Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013036/hg6181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013036/hg6181Isup2.hkl |
CCDC reference: 274424
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.108
- Data-to-parameter ratio = 9.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.76 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11
Alert level C PLAT213_ALERT_2_C Atom O82 has ADP max/min Ratio ............. 3.40 prolat PLAT213_ALERT_2_C Atom O122 has ADP max/min Ratio ............. 3.10 prolat PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc.
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 27.50 From the CIF: _reflns_number_total 2590 Count of symmetry unique reflns 2590 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 2 ALERT level B = Potentially serious problem 7 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 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.
C16H24O11 | Dx = 1.318 Mg m−3 |
Mr = 392.35 | Melting point: 376 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 70 reflections |
a = 8.2148 (8) Å | θ = 4.6–12.5° |
b = 14.310 (2) Å | µ = 0.11 mm−1 |
c = 16.8160 (17) Å | T = 296 K |
V = 1976.8 (4) Å3 | Prism, colorless |
Z = 4 | 0.50 × 0.48 × 0.34 mm |
F(000) = 832 |
Bruker P4 diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube, FN4 | θmax = 27.5°, θmin = 1.9° |
Graphite monochromator | h = −10→3 |
2θ/ω scans | k = −18→1 |
4047 measured reflections | l = −21→1 |
2590 independent reflections | 3 standard reflections every 97 reflections |
1919 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0532P)2 + 0.1846P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2590 reflections | Δρmax = 0.14 e Å−3 |
281 parameters | Δρmin = −0.13 e Å−3 |
6 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0147 (15) |
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 | 0.7166 (3) | 0.59796 (16) | 0.43470 (13) | 0.0461 (5) | |
H1A | 0.7054 | 0.5650 | 0.3839 | 0.055* | |
C2 | 0.6396 (3) | 0.54255 (17) | 0.50160 (13) | 0.0459 (5) | |
H2A | 0.5227 | 0.5364 | 0.4912 | 0.055* | |
C3 | 0.7114 (3) | 0.44576 (17) | 0.51485 (14) | 0.0521 (6) | |
H3A | 0.8269 | 0.4525 | 0.5284 | 0.063* | |
C4 | 0.6970 (3) | 0.38103 (17) | 0.44312 (15) | 0.0517 (6) | |
H4A | 0.7536 | 0.4081 | 0.3973 | 0.062* | |
C5 | 0.7653 (4) | 0.28605 (18) | 0.46171 (18) | 0.0674 (8) | |
H5A | 0.8755 | 0.2922 | 0.4818 | 0.081* | |
H5B | 0.6997 | 0.2561 | 0.5023 | 0.081* | |
O6 | 0.8835 (2) | 0.61561 (13) | 0.45219 (9) | 0.0549 (5) | |
C7 | 0.9975 (3) | 0.5874 (2) | 0.40055 (15) | 0.0593 (7) | |
O81 | 0.9636 (5) | 0.5318 (4) | 0.3480 (5) | 0.0745 (19) | 0.75 (2) |
O82 | 0.970 (2) | 0.593 (4) | 0.3302 (5) | 0.144 (14) | 0.25 (2) |
C9 | 1.1644 (3) | 0.6147 (3) | 0.42626 (19) | 0.0728 (8) | |
H9A | 1.2382 | 0.6083 | 0.3823 | 0.109* | |
H9B | 1.1989 | 0.5749 | 0.4690 | 0.109* | |
H9C | 1.1636 | 0.6784 | 0.4440 | 0.109* | |
O10 | 0.6359 (3) | 0.68576 (11) | 0.43221 (10) | 0.0566 (5) | |
C11 | 0.6179 (4) | 0.7282 (2) | 0.36231 (15) | 0.0642 (7) | |
O121 | 0.7019 (7) | 0.7045 (3) | 0.3056 (2) | 0.0759 (19) | 0.679 (12) |
O122 | 0.569 (3) | 0.6676 (11) | 0.3131 (10) | 0.184 (11) | 0.321 (12) |
C13 | 0.5284 (4) | 0.8164 (2) | 0.36690 (17) | 0.0640 (7) | |
H13A | 0.4805 | 0.8300 | 0.3161 | 0.096* | |
H13B | 0.6017 | 0.8658 | 0.3814 | 0.096* | |
H13C | 0.4442 | 0.8114 | 0.4062 | 0.096* | |
O14 | 0.66245 (19) | 0.59364 (12) | 0.57466 (9) | 0.0492 (4) | |
C15 | 0.5282 (3) | 0.6176 (2) | 0.61711 (15) | 0.0582 (6) | |
O16 | 0.3933 (2) | 0.6064 (2) | 0.59334 (14) | 0.0960 (8) | |
C17 | 0.5737 (4) | 0.6568 (3) | 0.69593 (16) | 0.0769 (10) | |
H17A | 0.4884 | 0.6970 | 0.7146 | 0.115* | |
H17B | 0.6728 | 0.6919 | 0.6910 | 0.115* | |
H17C | 0.5895 | 0.6067 | 0.7332 | 0.115* | |
O18 | 0.6295 (3) | 0.40477 (14) | 0.58041 (10) | 0.0676 (5) | |
C19 | 0.7244 (6) | 0.3958 (3) | 0.65048 (18) | 0.0983 (13) | |
H19A | 0.6594 | 0.3686 | 0.6919 | 0.147* | |
H19B | 0.7616 | 0.4564 | 0.6670 | 0.147* | |
H19C | 0.8165 | 0.3564 | 0.6400 | 0.147* | |
O20 | 0.5262 (2) | 0.36706 (12) | 0.42450 (9) | 0.0548 (4) | |
C21 | 0.4681 (4) | 0.4017 (2) | 0.35577 (16) | 0.0619 (7) | |
O221 | 0.536 (2) | 0.4580 (15) | 0.3157 (12) | 0.096 (4) | 0.63 (6) |
O222 | 0.567 (3) | 0.424 (3) | 0.3051 (8) | 0.093 (7) | 0.37 (6) |
C23 | 0.2941 (4) | 0.3772 (2) | 0.3443 (2) | 0.0765 (9) | |
H23A | 0.2441 | 0.4219 | 0.3095 | 0.115* | |
H23B | 0.2395 | 0.3778 | 0.3948 | 0.115* | |
H23C | 0.2862 | 0.3159 | 0.3214 | 0.115* | |
O24 | 0.7657 (3) | 0.22994 (13) | 0.39087 (12) | 0.0699 (6) | |
C25 | 0.7028 (4) | 0.1445 (2) | 0.3948 (2) | 0.0675 (7) | |
O26 | 0.6419 (4) | 0.11247 (18) | 0.45370 (15) | 0.0971 (8) | |
C27 | 0.7169 (6) | 0.0941 (3) | 0.3179 (2) | 0.0955 (12) | |
H27A | 0.7059 | 0.0282 | 0.3268 | 0.143* | |
H27B | 0.8213 | 0.1068 | 0.2946 | 0.143* | |
H27C | 0.6326 | 0.1149 | 0.2825 | 0.143* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0457 (12) | 0.0522 (12) | 0.0403 (11) | 0.0014 (12) | −0.0021 (10) | −0.0070 (11) |
C2 | 0.0419 (12) | 0.0572 (13) | 0.0385 (10) | −0.0024 (11) | −0.0038 (10) | −0.0061 (10) |
C3 | 0.0500 (13) | 0.0572 (13) | 0.0492 (13) | −0.0013 (12) | −0.0069 (12) | 0.0045 (11) |
C4 | 0.0493 (13) | 0.0531 (13) | 0.0527 (13) | 0.0005 (11) | −0.0045 (11) | 0.0008 (12) |
C5 | 0.0744 (19) | 0.0567 (14) | 0.0712 (17) | 0.0112 (15) | −0.0245 (17) | −0.0054 (14) |
O6 | 0.0465 (9) | 0.0752 (11) | 0.0429 (8) | −0.0056 (9) | 0.0033 (7) | −0.0123 (9) |
C7 | 0.0518 (15) | 0.0749 (17) | 0.0511 (14) | 0.0099 (14) | 0.0033 (12) | −0.0047 (13) |
O81 | 0.055 (2) | 0.095 (3) | 0.073 (3) | 0.0090 (19) | 0.0074 (19) | −0.036 (2) |
O82 | 0.095 (8) | 0.31 (4) | 0.030 (5) | −0.063 (16) | 0.008 (5) | −0.015 (10) |
C9 | 0.0508 (15) | 0.097 (2) | 0.0704 (17) | −0.0020 (16) | 0.0048 (14) | −0.0094 (18) |
O10 | 0.0777 (12) | 0.0516 (9) | 0.0404 (8) | 0.0084 (9) | 0.0019 (9) | 0.0006 (7) |
C11 | 0.0746 (18) | 0.0750 (17) | 0.0430 (13) | 0.0197 (17) | −0.0092 (14) | −0.0042 (13) |
O121 | 0.119 (4) | 0.072 (2) | 0.0368 (18) | 0.030 (2) | 0.020 (2) | 0.0067 (13) |
O122 | 0.23 (2) | 0.189 (14) | 0.137 (10) | 0.135 (15) | −0.129 (13) | −0.097 (10) |
C13 | 0.0597 (16) | 0.0728 (17) | 0.0596 (15) | 0.0101 (15) | −0.0039 (14) | 0.0054 (14) |
O14 | 0.0419 (8) | 0.0657 (9) | 0.0400 (7) | −0.0035 (8) | 0.0010 (7) | −0.0051 (8) |
C15 | 0.0483 (14) | 0.0737 (16) | 0.0526 (14) | 0.0031 (14) | 0.0087 (12) | −0.0024 (13) |
O16 | 0.0439 (11) | 0.156 (2) | 0.0884 (15) | 0.0110 (15) | −0.0002 (11) | −0.0349 (17) |
C17 | 0.0695 (19) | 0.110 (3) | 0.0517 (15) | −0.0034 (19) | 0.0141 (14) | −0.0176 (16) |
O18 | 0.0822 (13) | 0.0739 (12) | 0.0468 (9) | −0.0007 (12) | −0.0026 (10) | 0.0148 (9) |
C19 | 0.137 (3) | 0.103 (3) | 0.0551 (16) | 0.033 (3) | −0.020 (2) | 0.0164 (18) |
O20 | 0.0536 (9) | 0.0650 (10) | 0.0457 (8) | −0.0022 (9) | −0.0078 (8) | 0.0073 (8) |
C21 | 0.084 (2) | 0.0523 (14) | 0.0493 (14) | −0.0062 (16) | −0.0240 (15) | 0.0004 (12) |
O221 | 0.129 (5) | 0.079 (6) | 0.078 (5) | −0.041 (5) | −0.060 (4) | 0.032 (4) |
O222 | 0.135 (10) | 0.102 (14) | 0.041 (5) | −0.066 (9) | −0.012 (6) | 0.015 (6) |
C23 | 0.080 (2) | 0.0739 (18) | 0.0754 (18) | 0.0011 (18) | −0.0287 (18) | −0.0046 (16) |
O24 | 0.0855 (14) | 0.0542 (10) | 0.0699 (11) | 0.0083 (11) | −0.0017 (12) | −0.0036 (9) |
C25 | 0.0698 (18) | 0.0636 (17) | 0.0692 (17) | 0.0006 (16) | 0.0003 (17) | −0.0047 (15) |
O26 | 0.117 (2) | 0.0909 (15) | 0.0836 (16) | −0.0287 (17) | 0.0153 (16) | −0.0098 (15) |
C27 | 0.125 (3) | 0.081 (2) | 0.081 (2) | −0.004 (2) | 0.011 (2) | −0.0184 (19) |
C1—O10 | 1.421 (3) | C13—H13A | 0.9600 |
C1—O6 | 1.424 (3) | C13—H13B | 0.9600 |
C1—C2 | 1.515 (3) | C13—H13C | 0.9600 |
C1—H1A | 0.9800 | O14—C15 | 1.358 (3) |
C2—O14 | 1.442 (3) | C15—O16 | 1.188 (3) |
C2—C3 | 1.522 (4) | C15—C17 | 1.487 (4) |
C2—H2A | 0.9800 | C17—H17A | 0.9600 |
C3—O18 | 1.419 (3) | C17—H17B | 0.9600 |
C3—C4 | 1.526 (3) | C17—H17C | 0.9600 |
C3—H3A | 0.9800 | O18—C19 | 1.419 (4) |
C4—O20 | 1.451 (3) | C19—H19A | 0.9600 |
C4—C5 | 1.503 (4) | C19—H19B | 0.9600 |
C4—H4A | 0.9800 | C19—H19C | 0.9600 |
C5—O24 | 1.437 (3) | O20—C21 | 1.345 (3) |
C5—H5A | 0.9700 | C21—O221 | 1.191 (7) |
C5—H5B | 0.9700 | C21—O222 | 1.222 (9) |
O6—C7 | 1.340 (3) | C21—C23 | 1.484 (4) |
C7—O82 | 1.207 (9) | C23—H23A | 0.9600 |
C7—O81 | 1.221 (4) | C23—H23B | 0.9600 |
C7—C9 | 1.490 (4) | C23—H23C | 0.9600 |
C9—H9A | 0.9600 | O24—C25 | 1.329 (4) |
C9—H9B | 0.9600 | C25—O26 | 1.200 (4) |
C9—H9C | 0.9600 | C25—C27 | 1.486 (5) |
O10—C11 | 1.331 (3) | C27—H27A | 0.9600 |
C11—O121 | 1.224 (4) | C27—H27B | 0.9600 |
C11—O122 | 1.263 (9) | C27—H27C | 0.9600 |
C11—C13 | 1.463 (4) | ||
O10—C1—O6 | 107.35 (19) | O10—C11—C13 | 113.7 (2) |
O10—C1—C2 | 106.85 (18) | C11—C13—H13A | 109.5 |
O6—C1—C2 | 109.95 (19) | C11—C13—H13B | 109.5 |
O10—C1—H1A | 110.9 | H13A—C13—H13B | 109.5 |
O6—C1—H1A | 110.9 | C11—C13—H13C | 109.5 |
C2—C1—H1A | 110.9 | H13A—C13—H13C | 109.5 |
O14—C2—C1 | 108.25 (18) | H13B—C13—H13C | 109.5 |
O14—C2—C3 | 106.64 (18) | C15—O14—C2 | 118.05 (19) |
C1—C2—C3 | 115.0 (2) | O16—C15—O14 | 123.1 (2) |
O14—C2—H2A | 108.9 | O16—C15—C17 | 125.8 (3) |
C1—C2—H2A | 108.9 | O14—C15—C17 | 111.1 (2) |
C3—C2—H2A | 108.9 | C15—C17—H17A | 109.5 |
O18—C3—C2 | 107.8 (2) | C15—C17—H17B | 109.5 |
O18—C3—C4 | 109.1 (2) | H17A—C17—H17B | 109.5 |
C2—C3—C4 | 114.00 (19) | C15—C17—H17C | 109.5 |
O18—C3—H3A | 108.6 | H17A—C17—H17C | 109.5 |
C2—C3—H3A | 108.6 | H17B—C17—H17C | 109.5 |
C4—C3—H3A | 108.6 | C3—O18—C19 | 115.0 (3) |
O20—C4—C5 | 106.3 (2) | O18—C19—H19A | 109.5 |
O20—C4—C3 | 109.2 (2) | O18—C19—H19B | 109.5 |
C5—C4—C3 | 110.8 (2) | H19A—C19—H19B | 109.5 |
O20—C4—H4A | 110.1 | O18—C19—H19C | 109.5 |
C5—C4—H4A | 110.1 | H19A—C19—H19C | 109.5 |
C3—C4—H4A | 110.1 | H19B—C19—H19C | 109.5 |
O24—C5—C4 | 109.5 (2) | C21—O20—C4 | 118.5 (2) |
O24—C5—H5A | 109.8 | O221—C21—O20 | 124.7 (6) |
C4—C5—H5A | 109.8 | O222—C21—O20 | 117.4 (16) |
O24—C5—H5B | 109.8 | O221—C21—C23 | 122.6 (6) |
C4—C5—H5B | 109.8 | O222—C21—C23 | 127.9 (11) |
H5A—C5—H5B | 108.2 | O20—C21—C23 | 111.5 (3) |
C7—O6—C1 | 119.04 (19) | C21—C23—H23A | 109.5 |
O82—C7—O6 | 119.1 (15) | C21—C23—H23B | 109.5 |
O81—C7—O6 | 120.4 (4) | H23A—C23—H23B | 109.5 |
O82—C7—C9 | 116.0 (10) | C21—C23—H23C | 109.5 |
O81—C7—C9 | 126.2 (3) | H23A—C23—H23C | 109.5 |
O6—C7—C9 | 112.1 (2) | H23B—C23—H23C | 109.5 |
C7—C9—H9A | 109.5 | C25—O24—C5 | 118.2 (2) |
C7—C9—H9B | 109.5 | O26—C25—O24 | 123.7 (3) |
H9A—C9—H9B | 109.5 | O26—C25—C27 | 124.5 (3) |
C7—C9—H9C | 109.5 | O24—C25—C27 | 111.9 (3) |
H9A—C9—H9C | 109.5 | C25—C27—H27A | 109.5 |
H9B—C9—H9C | 109.5 | C25—C27—H27B | 109.5 |
C11—O10—C1 | 118.74 (19) | H27A—C27—H27B | 109.5 |
O121—C11—O10 | 119.9 (3) | C25—C27—H27C | 109.5 |
O122—C11—O10 | 107.5 (10) | H27A—C27—H27C | 109.5 |
O121—C11—C13 | 124.3 (3) | H27B—C27—H27C | 109.5 |
O122—C11—C13 | 117.9 (5) | ||
O10—C1—C2—O14 | −60.1 (2) | O6—C1—O10—C11 | 94.5 (3) |
O6—C1—C2—O14 | 56.1 (2) | C2—C1—O10—C11 | −147.6 (2) |
O10—C1—C2—C3 | −179.22 (19) | C1—O10—C11—O121 | −17.6 (5) |
O6—C1—C2—C3 | −63.0 (2) | C1—O10—C11—O122 | 45.6 (11) |
O14—C2—C3—O18 | 58.4 (2) | C1—O10—C11—C13 | 178.1 (2) |
C1—C2—C3—O18 | 178.39 (19) | C1—C2—O14—C15 | 122.5 (2) |
O14—C2—C3—C4 | 179.6 (2) | C3—C2—O14—C15 | −113.2 (2) |
C1—C2—C3—C4 | −60.4 (3) | C2—O14—C15—O16 | −7.5 (4) |
O18—C3—C4—O20 | 59.3 (3) | C2—O14—C15—C17 | 171.5 (2) |
C2—C3—C4—O20 | −61.2 (3) | C2—C3—O18—C19 | −109.5 (3) |
O18—C3—C4—C5 | −57.5 (3) | C4—C3—O18—C19 | 126.2 (3) |
C2—C3—C4—C5 | −178.1 (2) | C5—C4—O20—C21 | −127.2 (2) |
O20—C4—C5—O24 | 67.4 (3) | C3—C4—O20—C21 | 113.1 (2) |
C3—C4—C5—O24 | −174.0 (2) | C4—O20—C21—O221 | −15.1 (18) |
O10—C1—O6—C7 | −120.9 (2) | C4—O20—C21—O222 | 16 (2) |
C2—C1—O6—C7 | 123.2 (2) | C4—O20—C21—C23 | 177.2 (2) |
C1—O6—C7—O82 | 37 (3) | C4—C5—O24—C25 | −130.5 (3) |
C1—O6—C7—O81 | −14.5 (6) | C5—O24—C25—O26 | 2.0 (5) |
C1—O6—C7—C9 | 177.7 (2) | C5—O24—C25—C27 | −178.1 (3) |
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