Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021551/bv2056sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021551/bv2056Isup2.hkl |
CCDC reference: 651418
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- H-atom completeness 91%
- Disorder in main residue
- R factor = 0.064
- wR factor = 0.158
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O51 .. 2.73 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O51 .. 2.73 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT395_ALERT_2_C Deviating X-O-Y Angle from 120 Deg for <O51 150.40 Deg. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O52 .. 2.86 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O52 .. 2.86 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 12.60 Deg. O4 -C8 -BR1 1.555 1.555 1.555
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22.84 H28.18 Br0.16 O8.17 Atom count from the _atom_site data: C22.83799 H25.51399 Br0.162 O8 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C22.84 H28.18 Br0.16 O8.17 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 91.36 91.35 0.01 H 112.72 102.06 10.66 Br 0.64 0.65 -0.01 O 32.68 32.63 0.05
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
0.919C23H26O7·0.081C21H20Br2O5·1.333H2O | F(000) = 945 |
Mr = 446.26 | Dx = 1.394 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2202 reflections |
a = 34.035 (3) Å | θ = 2.9–27.5° |
b = 8.4017 (9) Å | µ = 0.40 mm−1 |
c = 7.4385 (5) Å | T = 120 K |
β = 90.305 (6)° | Rod, yellow |
V = 2127.0 (3) Å3 | 0.44 × 0.16 × 0.04 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2346 independent reflections |
Radiation source: fine-focus sealed tube | 1278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ω and φ scans | θmax = 27.5°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −44→43 |
Tmin = 0.842, Tmax = 0.984 | k = −10→7 |
8542 measured reflections | l = −8→9 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.7883P] where P = (Fo2 + 2Fc2)/3 |
2346 reflections | (Δ/σ)max < 0.001 |
153 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.32 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 | Occ. (<1) | |
C1 | 0.5000 | 0.4937 (5) | 0.2500 | 0.0279 (9) | |
C2 | 0.53215 (7) | 0.5859 (3) | 0.3301 (3) | 0.0293 (6) | |
H2 | 0.5293 | 0.6983 | 0.3371 | 0.035* | |
C3 | 0.56507 (7) | 0.5209 (3) | 0.3934 (3) | 0.0279 (6) | |
H3 | 0.5674 | 0.4086 | 0.3829 | 0.033* | |
C4 | 0.59804 (7) | 0.6052 (3) | 0.4776 (3) | 0.0255 (6) | |
C5 | 0.63270 (7) | 0.5226 (3) | 0.5148 (3) | 0.0253 (6) | |
H5 | 0.6343 | 0.4124 | 0.4872 | 0.030* | |
C6 | 0.66480 (7) | 0.5986 (3) | 0.5912 (3) | 0.0250 (6) | |
C7 | 0.66279 (8) | 0.7617 (3) | 0.6267 (3) | 0.0278 (6) | |
C8 | 0.62785 (8) | 0.8441 (3) | 0.5931 (3) | 0.0276 (6) | |
C9 | 0.59558 (8) | 0.7673 (3) | 0.5210 (3) | 0.0274 (6) | |
H9 | 0.5718 | 0.8239 | 0.5008 | 0.033* | |
C10 | 0.70173 (8) | 0.3620 (3) | 0.6116 (3) | 0.0334 (7) | |
H10A | 0.7276 | 0.3238 | 0.6509 | 0.050* | |
H10B | 0.6979 | 0.3367 | 0.4841 | 0.050* | |
H10C | 0.6812 | 0.3099 | 0.6826 | 0.050* | |
C11 | 0.71550 (8) | 0.9345 (3) | 0.5737 (4) | 0.0354 (7) | |
H11A | 0.7353 | 0.9988 | 0.6367 | 0.053* | |
H11B | 0.6970 | 1.0049 | 0.5111 | 0.053* | |
H11C | 0.7285 | 0.8653 | 0.4862 | 0.053* | |
C12 | 0.59576 (13) | 1.0940 (4) | 0.5921 (4) | 0.0346 (8) | 0.919 (3) |
H12A | 0.5997 | 1.2051 | 0.6284 | 0.052* | 0.919 (3) |
H12B | 0.5724 | 1.0515 | 0.6520 | 0.052* | 0.919 (3) |
H12C | 0.5921 | 1.0886 | 0.4615 | 0.052* | 0.919 (3) |
O1 | 0.5000 | 0.3467 (3) | 0.2500 | 0.0358 (7) | |
O2 | 0.69958 (5) | 0.5252 (2) | 0.6358 (2) | 0.0317 (5) | |
O3 | 0.69468 (5) | 0.8390 (2) | 0.7011 (2) | 0.0328 (5) | |
O4 | 0.62902 (9) | 1.0031 (4) | 0.6420 (3) | 0.0366 (7) | 0.919 (3) |
Br1 | 0.61971 (18) | 1.0626 (7) | 0.6264 (7) | 0.0286 (17)* | 0.081 (3) |
O51 | 0.4922 (2) | 0.0285 (8) | 0.1864 (9) | 0.0604 (19)* | 0.33 |
O52 | 0.4914 (2) | 0.0493 (9) | 0.0659 (11) | 0.076 (2)* | 0.33 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.030 (2) | 0.030 (2) | 0.0236 (18) | 0.000 | 0.0019 (15) | 0.000 |
C2 | 0.0308 (15) | 0.0243 (14) | 0.0327 (14) | 0.0010 (13) | 0.0019 (11) | 0.0012 (11) |
C3 | 0.0320 (16) | 0.0263 (15) | 0.0253 (13) | −0.0012 (12) | 0.0019 (11) | 0.0011 (11) |
C4 | 0.0277 (14) | 0.0263 (15) | 0.0226 (12) | −0.0005 (12) | 0.0009 (10) | 0.0003 (10) |
C5 | 0.0315 (15) | 0.0197 (13) | 0.0247 (13) | −0.0010 (12) | 0.0017 (11) | −0.0006 (10) |
C6 | 0.0270 (15) | 0.0271 (15) | 0.0209 (12) | −0.0018 (12) | 0.0017 (10) | 0.0005 (10) |
C7 | 0.0329 (15) | 0.0268 (15) | 0.0238 (13) | −0.0057 (12) | −0.0024 (11) | 0.0007 (11) |
C8 | 0.0371 (17) | 0.0211 (15) | 0.0245 (13) | −0.0035 (12) | 0.0015 (11) | −0.0003 (10) |
C9 | 0.0310 (15) | 0.0239 (14) | 0.0272 (13) | 0.0034 (12) | 0.0019 (11) | 0.0011 (11) |
C10 | 0.0324 (17) | 0.0368 (17) | 0.0308 (14) | 0.0054 (13) | −0.0050 (11) | −0.0009 (12) |
C11 | 0.0352 (16) | 0.0328 (17) | 0.0384 (15) | −0.0078 (13) | −0.0009 (12) | 0.0084 (12) |
C12 | 0.049 (3) | 0.0247 (17) | 0.0306 (17) | 0.0035 (17) | −0.0008 (16) | −0.0013 (13) |
O1 | 0.0354 (16) | 0.0317 (17) | 0.0403 (15) | 0.000 | −0.0017 (12) | 0.000 |
O2 | 0.0261 (11) | 0.0349 (11) | 0.0340 (10) | −0.0006 (9) | −0.0042 (8) | 0.0001 (8) |
O3 | 0.0382 (11) | 0.0305 (11) | 0.0298 (9) | −0.0086 (9) | −0.0052 (8) | 0.0034 (8) |
O4 | 0.0403 (17) | 0.0331 (16) | 0.0365 (14) | 0.0034 (14) | −0.0066 (10) | −0.0019 (11) |
C1—O1 | 1.235 (4) | C8—Br1 | 1.873 (6) |
C1—C2 | 1.465 (3) | C9—H9 | 0.9500 |
C1—C2i | 1.465 (3) | C10—O2 | 1.385 (3) |
C2—C3 | 1.330 (3) | C10—H10A | 0.9800 |
C2—H2 | 0.9500 | C10—H10B | 0.9800 |
C3—C4 | 1.465 (3) | C10—H10C | 0.9800 |
C3—H3 | 0.9500 | C11—O3 | 1.432 (3) |
C4—C5 | 1.395 (3) | C11—H11A | 0.9800 |
C4—C9 | 1.402 (3) | C11—H11B | 0.9800 |
C5—C6 | 1.385 (3) | C11—H11C | 0.9800 |
C5—H5 | 0.9500 | C12—O4 | 1.414 (6) |
C6—O2 | 1.374 (3) | C12—H12A | 0.9800 |
C6—C7 | 1.397 (3) | C12—H12B | 0.9800 |
C7—O3 | 1.379 (3) | C12—H12C | 0.9800 |
C7—C8 | 1.398 (3) | O51—O52 | 0.914 (8) |
C8—C9 | 1.380 (3) | O51—O51i | 1.084 (12) |
C8—O4 | 1.385 (4) | O52—O52ii | 1.411 (15) |
O1—C1—C2 | 121.94 (17) | C9—C8—Br1 | 113.1 (3) |
O1—C1—C2i | 121.94 (17) | O4—C8—Br1 | 12.6 (2) |
C2—C1—C2i | 116.1 (3) | C7—C8—Br1 | 126.0 (3) |
C3—C2—C1 | 123.5 (3) | C8—C9—C4 | 119.7 (2) |
C3—C2—H2 | 118.2 | C8—C9—H9 | 120.2 |
C1—C2—H2 | 118.2 | C4—C9—H9 | 120.2 |
C2—C3—C4 | 126.5 (3) | O2—C10—H10A | 109.5 |
C2—C3—H3 | 116.8 | O2—C10—H10B | 109.5 |
C4—C3—H3 | 116.8 | H10A—C10—H10B | 109.5 |
C5—C4—C9 | 119.3 (2) | O2—C10—H10C | 109.5 |
C5—C4—C3 | 119.3 (2) | H10A—C10—H10C | 109.5 |
C9—C4—C3 | 121.4 (2) | H10B—C10—H10C | 109.5 |
C6—C5—C4 | 121.1 (2) | O3—C11—H11A | 109.5 |
C6—C5—H5 | 119.5 | O3—C11—H11B | 109.5 |
C4—C5—H5 | 119.5 | H11A—C11—H11B | 109.5 |
O2—C6—C5 | 124.7 (2) | O3—C11—H11C | 109.5 |
O2—C6—C7 | 115.9 (2) | H11A—C11—H11C | 109.5 |
C5—C6—C7 | 119.4 (2) | H11B—C11—H11C | 109.5 |
O3—C7—C6 | 119.9 (2) | C6—O2—C10 | 117.31 (19) |
O3—C7—C8 | 120.4 (2) | C7—O3—C11 | 112.94 (18) |
C6—C7—C8 | 119.6 (2) | C8—O4—C12 | 115.5 (2) |
C9—C8—O4 | 125.1 (3) | O52—O51—O51i | 150.1 (13) |
C9—C8—C7 | 120.8 (2) | O51—O52—O52ii | 124.1 (12) |
O4—C8—C7 | 114.1 (2) | ||
O1—C1—C2—C3 | 6.3 (3) | C6—C7—C8—O4 | 177.0 (2) |
C2i—C1—C2—C3 | −173.7 (3) | O3—C7—C8—Br1 | 4.1 (4) |
C1—C2—C3—C4 | −178.91 (19) | C6—C7—C8—Br1 | −178.4 (3) |
C2—C3—C4—C5 | −171.3 (2) | O4—C8—C9—C4 | −179.7 (2) |
C2—C3—C4—C9 | 8.4 (4) | C7—C8—C9—C4 | −1.2 (3) |
C9—C4—C5—C6 | −0.9 (3) | Br1—C8—C9—C4 | 176.0 (2) |
C3—C4—C5—C6 | 178.8 (2) | C5—C4—C9—C8 | 2.5 (3) |
C4—C5—C6—O2 | 178.4 (2) | C3—C4—C9—C8 | −177.2 (2) |
C4—C5—C6—C7 | −1.9 (3) | C5—C6—O2—C10 | −3.8 (3) |
O2—C6—C7—O3 | 0.4 (3) | C7—C6—O2—C10 | 176.5 (2) |
C5—C6—C7—O3 | −179.3 (2) | C6—C7—O3—C11 | 104.9 (2) |
O2—C6—C7—C8 | −177.1 (2) | C8—C7—O3—C11 | −77.7 (3) |
C5—C6—C7—C8 | 3.2 (3) | C9—C8—O4—C12 | −8.0 (4) |
O3—C7—C8—C9 | −179.1 (2) | C7—C8—O4—C12 | 173.4 (2) |
C6—C7—C8—C9 | −1.6 (3) | Br1—C8—O4—C12 | 10.6 (9) |
O3—C7—C8—O4 | −0.5 (3) | O51i—O51—O52—O52ii | 78.4 (19) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y, −z. |