Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003562/cf6155sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003562/cf6155Isup2.hkl |
CCDC reference: 183810
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.093
- Data-to-parameter ratio = 9.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.764 0.992 Tmin' and Tmax expected: 0.969 0.976 RR' = 0.775 Please check that your absorption correction is appropriate. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2217 Count of symmetry unique reflns 2232 Completeness (_total/calc) 99.33% 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 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2000) and SHELXL97.
C14H19NO10 | Dx = 1.430 Mg m−3 |
Mr = 361.30 | Melting point = 365–366 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5811 (2) Å | Cell parameters from 9393 reflections |
b = 16.9550 (6) Å | θ = 2.9–27.5° |
c = 17.7323 (6) Å | µ = 0.12 mm−1 |
V = 1677.96 (10) Å3 | T = 120 K |
Z = 4 | Block, colourless |
F(000) = 760 | 0.25 × 0.20 × 0.20 mm |
Nonius KappaCCD detector diffractometer | 2217 independent reflections |
Radiation source: fine-focus sealed tube | 1926 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
φ and ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | h = −7→7 |
Tmin = 0.764, Tmax = 0.992 | k = −19→21 |
10467 measured reflections | l = −22→22 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1398P] where P = (Fo2 + 2Fc2)/3 |
2217 reflections | (Δ/σ)max = 0.001 |
238 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 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 | ||
O5 | 0.0564 (3) | 1.04864 (8) | 0.14352 (8) | 0.0195 (3) | |
C1 | 0.1298 (4) | 0.98603 (12) | 0.19046 (11) | 0.0198 (4) | |
H1 | −0.0111 | 0.9664 | 0.2198 | 0.024* | |
O1 | 0.3096 (3) | 1.01304 (9) | 0.24170 (8) | 0.0220 (3) | |
C7 | 0.2257 (4) | 1.05514 (13) | 0.30218 (12) | 0.0245 (5) | |
O7 | 0.0160 (3) | 1.06349 (10) | 0.31475 (9) | 0.0323 (4) | |
C8 | 0.4264 (5) | 1.08823 (15) | 0.34718 (13) | 0.0324 (6) | |
H8A | 0.3804 | 1.0902 | 0.4005 | 0.049* | |
H8B | 0.4630 | 1.1416 | 0.3294 | 0.049* | |
H8C | 0.5683 | 1.0547 | 0.3413 | 0.049* | |
C2 | 0.2334 (4) | 0.91835 (12) | 0.14366 (11) | 0.0193 (4) | |
H2 | 0.0988 | 0.8900 | 0.1181 | 0.023* | |
O2 | 0.3600 (3) | 0.86324 (9) | 0.19146 (8) | 0.0238 (3) | |
C9 | 0.2227 (5) | 0.80986 (13) | 0.22860 (12) | 0.0255 (5) | |
O8 | 0.0088 (3) | 0.80580 (11) | 0.22082 (9) | 0.0351 (4) | |
C10 | 0.3728 (5) | 0.76043 (14) | 0.28026 (13) | 0.0355 (6) | |
H10A | 0.3062 | 0.7070 | 0.2829 | 0.053* | |
H10B | 0.3734 | 0.7839 | 0.3308 | 0.053* | |
H10C | 0.5372 | 0.7580 | 0.2610 | 0.053* | |
C3 | 0.4123 (4) | 0.94516 (12) | 0.08413 (11) | 0.0181 (4) | |
H3 | 0.5723 | 0.9555 | 0.1075 | 0.022* | |
O3 | 0.4277 (3) | 0.88084 (8) | 0.03011 (8) | 0.0200 (3) | |
C11 | 0.6455 (4) | 0.86169 (12) | 0.00183 (11) | 0.0200 (4) | |
O9 | 0.8293 (3) | 0.89291 (10) | 0.02056 (9) | 0.0291 (4) | |
C12 | 0.6241 (5) | 0.79711 (13) | −0.05536 (12) | 0.0268 (5) | |
H12A | 0.5521 | 0.7505 | −0.0318 | 0.040* | |
H12B | 0.7835 | 0.7837 | −0.0746 | 0.040* | |
H12C | 0.5225 | 0.8149 | −0.0971 | 0.040* | |
C4 | 0.3236 (4) | 1.01771 (11) | 0.04228 (11) | 0.0175 (4) | |
H4 | 0.1838 | 1.0037 | 0.0097 | 0.021* | |
O4 | 0.5189 (3) | 1.04521 (8) | −0.00333 (7) | 0.0183 (3) | |
C13 | 0.4614 (4) | 1.07868 (13) | −0.07107 (11) | 0.0192 (4) | |
O10 | 0.2600 (3) | 1.08249 (9) | −0.09427 (8) | 0.0251 (4) | |
C14 | 0.6795 (4) | 1.10887 (14) | −0.11025 (12) | 0.0248 (5) | |
H14A | 0.7023 | 1.1647 | −0.0979 | 0.037* | |
H14B | 0.6597 | 1.1030 | −0.1649 | 0.037* | |
H14C | 0.8198 | 1.0787 | −0.0937 | 0.037* | |
C5 | 0.2503 (4) | 1.08038 (12) | 0.10023 (11) | 0.0185 (4) | |
H5 | 0.3889 | 1.0909 | 0.1346 | 0.022* | |
C6 | 0.1751 (4) | 1.15714 (12) | 0.06316 (12) | 0.0202 (4) | |
N1 | −0.0594 (4) | 1.16937 (12) | 0.05512 (11) | 0.0240 (4) | |
H1A | −0.169 (5) | 1.1319 (17) | 0.0703 (16) | 0.041 (8)* | |
H1B | −0.116 (5) | 1.2086 (19) | 0.0295 (17) | 0.047 (8)* | |
O6 | 0.3343 (3) | 1.20229 (9) | 0.04220 (9) | 0.0271 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O5 | 0.0167 (7) | 0.0228 (7) | 0.0189 (6) | −0.0005 (6) | 0.0032 (6) | 0.0034 (6) |
C1 | 0.0177 (10) | 0.0224 (10) | 0.0192 (9) | −0.0009 (9) | −0.0006 (9) | 0.0024 (8) |
O1 | 0.0188 (8) | 0.0282 (7) | 0.0190 (7) | −0.0007 (7) | 0.0000 (6) | −0.0013 (6) |
C7 | 0.0256 (12) | 0.0269 (11) | 0.0210 (10) | 0.0011 (10) | 0.0017 (9) | −0.0006 (9) |
O7 | 0.0232 (9) | 0.0419 (10) | 0.0318 (8) | 0.0031 (8) | 0.0030 (8) | −0.0069 (7) |
C8 | 0.0309 (13) | 0.0391 (13) | 0.0271 (11) | −0.0080 (11) | −0.0010 (10) | −0.0056 (10) |
C2 | 0.0190 (10) | 0.0208 (10) | 0.0181 (9) | −0.0010 (8) | 0.0001 (8) | 0.0033 (8) |
O2 | 0.0249 (8) | 0.0235 (7) | 0.0231 (7) | 0.0009 (7) | 0.0003 (7) | 0.0071 (6) |
C9 | 0.0372 (14) | 0.0197 (11) | 0.0197 (10) | 0.0004 (10) | 0.0068 (10) | 0.0001 (8) |
O8 | 0.0335 (10) | 0.0362 (9) | 0.0356 (9) | −0.0068 (8) | 0.0083 (8) | 0.0078 (8) |
C10 | 0.0499 (16) | 0.0284 (12) | 0.0281 (11) | 0.0066 (12) | 0.0041 (13) | 0.0091 (10) |
C3 | 0.0182 (10) | 0.0181 (10) | 0.0178 (9) | −0.0002 (9) | 0.0003 (8) | −0.0025 (7) |
O3 | 0.0198 (7) | 0.0189 (7) | 0.0212 (7) | −0.0016 (6) | 0.0026 (6) | −0.0031 (6) |
C11 | 0.0196 (10) | 0.0223 (10) | 0.0181 (9) | 0.0050 (9) | 0.0012 (9) | 0.0037 (8) |
O9 | 0.0173 (8) | 0.0403 (9) | 0.0295 (8) | 0.0013 (7) | −0.0007 (7) | −0.0031 (7) |
C12 | 0.0308 (12) | 0.0243 (10) | 0.0252 (11) | 0.0036 (11) | 0.0023 (10) | −0.0014 (9) |
C4 | 0.0147 (10) | 0.0197 (9) | 0.0180 (9) | −0.0023 (8) | 0.0025 (8) | 0.0011 (8) |
O4 | 0.0145 (7) | 0.0224 (7) | 0.0179 (6) | −0.0021 (6) | 0.0013 (6) | 0.0032 (6) |
C13 | 0.0203 (11) | 0.0197 (10) | 0.0175 (9) | −0.0012 (9) | 0.0006 (9) | 0.0002 (8) |
O10 | 0.0181 (8) | 0.0342 (9) | 0.0230 (8) | −0.0009 (7) | −0.0035 (6) | 0.0059 (7) |
C14 | 0.0208 (11) | 0.0324 (11) | 0.0213 (10) | −0.0055 (10) | 0.0012 (9) | 0.0047 (9) |
C5 | 0.0163 (10) | 0.0212 (10) | 0.0179 (9) | −0.0022 (9) | 0.0023 (8) | 0.0006 (8) |
C6 | 0.0238 (11) | 0.0173 (10) | 0.0194 (9) | −0.0013 (9) | −0.0005 (9) | −0.0011 (8) |
N1 | 0.0227 (10) | 0.0213 (9) | 0.0279 (10) | 0.0022 (8) | −0.0002 (8) | 0.0056 (8) |
O6 | 0.0271 (9) | 0.0207 (7) | 0.0333 (8) | −0.0030 (7) | 0.0008 (7) | 0.0032 (7) |
O5—C1 | 1.410 (2) | C3—H3 | 1.000 |
O5—C5 | 1.432 (2) | O3—C11 | 1.355 (2) |
C1—O1 | 1.429 (2) | C11—O9 | 1.201 (3) |
C1—C2 | 1.530 (3) | C11—C12 | 1.497 (3) |
C1—H1 | 1.000 | C12—H12A | 0.980 |
O1—C7 | 1.371 (3) | C12—H12B | 0.980 |
C7—O7 | 1.200 (3) | C12—H12C | 0.980 |
C7—C8 | 1.485 (3) | C4—O4 | 1.435 (2) |
C8—H8A | 0.980 | C4—C5 | 1.534 (3) |
C8—H8B | 0.980 | C4—H4 | 1.000 |
C8—H8C | 0.980 | O4—C13 | 1.367 (2) |
C2—O2 | 1.446 (2) | C13—O10 | 1.198 (3) |
C2—C3 | 1.522 (3) | C13—C14 | 1.492 (3) |
C2—H2 | 1.000 | C14—H14A | 0.980 |
O2—C9 | 1.356 (3) | C14—H14B | 0.980 |
C9—O8 | 1.204 (3) | C14—H14C | 0.980 |
C9—C10 | 1.498 (3) | C5—C6 | 1.517 (3) |
C10—H10A | 0.980 | C5—H5 | 1.000 |
C10—H10B | 0.980 | C6—O6 | 1.231 (3) |
C10—H10C | 0.980 | C6—N1 | 1.332 (3) |
C3—O3 | 1.454 (2) | N1—H1A | 0.92 (3) |
C3—C4 | 1.519 (3) | N1—H1B | 0.87 (3) |
C1—O5—C5 | 112.31 (16) | C11—O3—C3 | 118.47 (16) |
O5—C1—O1 | 109.78 (15) | O9—C11—O3 | 123.95 (18) |
O5—C1—C2 | 110.76 (15) | O9—C11—C12 | 125.3 (2) |
O1—C1—C2 | 108.65 (17) | O3—C11—C12 | 110.74 (19) |
O5—C1—H1 | 109.2 | C11—C12—H12A | 109.5 |
O1—C1—H1 | 109.2 | C11—C12—H12B | 109.5 |
C2—C1—H1 | 109.2 | H12A—C12—H12B | 109.5 |
C7—O1—C1 | 115.11 (15) | C11—C12—H12C | 109.5 |
O7—C7—O1 | 122.7 (2) | H12A—C12—H12C | 109.5 |
O7—C7—C8 | 126.3 (2) | H12B—C12—H12C | 109.5 |
O1—C7—C8 | 111.06 (19) | O4—C4—C3 | 106.92 (16) |
C7—C8—H8A | 109.5 | O4—C4—C5 | 110.79 (15) |
C7—C8—H8B | 109.5 | C3—C4—C5 | 108.70 (15) |
H8A—C8—H8B | 109.5 | O4—C4—H4 | 110.1 |
C7—C8—H8C | 109.5 | C3—C4—H4 | 110.1 |
H8A—C8—H8C | 109.5 | C5—C4—H4 | 110.1 |
H8B—C8—H8C | 109.5 | C13—O4—C4 | 116.86 (16) |
O2—C2—C3 | 106.22 (17) | O10—C13—O4 | 122.98 (19) |
O2—C2—C1 | 110.57 (15) | O10—C13—C14 | 125.93 (18) |
C3—C2—C1 | 113.58 (17) | O4—C13—C14 | 111.09 (18) |
O2—C2—H2 | 108.8 | C13—C14—H14A | 109.5 |
C3—C2—H2 | 108.8 | C13—C14—H14B | 109.5 |
C1—C2—H2 | 108.8 | H14A—C14—H14B | 109.5 |
C9—O2—C2 | 116.10 (18) | C13—C14—H14C | 109.5 |
O8—C9—O2 | 122.9 (2) | H14A—C14—H14C | 109.5 |
O8—C9—C10 | 126.4 (2) | H14B—C14—H14C | 109.5 |
O2—C9—C10 | 110.7 (2) | O5—C5—C6 | 110.20 (17) |
C9—C10—H10A | 109.5 | O5—C5—C4 | 107.48 (15) |
C9—C10—H10B | 109.5 | C6—C5—C4 | 112.21 (16) |
H10A—C10—H10B | 109.5 | O5—C5—H5 | 109.0 |
C9—C10—H10C | 109.5 | C6—C5—H5 | 109.0 |
H10A—C10—H10C | 109.5 | C4—C5—H5 | 109.0 |
H10B—C10—H10C | 109.5 | O6—C6—N1 | 125.5 (2) |
O3—C3—C4 | 107.74 (15) | O6—C6—C5 | 117.67 (19) |
O3—C3—C2 | 105.76 (16) | N1—C6—C5 | 116.85 (19) |
C4—C3—C2 | 111.53 (17) | C6—N1—H1A | 120.9 (18) |
O3—C3—H3 | 110.6 | C6—N1—H1B | 122 (2) |
C4—C3—H3 | 110.6 | H1A—N1—H1B | 116 (3) |
C2—C3—H3 | 110.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O6i | 0.87 (3) | 1.99 (3) | 2.840 (3) | 165 (3) |
C2—H2···O9ii | 1.00 | 2.29 | 3.168 (3) | 146 |
C8—H8C···O7iii | 0.98 | 2.55 | 3.366 (3) | 141 |
C12—H12C···O7iv | 0.98 | 2.60 | 3.392 (3) | 138 |
C14—H14A···O6v | 0.98 | 2.57 | 3.529 (3) | 166 |
C14—H14C···O10iii | 0.98 | 2.46 | 3.283 (3) | 142 |
N1—H1A···O5 | 0.92 (3) | 2.29 (3) | 2.658 (2) | 103 (2) |
C3—H3···O9 | 1.00 | 2.36 | 2.734 (3) | 101 |
C4—H4···O10 | 1.00 | 2.32 | 2.682 (2) | 100 |
C5—H5···O1 | 1.00 | 2.36 | 2.776 (2) | 104 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1/2, −y+2, z−1/2; (v) x+1/2, −y+5/2, −z. |
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