Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004423/tk6210sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004423/tk6210Isup2.hkl |
CCDC reference: 269876
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.080
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.780 0.940 Tmin' and Tmax expected: 0.926 0.943 RR' = 0.845 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - N2 .. 6.51 su
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 28.28 From the CIF: _reflns_number_total 2290 Count of symmetry unique reflns 2290 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 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C13H17N3O9 | F(000) = 752 |
Mr = 359.30 | Dx = 1.479 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8322 reflections |
a = 7.3201 (8) Å | θ = 2.6–30.5° |
b = 13.9189 (14) Å | µ = 0.13 mm−1 |
c = 15.8356 (16) Å | T = 100 K |
V = 1613.5 (3) Å3 | Block, colourless |
Z = 4 | 0.59 × 0.54 × 0.46 mm |
Bruker SMART APEX CCD diffractometer | 2290 independent reflections |
Radiation source: fine-focus sealed tube | 2267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003) | h = −9→9 |
Tmin = 0.780, Tmax = 0.940 | k = −18→18 |
16714 measured reflections | l = −21→21 |
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)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.080 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4038P] where P = (Fo2 + 2Fc2)/3 |
2290 reflections | (Δ/σ)max < 0.001 |
277 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.19 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 | −0.1831 (2) | 0.52204 (11) | 0.12761 (9) | 0.0150 (3) | |
H1 | −0.266 (3) | 0.5657 (15) | 0.0982 (13) | 0.018* | |
C2 | −0.0123 (2) | 0.57357 (11) | 0.15885 (9) | 0.0142 (3) | |
H2 | 0.055 (3) | 0.5299 (15) | 0.1930 (13) | 0.017* | |
C3 | 0.1042 (2) | 0.60849 (10) | 0.08515 (9) | 0.0140 (3) | |
H3 | 0.047 (3) | 0.6581 (15) | 0.0555 (13) | 0.017* | |
C4 | 0.1405 (2) | 0.52555 (10) | 0.02426 (9) | 0.0138 (3) | |
H4 | 0.211 (3) | 0.4742 (14) | 0.0503 (13) | 0.017* | |
C5 | −0.0447 (2) | 0.48387 (10) | −0.00201 (9) | 0.0138 (3) | |
H5 | −0.115 (3) | 0.5325 (15) | −0.0273 (13) | 0.017* | |
C6 | −0.0254 (2) | 0.40147 (11) | −0.06481 (10) | 0.0163 (3) | |
C7 | −0.0051 (2) | 0.66649 (11) | 0.28601 (10) | 0.0197 (3) | |
C8 | −0.0764 (3) | 0.75679 (14) | 0.32499 (11) | 0.0265 (4) | |
H8A | 0.013 (4) | 0.807 (2) | 0.3130 (17) | 0.040* | |
H8B | −0.193 (4) | 0.7742 (19) | 0.3023 (18) | 0.040* | |
H8C | −0.076 (4) | 0.7494 (18) | 0.3813 (19) | 0.040* | |
C9 | 0.3465 (2) | 0.72479 (11) | 0.09257 (10) | 0.0170 (3) | |
C10 | 0.5071 (3) | 0.75399 (13) | 0.14534 (12) | 0.0244 (3) | |
H10A | 0.497 (4) | 0.817 (2) | 0.1584 (16) | 0.037* | |
H10B | 0.525 (4) | 0.7140 (19) | 0.1899 (17) | 0.037* | |
H10C | 0.619 (4) | 0.7517 (18) | 0.1103 (17) | 0.037* | |
C11 | 0.4117 (2) | 0.55178 (12) | −0.05643 (10) | 0.0185 (3) | |
C12 | 0.4788 (3) | 0.59695 (13) | −0.13620 (11) | 0.0238 (3) | |
H12A | 0.592 (4) | 0.5687 (19) | −0.1493 (16) | 0.036* | |
H12B | 0.396 (4) | 0.5839 (18) | −0.1822 (15) | 0.036* | |
H12C | 0.481 (4) | 0.6646 (18) | −0.1242 (17) | 0.036* | |
C13 | 0.0860 (3) | 0.24400 (13) | −0.08288 (13) | 0.0297 (4) | |
H13A | 0.127 (4) | 0.260 (2) | −0.1366 (18) | 0.045* | |
H13B | 0.167 (4) | 0.201 (2) | −0.0541 (18) | 0.045* | |
H13C | −0.029 (4) | 0.213 (2) | −0.0889 (16) | 0.045* | |
N1 | −0.26772 (18) | 0.47678 (11) | 0.20086 (9) | 0.0190 (3) | |
N2 | −0.43604 (19) | 0.46702 (10) | 0.19694 (9) | 0.0179 (3) | |
N3 | −0.5866 (2) | 0.45280 (12) | 0.20316 (11) | 0.0277 (3) | |
O1 | −0.13118 (15) | 0.44639 (7) | 0.07185 (7) | 0.0151 (2) | |
O2 | −0.07091 (16) | 0.65637 (8) | 0.20579 (7) | 0.0172 (2) | |
O3 | 0.0996 (2) | 0.61158 (9) | 0.31791 (8) | 0.0304 (3) | |
O4 | 0.27176 (15) | 0.64265 (8) | 0.12274 (7) | 0.0167 (2) | |
O5 | 0.28953 (17) | 0.76741 (9) | 0.03207 (8) | 0.0244 (3) | |
O6 | 0.22653 (15) | 0.56054 (8) | −0.05105 (7) | 0.0157 (2) | |
O7 | 0.50254 (17) | 0.51504 (11) | −0.00226 (8) | 0.0279 (3) | |
O8 | −0.0864 (2) | 0.40298 (10) | −0.13485 (8) | 0.0293 (3) | |
O9 | 0.06567 (19) | 0.32880 (8) | −0.03045 (8) | 0.0234 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0155 (6) | 0.0145 (6) | 0.0151 (6) | −0.0003 (6) | 0.0005 (5) | 0.0002 (5) |
C2 | 0.0150 (6) | 0.0134 (6) | 0.0141 (6) | −0.0008 (6) | 0.0000 (5) | −0.0007 (5) |
C3 | 0.0136 (6) | 0.0133 (6) | 0.0150 (6) | −0.0011 (6) | −0.0013 (5) | 0.0001 (5) |
C4 | 0.0138 (6) | 0.0138 (6) | 0.0138 (6) | −0.0003 (5) | 0.0000 (5) | 0.0002 (5) |
C5 | 0.0137 (6) | 0.0140 (6) | 0.0137 (6) | −0.0002 (5) | −0.0007 (5) | 0.0002 (5) |
C6 | 0.0162 (7) | 0.0150 (6) | 0.0177 (6) | −0.0011 (6) | −0.0002 (6) | −0.0012 (5) |
C7 | 0.0248 (8) | 0.0190 (7) | 0.0154 (6) | −0.0059 (6) | 0.0004 (6) | −0.0028 (6) |
C8 | 0.0344 (9) | 0.0244 (8) | 0.0207 (8) | −0.0004 (8) | 0.0005 (7) | −0.0077 (6) |
C9 | 0.0165 (7) | 0.0146 (6) | 0.0199 (7) | −0.0016 (6) | 0.0034 (6) | −0.0027 (6) |
C10 | 0.0226 (8) | 0.0238 (8) | 0.0268 (8) | −0.0090 (7) | −0.0045 (7) | −0.0008 (7) |
C11 | 0.0148 (7) | 0.0214 (7) | 0.0192 (7) | −0.0025 (6) | 0.0015 (6) | −0.0052 (6) |
C12 | 0.0227 (8) | 0.0281 (8) | 0.0206 (7) | −0.0056 (7) | 0.0056 (7) | −0.0034 (7) |
C13 | 0.0395 (10) | 0.0188 (8) | 0.0310 (9) | 0.0082 (8) | −0.0012 (8) | −0.0093 (7) |
N1 | 0.0153 (6) | 0.0248 (6) | 0.0168 (6) | −0.0019 (5) | 0.0016 (5) | 0.0023 (5) |
N2 | 0.0204 (6) | 0.0156 (6) | 0.0176 (6) | −0.0004 (5) | 0.0013 (5) | 0.0016 (5) |
N3 | 0.0183 (7) | 0.0321 (8) | 0.0327 (8) | −0.0023 (6) | 0.0032 (6) | 0.0099 (7) |
O1 | 0.0171 (5) | 0.0135 (4) | 0.0149 (5) | −0.0017 (4) | 0.0017 (4) | −0.0009 (4) |
O2 | 0.0195 (5) | 0.0170 (5) | 0.0152 (5) | 0.0011 (4) | −0.0001 (5) | −0.0039 (4) |
O3 | 0.0444 (8) | 0.0240 (6) | 0.0230 (6) | 0.0016 (6) | −0.0131 (6) | −0.0023 (5) |
O4 | 0.0166 (5) | 0.0158 (5) | 0.0177 (5) | −0.0036 (4) | −0.0032 (4) | −0.0001 (4) |
O5 | 0.0240 (6) | 0.0221 (5) | 0.0272 (6) | −0.0053 (5) | −0.0011 (5) | 0.0059 (5) |
O6 | 0.0152 (5) | 0.0172 (5) | 0.0145 (5) | 0.0004 (4) | 0.0018 (4) | 0.0014 (4) |
O7 | 0.0166 (5) | 0.0445 (7) | 0.0224 (6) | 0.0021 (6) | −0.0018 (5) | 0.0012 (6) |
O8 | 0.0393 (7) | 0.0285 (6) | 0.0202 (6) | 0.0055 (6) | −0.0109 (6) | −0.0056 (5) |
O9 | 0.0331 (7) | 0.0171 (5) | 0.0201 (5) | 0.0072 (5) | −0.0041 (5) | −0.0040 (4) |
C1—O1 | 1.4258 (18) | C8—H8A | 0.97 (3) |
C1—N1 | 1.4582 (19) | C8—H8B | 0.96 (3) |
C1—C2 | 1.524 (2) | C8—H8C | 0.90 (3) |
C1—H1 | 0.98 (2) | C9—O5 | 1.201 (2) |
C2—O2 | 1.4370 (18) | C9—O4 | 1.3544 (18) |
C2—C3 | 1.525 (2) | C9—C10 | 1.499 (2) |
C2—H2 | 0.95 (2) | C10—H10A | 0.90 (3) |
C3—O4 | 1.4437 (17) | C10—H10B | 0.91 (3) |
C3—C4 | 1.527 (2) | C10—H10C | 0.99 (3) |
C3—H3 | 0.94 (2) | C11—O7 | 1.200 (2) |
C4—O6 | 1.4340 (17) | C11—O6 | 1.3637 (18) |
C4—C5 | 1.532 (2) | C11—C12 | 1.494 (2) |
C4—H4 | 0.97 (2) | C12—H12A | 0.94 (3) |
C5—O1 | 1.4287 (17) | C12—H12B | 0.96 (3) |
C5—C6 | 1.525 (2) | C12—H12C | 0.96 (3) |
C5—H5 | 0.94 (2) | C13—O9 | 1.451 (2) |
C6—O8 | 1.196 (2) | C13—H13A | 0.93 (3) |
C6—O9 | 1.3281 (19) | C13—H13B | 0.95 (3) |
C7—O3 | 1.194 (2) | C13—H13C | 0.95 (3) |
C7—O2 | 1.3661 (19) | N1—N2 | 1.2412 (19) |
C7—C8 | 1.495 (2) | N2—N3 | 1.124 (2) |
O1—C1—N1 | 106.66 (12) | C7—C8—H8B | 111.7 (16) |
O1—C1—C2 | 109.27 (12) | H8A—C8—H8B | 110 (2) |
N1—C1—C2 | 107.08 (12) | C7—C8—H8C | 108.3 (17) |
O1—C1—H1 | 109.3 (12) | H8A—C8—H8C | 106 (2) |
N1—C1—H1 | 112.7 (12) | H8B—C8—H8C | 114 (2) |
C2—C1—H1 | 111.7 (12) | O5—C9—O4 | 123.92 (15) |
O2—C2—C1 | 107.47 (12) | O5—C9—C10 | 125.66 (15) |
O2—C2—C3 | 107.90 (12) | O4—C9—C10 | 110.42 (14) |
C1—C2—C3 | 111.12 (12) | C9—C10—H10A | 109.1 (17) |
O2—C2—H2 | 111.9 (12) | C9—C10—H10B | 112.5 (17) |
C1—C2—H2 | 107.9 (12) | H10A—C10—H10B | 115 (2) |
C3—C2—H2 | 110.6 (12) | C9—C10—H10C | 109.2 (15) |
O4—C3—C2 | 105.33 (11) | H10A—C10—H10C | 103 (2) |
O4—C3—C4 | 111.20 (12) | H10B—C10—H10C | 107 (2) |
C2—C3—C4 | 109.85 (12) | O7—C11—O6 | 122.98 (15) |
O4—C3—H3 | 110.2 (12) | O7—C11—C12 | 126.99 (16) |
C2—C3—H3 | 111.6 (13) | O6—C11—C12 | 110.00 (14) |
C4—C3—H3 | 108.6 (13) | C11—C12—H12A | 107.5 (16) |
O6—C4—C3 | 110.16 (12) | C11—C12—H12B | 110.8 (15) |
O6—C4—C5 | 106.94 (11) | H12A—C12—H12B | 108 (2) |
C3—C4—C5 | 107.69 (11) | C11—C12—H12C | 104.5 (16) |
O6—C4—H4 | 111.7 (12) | H12A—C12—H12C | 116 (2) |
C3—C4—H4 | 112.3 (12) | H12B—C12—H12C | 110 (2) |
C5—C4—H4 | 107.8 (11) | O9—C13—H13A | 111.0 (18) |
O1—C5—C6 | 107.48 (11) | O9—C13—H13B | 107.1 (17) |
O1—C5—C4 | 107.95 (11) | H13A—C13—H13B | 113 (3) |
C6—C5—C4 | 112.35 (12) | O9—C13—H13C | 109.5 (17) |
O1—C5—H5 | 111.5 (13) | H13A—C13—H13C | 108 (2) |
C6—C5—H5 | 108.3 (12) | H13B—C13—H13C | 109 (2) |
C4—C5—H5 | 109.3 (12) | N2—N1—C1 | 115.43 (14) |
O8—C6—O9 | 125.51 (15) | N3—N2—N1 | 171.21 (18) |
O8—C6—C5 | 123.87 (14) | C1—O1—C5 | 110.82 (11) |
O9—C6—C5 | 110.61 (13) | C7—O2—C2 | 117.27 (12) |
O3—C7—O2 | 123.62 (15) | C9—O4—C3 | 118.39 (12) |
O3—C7—C8 | 126.00 (15) | C11—O6—C4 | 117.26 (12) |
O2—C7—C8 | 110.33 (14) | C6—O9—C13 | 115.89 (14) |
C7—C8—H8A | 106.4 (16) |
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