.0078 (7) |
O1 | 0.0322 (8) | 0.0230 (7) | 0.0456 (9) | −0.0066 (6) | −0.0066 (7) | −0.0012 (6) |
O2 | 0.0268 (9) | 0.0372 (9) | 0.0622 (12) | −0.0109 (7) | −0.0113 (8) | −0.0035 (8) |
O7 | 0.0277 (8) | 0.0237 (8) | 0.0544 (10) | −0.0079 (6) | 0.0058 (7) | −0.0114 (7) |
O8 | 0.0335 (8) | 0.0197 (7) | 0.0435 (9) | −0.0076 (6) | 0.0041 (7) | −0.0133 (6) |
O5 | 0.0410 (9) | 0.0289 (8) | 0.0242 (7) | −0.0127 (7) | 0.0021 (6) | −0.0068 (6) |
O6 | 0.0315 (8) | 0.0260 (7) | 0.0302 (7) | −0.0017 (6) | −0.0049 (6) | −0.0018 (6) |
O3 | 0.0304 (8) | 0.0177 (7) | 0.0535 (10) | −0.0056 (5) | −0.0057 (7) | −0.0091 (6) |
O4 | 0.0297 (8) | 0.0351 (8) | 0.0491 (9) | −0.0086 (6) | −0.0085 (7) | −0.0150 (7) |
C1—C2 | 1.359 (3) | C10—C9 | 1.538 (3) |
C1—N2 | 1.377 (3) | C9—O5 | 1.411 (3) |
C1—C4 | 1.497 (3) | C9—C8 | 1.539 (3) |
C2—N1 | 1.373 (3) | C9—H9 | 0.9800 |
C2—H2 | 0.9300 | C8—O6 | 1.406 (2) |
C3—N1 | 1.319 (3) | C8—C7 | 1.525 (3) |
C3—N2 | 1.328 (3) | C8—H8 | 0.9800 |
C3—H3 | 0.9300 | C7—O4 | 1.213 (3) |
C4—C5 | 1.540 (3) | C7—O3 | 1.307 (3) |
C4—H4A | 0.9700 | N1—H1 | 0.8600 |
C4—H4B | 0.9700 | N2—H2A | 0.8600 |
C5—N3 | 1.490 (3) | N3—H3A | 0.8900 |
C5—C6 | 1.536 (3) | N3—H3B | 0.8900 |
C5—H5 | 0.9800 | N3—H3C | 0.8900 |
C6—O2 | 1.240 (3) | O5—H500 | 0.8200 |
C6—O1 | 1.255 (3) | O6—H600 | 0.8200 |
C10—O7 | 1.237 (3) | O3—H300 | 0.8200 |
C10—O8 | 1.269 (3) | ||
C2—C1—N2 | 105.75 (18) | C10—C9—C8 | 107.52 (16) |
C2—C1—C4 | 133.0 (2) | O5—C9—H9 | 109.5 |
N2—C1—C4 | 121.18 (19) | C10—C9—H9 | 109.5 |
C1—C2—N1 | 107.40 (19) | C8—C9—H9 | 109.5 |
C1—C2—H2 | 126.3 | O6—C8—C7 | 111.96 (16) |
N1—C2—H2 | 126.3 | O6—C8—C9 | 112.15 (15) |
N1—C3—N2 | 108.2 (2) | C7—C8—C9 | 108.21 (15) |
N1—C3—H3 | 125.9 | O6—C8—H8 | 108.1 |
N2—C3—H3 | 125.9 | C7—C8—H8 | 108.1 |
C1—C4—C5 | 114.23 (17) | C9—C8—H8 | 108.1 |
C1—C4—H4A | 108.7 | O4—C7—O3 | 125.39 (19) |
C5—C4—H4A | 108.7 | O4—C7—C8 | 122.49 (19) |
C1—C4—H4B | 108.7 | O3—C7—C8 | 112.12 (17) |
C5—C4—H4B | 108.7 | C3—N1—C2 | 109.1 (2) |
H4A—C4—H4B | 107.6 | C3—N1—H1 | 125.5 |
N3—C5—C6 | 109.32 (16) | C2—N1—H1 | 125.5 |
N3—C5—C4 | 107.87 (16) | C3—N2—C1 | 109.61 (18) |
C6—C5—C4 | 110.70 (17) | C3—N2—H2A | 125.2 |
N3—C5—H5 | 109.6 | C1—N2—H2A | 125.2 |
C6—C5—H5 | 109.6 | C5—N3—H3A | 109.5 |
C4—C5—H5 | 109.6 | C5—N3—H3B | 109.5 |
O2—C6—O1 | 126.2 (2) | H3A—N3—H3B | 109.5 |
O2—C6—C5 | 117.46 (19) | C5—N3—H3C | 109.5 |
O1—C6—C5 | 116.27 (17) | H3A—N3—H3C | 109.5 |
O7—C10—O8 | 125.67 (19) | H3B—N3—H3C | 109.5 |
O7—C10—C9 | 116.51 (18) | C9—O5—H500 | 109.5 |
O8—C10—C9 | 117.82 (18) | C8—O6—H600 | 109.5 |
O5—C9—C10 | 113.51 (16) | C7—O3—H300 | 109.5 |
O5—C9—C8 | 107.33 (16) | ||
N2—C1—C2—N1 | 0.1 (2) | O5—C9—C8—O6 | −72.73 (19) |
C4—C1—C2—N1 | 177.5 (2) | C10—C9—C8—O6 | 49.7 (2) |
C2—C1—C4—C5 | 74.0 (3) | O5—C9—C8—C7 | 51.25 (19) |
N2—C1—C4—C5 | −108.9 (2) | C10—C9—C8—C7 | 173.71 (16) |
C1—C4—C5—N3 | 160.87 (17) | O6—C8—C7—O4 | 16.5 (3) |
C1—C4—C5—C6 | −79.6 (2) | C9—C8—C7—O4 | −107.6 (2) |
N3—C5—C6—O2 | −151.42 (19) | O6—C8—C7—O3 | −164.12 (16) |
C4—C5—C6—O2 | 89.9 (2) | C9—C8—C7—O3 | 71.8 (2) |
N3—C5—C6—O1 | 31.7 (2) | N2—C3—N1—C2 | 0.4 (3) |
C4—C5—C6—O1 | −87.0 (2) | C1—C2—N1—C3 | −0.3 (3) |
O7—C10—C9—O5 | −172.49 (18) | N1—C3—N2—C1 | −0.4 (3) |
O8—C10—C9—O5 | 8.1 (3) | C2—C1—N2—C3 | 0.2 (2) |
O7—C10—C9—C8 | 69.0 (2) | C4—C1—N2—C3 | −177.6 (2) |
O8—C10—C9—C8 | −110.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O8i | 0.86 | 1.90 | 2.760 (2) | 173 |
N1—H1···O5i | 0.86 | 2.55 | 2.993 (3) | 113 |
N2—H2A···O1ii | 0.86 | 2.09 | 2.810 (3) | 142 |
N2—H2A···O6ii | 0.86 | 2.47 | 2.961 (3) | 117 |
N3—H3A···O7iii | 0.89 | 1.91 | 2.799 (2) | 176 |
N3—H3C···O2iv | 0.89 | 1.96 | 2.822 (3) | 162 |
O5—H500···O1v | 0.82 | 1.95 | 2.741 (3) | 163 |
O6—H600···O7iv | 0.82 | 2.08 | 2.744 (2) | 138 |
O3—H300···O8ii | 0.82 | 1.72 | 2.533 (2) | 172 |
Symmetry codes: (i) x−1, y+1, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y, z; (v) x, y, z−1. |