Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004350/su6080sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004350/su6080Isup2.hkl |
CCDC reference: 238778
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.108
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT432_ALERT_2_C Short Inter X...Y Contact O15 .. C20 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Collect (Nonius, 1997–2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H14N2O8·2C3H7NO | Z = 1 |
Mr = 556.52 | F(000) = 292 |
Triclinic, P1 | Dx = 1.450 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.9519 (1) Å | Cell parameters from 11976 reflections |
b = 10.8758 (2) Å | θ = 3.1–28.3° |
c = 12.9078 (3) Å | µ = 0.11 mm−1 |
α = 111.985 (1)° | T = 123 K |
β = 95.578 (1)° | Plate, red |
γ = 94.095 (1)° | 0.26 × 0.12 × 0.05 mm |
V = 637.17 (2) Å3 |
Nonius KappaCCD diffractometer | 2266 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Horizonally mounted graphite crystal monochromator | θmax = 28.3°, θmin = 3.1° |
Detector resolution: 9 pixels mm-1 | h = −6→6 |
CCD scans | k = −14→14 |
11976 measured reflections | l = −17→17 |
3132 independent 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1167P] where P = (Fo2 + 2Fc2)/3 |
3132 reflections | (Δ/σ)max = 0.001 |
183 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.26 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 | 0.4386 (3) | 0.49628 (13) | 0.23584 (12) | 0.0214 (3) | |
C2 | 0.4498 (3) | 0.57134 (13) | 0.15918 (11) | 0.0202 (3) | |
H2A | 0.3526 | 0.5146 | 0.0836 | 0.024* | |
H2B | 0.6426 | 0.5923 | 0.1511 | 0.024* | |
C3 | 0.3198 (3) | 0.70013 (13) | 0.20541 (12) | 0.0206 (3) | |
H3A | 0.1200 | 0.6786 | 0.1999 | 0.025* | |
H3B | 0.3925 | 0.7486 | 0.2860 | 0.025* | |
N4 | 0.3746 (2) | 0.78706 (11) | 0.14326 (9) | 0.0187 (3) | |
C5 | 0.6107 (3) | 0.87750 (13) | 0.18261 (11) | 0.0180 (3) | |
C6 | 0.6592 (2) | 0.96879 (13) | 0.12316 (11) | 0.0169 (3) | |
C7 | 0.4761 (2) | 0.95622 (12) | 0.02825 (11) | 0.0150 (3) | |
C8 | 0.2454 (2) | 0.85935 (12) | −0.01183 (11) | 0.0163 (3) | |
C9 | 0.1893 (3) | 0.76971 (13) | 0.04845 (11) | 0.0190 (3) | |
O10 | −0.0095 (2) | 0.68612 (10) | 0.01956 (9) | 0.0281 (3) | |
C11 | 0.0698 (3) | 0.84859 (13) | −0.10511 (11) | 0.0191 (3) | |
H11 | −0.0844 | 0.7826 | −0.1317 | 0.023* | |
C12 | 0.8817 (3) | 1.06495 (13) | 0.16099 (11) | 0.0192 (3) | |
H12 | 1.0033 | 1.0729 | 0.2254 | 0.023* | |
O13 | 0.7657 (2) | 0.88150 (10) | 0.26362 (8) | 0.0258 (2) | |
O14 | 0.5612 (2) | 0.38693 (10) | 0.20171 (9) | 0.0295 (3) | |
H14 | 0.5486 | 0.3485 | 0.2469 | 0.035* | |
O15 | 0.3318 (3) | 0.53306 (12) | 0.32075 (10) | 0.0419 (3) | |
O16 | 0.4929 (2) | 0.25131 (10) | 0.33046 (9) | 0.0319 (3) | |
C17 | 0.3413 (3) | 0.29651 (14) | 0.40350 (12) | 0.0254 (3) | |
H17 | 0.2954 | 0.3843 | 0.4187 | 0.030* | |
N18 | 0.2389 (2) | 0.23137 (12) | 0.46183 (10) | 0.0243 (3) | |
C19 | 0.3013 (3) | 0.09786 (15) | 0.44595 (13) | 0.0314 (4) | |
H19A | 0.1389 | 0.0338 | 0.4078 | 0.047* | |
H19B | 0.3569 | 0.0938 | 0.5195 | 0.047* | |
H19C | 0.4503 | 0.0756 | 0.3998 | 0.047* | |
C20 | 0.0541 (3) | 0.29017 (18) | 0.54327 (14) | 0.0368 (4) | |
H20A | 0.0421 | 0.3829 | 0.5517 | 0.055* | |
H20B | 0.1234 | 0.2879 | 0.6162 | 0.055* | |
H20C | −0.1276 | 0.2393 | 0.5167 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0247 (7) | 0.0179 (7) | 0.0227 (8) | 0.0014 (6) | 0.0037 (6) | 0.0093 (6) |
C2 | 0.0243 (7) | 0.0185 (7) | 0.0189 (7) | 0.0004 (6) | 0.0036 (5) | 0.0086 (6) |
C3 | 0.0226 (7) | 0.0222 (7) | 0.0239 (7) | 0.0013 (6) | 0.0059 (5) | 0.0164 (6) |
N4 | 0.0205 (5) | 0.0191 (6) | 0.0216 (6) | 0.0019 (5) | 0.0054 (5) | 0.0129 (5) |
C5 | 0.0198 (6) | 0.0163 (6) | 0.0197 (7) | 0.0037 (5) | 0.0054 (5) | 0.0080 (5) |
C6 | 0.0187 (6) | 0.0158 (6) | 0.0179 (7) | 0.0043 (5) | 0.0058 (5) | 0.0073 (5) |
C7 | 0.0155 (6) | 0.0131 (6) | 0.0174 (7) | 0.0042 (5) | 0.0058 (5) | 0.0056 (5) |
C8 | 0.0172 (6) | 0.0140 (6) | 0.0193 (7) | 0.0029 (5) | 0.0050 (5) | 0.0073 (5) |
C9 | 0.0194 (6) | 0.0172 (6) | 0.0221 (7) | 0.0023 (5) | 0.0044 (5) | 0.0092 (6) |
O10 | 0.0269 (5) | 0.0258 (5) | 0.0348 (6) | −0.0074 (4) | −0.0008 (4) | 0.0183 (5) |
C11 | 0.0179 (6) | 0.0160 (6) | 0.0229 (7) | −0.0010 (5) | 0.0025 (5) | 0.0073 (5) |
C12 | 0.0203 (6) | 0.0190 (7) | 0.0179 (7) | 0.0018 (5) | 0.0005 (5) | 0.0071 (5) |
O13 | 0.0286 (5) | 0.0279 (5) | 0.0242 (6) | −0.0002 (4) | −0.0022 (4) | 0.0158 (4) |
O14 | 0.0439 (6) | 0.0240 (5) | 0.0304 (6) | 0.0139 (5) | 0.0149 (5) | 0.0171 (5) |
O15 | 0.0669 (8) | 0.0372 (7) | 0.0420 (7) | 0.0263 (6) | 0.0335 (6) | 0.0286 (6) |
O16 | 0.0443 (6) | 0.0316 (6) | 0.0304 (6) | 0.0144 (5) | 0.0154 (5) | 0.0195 (5) |
C17 | 0.0321 (8) | 0.0229 (7) | 0.0248 (8) | 0.0069 (6) | 0.0040 (6) | 0.0126 (6) |
N18 | 0.0259 (6) | 0.0265 (6) | 0.0241 (7) | 0.0037 (5) | 0.0035 (5) | 0.0138 (5) |
C19 | 0.0442 (9) | 0.0249 (8) | 0.0286 (9) | 0.0010 (7) | 0.0000 (7) | 0.0158 (7) |
C20 | 0.0311 (8) | 0.0518 (11) | 0.0362 (10) | 0.0120 (8) | 0.0124 (7) | 0.0236 (8) |
C1—O15 | 1.2065 (17) | C8—C9 | 1.4847 (18) |
C1—O14 | 1.3189 (16) | C9—O10 | 1.2175 (16) |
C1—C2 | 1.5025 (18) | C11—C12i | 1.4041 (18) |
C2—C3 | 1.5198 (18) | C11—H11 | 0.9500 |
C2—H2A | 0.9900 | C12—C11i | 1.4041 (18) |
C2—H2B | 0.9900 | C12—H12 | 0.9500 |
C3—N4 | 1.4779 (16) | O14—H14 | 0.8400 |
C3—H3A | 0.9900 | O16—C17 | 1.2400 (17) |
C3—H3B | 0.9900 | C17—N18 | 1.3221 (18) |
N4—C5 | 1.3924 (17) | C17—H17 | 0.9500 |
N4—C9 | 1.3997 (17) | N18—C19 | 1.4490 (18) |
C5—O13 | 1.2205 (16) | N18—C20 | 1.4556 (19) |
C5—C6 | 1.4847 (18) | C19—H19A | 0.9800 |
C6—C12 | 1.3764 (18) | C19—H19B | 0.9800 |
C6—C7 | 1.4079 (18) | C19—H19C | 0.9800 |
C7—C8 | 1.4098 (17) | C20—H20A | 0.9800 |
C7—C7i | 1.420 (2) | C20—H20B | 0.9800 |
C8—C11 | 1.3769 (18) | C20—H20C | 0.9800 |
O15—C1—O14 | 123.37 (13) | C7—C8—C9 | 119.53 (11) |
O15—C1—C2 | 123.53 (12) | O10—C9—N4 | 120.51 (12) |
O14—C1—C2 | 113.09 (11) | O10—C9—C8 | 122.69 (12) |
C1—C2—C3 | 111.07 (11) | N4—C9—C8 | 116.78 (11) |
C1—C2—H2A | 109.4 | C8—C11—C12i | 120.09 (12) |
C3—C2—H2A | 109.4 | C8—C11—H11 | 120.0 |
C1—C2—H2B | 109.4 | C12i—C11—H11 | 120.0 |
C3—C2—H2B | 109.4 | C6—C12—C11i | 120.48 (12) |
H2A—C2—H2B | 108.0 | C6—C12—H12 | 119.8 |
N4—C3—C2 | 111.71 (11) | C11i—C12—H12 | 119.8 |
N4—C3—H3A | 109.3 | C1—O14—H14 | 109.5 |
C2—C3—H3A | 109.3 | O16—C17—N18 | 124.78 (13) |
N4—C3—H3B | 109.3 | O16—C17—H17 | 117.6 |
C2—C3—H3B | 109.3 | N18—C17—H17 | 117.6 |
H3A—C3—H3B | 107.9 | C17—N18—C19 | 121.57 (12) |
C5—N4—C9 | 125.39 (11) | C17—N18—C20 | 121.19 (12) |
C5—N4—C3 | 117.02 (11) | C19—N18—C20 | 117.23 (12) |
C9—N4—C3 | 117.57 (11) | N18—C19—H19A | 109.5 |
O13—C5—N4 | 120.55 (12) | N18—C19—H19B | 109.5 |
O13—C5—C6 | 122.49 (12) | H19A—C19—H19B | 109.5 |
N4—C5—C6 | 116.94 (11) | N18—C19—H19C | 109.5 |
C12—C6—C7 | 120.47 (11) | H19A—C19—H19C | 109.5 |
C12—C6—C5 | 119.99 (12) | H19B—C19—H19C | 109.5 |
C7—C6—C5 | 119.54 (11) | N18—C20—H20A | 109.5 |
C6—C7—C8 | 121.69 (11) | N18—C20—H20B | 109.5 |
C6—C7—C7i | 119.23 (14) | H20A—C20—H20B | 109.5 |
C8—C7—C7i | 119.08 (15) | N18—C20—H20C | 109.5 |
C11—C8—C7 | 120.66 (11) | H20A—C20—H20C | 109.5 |
C11—C8—C9 | 119.80 (11) | H20B—C20—H20C | 109.5 |
Symmetry code: (i) −x+1, −y+2, −z. |
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