


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014027170/is5383sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989014027170/is5383Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014027170/is5383Isup3.cml |
CCDC reference: 1038820
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.081
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found Datablock: I
Alert level C PLAT352_ALERT_3_C Short N-H (X0.87,N1.01A) N1 - H1 ... 0.76 Ang. PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 Note PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ............... -0.0026 Check PLAT923_ALERT_1_C S values in the CIF and FCF Differ by ....... -0.032 Check
Alert level G PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.66 mm PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O1 .. C2 .. 2.92 Ang. PLAT791_ALERT_4_G The Model has Chirality at C3 ............. S Verify PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 2 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 4 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 3 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: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
C8H11NO5 | F(000) = 424 |
Mr = 201.18 | Dx = 1.401 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2 2ab | θ = 3.2–27.5° |
a = 7.9337 (19) Å | µ = 0.12 mm−1 |
b = 20.581 (5) Å | T = 293 K |
c = 5.8405 (14) Å | Prism, colorless |
V = 953.7 (4) Å3 | 0.66 × 0.39 × 0.14 mm |
Z = 4 |
Rigaku XtaLAB mini diffractometer | 2190 independent reflections |
Radiation source: fine-focus sealed tube | 2042 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 6.827 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | k = −26→26 |
Tmin = 0.926, Tmax = 0.984 | l = −7→7 |
9982 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0385P)2 + 0.167P] where P = (Fo2 + 2Fc2)/3 |
2190 reflections | (Δ/σ)max = 0.010 |
131 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 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 | ||
O1 | −0.02731 (16) | 0.77067 (6) | −0.0480 (2) | 0.0538 (4) | |
O2 | 0.10460 (14) | 0.72562 (4) | 0.25649 (18) | 0.0385 (3) | |
O3 | 0.27691 (18) | 0.70878 (5) | 0.5536 (2) | 0.0548 (4) | |
O4 | 0.19733 (14) | 0.94889 (5) | 0.93375 (19) | 0.0417 (3) | |
O5 | 0.26952 (18) | 1.03085 (5) | 0.7069 (2) | 0.0539 (4) | |
N1 | 0.15491 (17) | 0.82887 (6) | 0.1795 (2) | 0.0344 (3) | |
C1 | 0.06782 (19) | 0.77729 (7) | 0.1092 (3) | 0.0355 (3) | |
C2 | 0.22322 (19) | 0.74470 (6) | 0.4126 (3) | 0.0340 (3) | |
C3 | 0.26475 (17) | 0.81536 (6) | 0.3704 (2) | 0.0283 (3) | |
C4 | 0.23203 (19) | 0.85660 (6) | 0.5828 (3) | 0.0318 (3) | |
C5 | 0.2829 (3) | 0.92684 (7) | 0.5461 (3) | 0.0425 (4) | |
C6 | 0.24451 (18) | 0.96852 (6) | 0.7513 (3) | 0.0336 (3) | |
C7 | 0.2257 (3) | 1.07707 (7) | 0.8886 (4) | 0.0504 (5) | |
C8 | 0.3640 (3) | 1.08564 (9) | 1.0556 (4) | 0.0575 (5) | |
H1 | 0.156 (3) | 0.8596 (10) | 0.108 (4) | 0.0517* | |
H3 | 0.3827 | 0.8197 | 0.3231 | 0.0339* | |
H4A | 0.1132 | 0.8547 | 0.6210 | 0.0381* | |
H4B | 0.2950 | 0.8389 | 0.7108 | 0.0381* | |
H5A | 0.4027 | 0.9288 | 0.5139 | 0.0509* | |
H5B | 0.2234 | 0.9439 | 0.4140 | 0.0509* | |
H7A | 0.1261 | 1.0617 | 0.9682 | 0.0604* | |
H7B | 0.1990 | 1.1188 | 0.8204 | 0.0604* | |
H8A | 0.4623 | 1.1017 | 0.9782 | 0.0689* | |
H8B | 0.3895 | 1.0446 | 1.1259 | 0.0689* | |
H8C | 0.3301 | 1.1161 | 1.1711 | 0.0689* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0582 (7) | 0.0549 (7) | 0.0482 (7) | −0.0087 (6) | −0.0192 (6) | −0.0092 (6) |
O2 | 0.0425 (6) | 0.0261 (4) | 0.0470 (6) | −0.0067 (4) | −0.0017 (5) | −0.0028 (5) |
O3 | 0.0817 (9) | 0.0355 (5) | 0.0473 (6) | 0.0005 (6) | −0.0118 (7) | 0.0098 (5) |
O4 | 0.0598 (7) | 0.0274 (4) | 0.0380 (6) | −0.0052 (5) | 0.0094 (6) | −0.0030 (4) |
O5 | 0.0899 (9) | 0.0257 (5) | 0.0461 (6) | −0.0118 (6) | 0.0003 (7) | 0.0003 (5) |
N1 | 0.0486 (7) | 0.0267 (5) | 0.0280 (5) | −0.0060 (5) | −0.0048 (5) | 0.0024 (5) |
C1 | 0.0387 (7) | 0.0328 (7) | 0.0349 (7) | −0.0035 (6) | −0.0014 (6) | −0.0044 (6) |
C2 | 0.0431 (7) | 0.0275 (6) | 0.0313 (7) | −0.0004 (6) | 0.0049 (7) | −0.0027 (6) |
C3 | 0.0323 (6) | 0.0269 (6) | 0.0256 (6) | −0.0043 (5) | 0.0016 (5) | −0.0021 (5) |
C4 | 0.0411 (7) | 0.0278 (6) | 0.0264 (6) | −0.0037 (5) | 0.0040 (6) | −0.0032 (5) |
C5 | 0.0633 (10) | 0.0333 (7) | 0.0308 (7) | −0.0130 (7) | 0.0052 (8) | −0.0035 (6) |
C6 | 0.0402 (7) | 0.0245 (6) | 0.0361 (7) | −0.0054 (5) | −0.0046 (6) | 0.0002 (5) |
C7 | 0.0536 (9) | 0.0243 (6) | 0.0732 (11) | 0.0023 (7) | −0.0051 (9) | −0.0090 (7) |
C8 | 0.0606 (10) | 0.0450 (9) | 0.0668 (12) | 0.0006 (8) | −0.0007 (10) | −0.0164 (9) |
O1—C1 | 1.1964 (18) | C4—C5 | 1.5159 (18) |
O2—C2 | 1.3677 (18) | C4—H4A | 0.9700 |
O2—C1 | 1.3985 (18) | C4—H4B | 0.9700 |
O3—C2 | 1.1861 (17) | C5—C6 | 1.505 (2) |
O4—C6 | 1.1997 (18) | C5—H5A | 0.9700 |
O5—C6 | 1.3237 (15) | C5—H5B | 0.9700 |
O5—C7 | 1.467 (2) | C7—C8 | 1.478 (3) |
N1—C1 | 1.3314 (18) | C7—H7A | 0.9700 |
N1—C3 | 1.4423 (18) | C7—H7B | 0.9700 |
N1—H1 | 0.76 (2) | C8—H8A | 0.9600 |
C2—C3 | 1.5113 (17) | C8—H8B | 0.9600 |
C3—C4 | 1.5251 (17) | C8—H8C | 0.9600 |
C3—H3 | 0.9800 | ||
C2—O2—C1 | 109.58 (10) | H4A—C4—H4B | 107.9 |
C6—O5—C7 | 116.82 (14) | C6—C5—C4 | 112.17 (12) |
C1—N1—C3 | 113.46 (12) | C6—C5—H5A | 109.2 |
C1—N1—H1 | 119.9 (15) | C4—C5—H5A | 109.2 |
C3—N1—H1 | 125.7 (15) | C6—C5—H5B | 109.2 |
O1—C1—N1 | 130.91 (15) | C4—C5—H5B | 109.2 |
O1—C1—O2 | 121.12 (13) | H5A—C5—H5B | 107.9 |
N1—C1—O2 | 107.97 (12) | O4—C6—O5 | 123.17 (14) |
O3—C2—O2 | 122.09 (13) | O4—C6—C5 | 125.34 (12) |
O3—C2—C3 | 129.38 (14) | O5—C6—C5 | 111.49 (13) |
O2—C2—C3 | 108.53 (11) | O5—C7—C8 | 112.25 (14) |
N1—C3—C2 | 100.35 (11) | O5—C7—H7A | 109.2 |
N1—C3—C4 | 114.75 (11) | C8—C7—H7A | 109.2 |
C2—C3—C4 | 111.48 (11) | O5—C7—H7B | 109.2 |
N1—C3—H3 | 110.0 | C8—C7—H7B | 109.2 |
C2—C3—H3 | 110.0 | H7A—C7—H7B | 107.9 |
C4—C3—H3 | 110.0 | C7—C8—H8A | 109.5 |
C5—C4—C3 | 111.76 (11) | C7—C8—H8B | 109.5 |
C5—C4—H4A | 109.3 | H8A—C8—H8B | 109.5 |
C3—C4—H4A | 109.3 | C7—C8—H8C | 109.5 |
C5—C4—H4B | 109.3 | H8A—C8—H8C | 109.5 |
C3—C4—H4B | 109.3 | H8B—C8—H8C | 109.5 |
C3—N1—C1—O1 | −176.31 (16) | O3—C2—C3—C4 | −57.2 (2) |
C3—N1—C1—O2 | 3.49 (17) | O2—C2—C3—C4 | 122.05 (12) |
C2—O2—C1—O1 | 176.53 (14) | N1—C3—C4—C5 | −70.08 (16) |
C2—O2—C1—N1 | −3.30 (16) | C2—C3—C4—C5 | 176.72 (13) |
C1—O2—C2—O3 | −178.76 (14) | C3—C4—C5—C6 | 177.65 (13) |
C1—O2—C2—C3 | 1.89 (15) | C7—O5—C6—O4 | −4.1 (2) |
C1—N1—C3—C2 | −2.23 (15) | C7—O5—C6—C5 | 176.04 (14) |
C1—N1—C3—C4 | −121.83 (14) | C4—C5—C6—O4 | 8.0 (2) |
O3—C2—C3—N1 | −179.18 (16) | C4—C5—C6—O5 | −172.05 (13) |
O2—C2—C3—N1 | 0.11 (14) | C6—O5—C7—C8 | 84.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.76 (2) | 2.13 (2) | 2.8766 (17) | 170 (2) |
Symmetry code: (i) x, y, z−1. |