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organic compounds
The relative stereochemistry of the title compound is defined by a room-temperature single-crystal X-ray study.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021688/ww6125sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021688/ww6125Isup2.hkl |
CCDC reference: 226946
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.054
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF012_ALERT_1_A _diffrn_reflns_av_R_equivalents is missing R factor for symmetry-equivalent intensities. The following tests will not be performed RINTA
Author Response: Only a unique dataset was collected for reasons given in _publ_section_exptl_prep and below |
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5393
Author Response: Instability of the material dictated, with the available instrumentation at the time, measurement of a unique data set within a limited 2theta range. |
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 22.54 Deg.
Author Response: see above |
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low .............. 22.54 Deg.
Author Response: see above |
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda -0.7340 Proportion of unique data used 0.9229 Ratio reflections to parameters 9.0288 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.03 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
4 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: Syntex Software (Syntex, 1973); cell refinement: Syntex Software; data reduction: Xtal3.5 (Hall et al., 1995); program(s) used to solve structure: Xtal3.5; program(s) used to refine structure: Xtal3.5 CRYLSQ; molecular graphics: Xtal3.5; software used to prepare material for publication: Xtal3.5 BONDLA CIFIO.
(I) top
Crystal data top
C17H16O6 | F(000) = 664 |
Mr = 316.31 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 9 reflections |
a = 13.645 (5) Å | θ = 9.9–34.4° |
b = 8.293 (4) Å | µ = 0.10 mm−1 |
c = 14.112 (5) Å | T = 293 K |
β = 104.40 (2)° | Block, colourless |
V = 1546.7 (11) Å3 | 0.34 × 0.21 × 0.20 mm |
Z = 4 |
Data collection top
Syntex P21 diffractometer | θmax = 22.5°, θmin = 1.5° |
Radiation source: sealed tube | h = 0→14 |
Graphite monochromator | k = 0→8 |
2θ–ω scans | l = −15→14 |
2035 measured reflections | 6 standard reflections every 60 min |
2035 independent reflections | intensity decay: none |
1878 reflections with I > σ(I) |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.054 | H-atom parameters not refined |
S = 1.04 | w = 1/(σ2(F) + 0.0005F2) |
1878 reflections | (Δ/σ)max = 0.006 |
208 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
0 constraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.6511 (2) | 0.5926 (4) | 0.1074 (2) | 0.0605 (17) | |
C2 | 0.5509 (2) | 0.5493 (4) | 0.1252 (2) | 0.068 (2) | |
O2 | 0.47295 (18) | 0.6172 (3) | 0.0841 (2) | 0.0992 (17) | |
C3 | 0.5531 (2) | 0.4102 (5) | 0.1940 (3) | 0.074 (2) | |
C4 | 0.6348 (2) | 0.4312 (3) | 0.2894 (2) | 0.0522 (16) | |
O4 | 0.61151 (15) | 0.5660 (2) | 0.34125 (14) | 0.0614 (12) | |
C41 | 0.5674 (3) | 0.5291 (4) | 0.4187 (3) | 0.083 (2) | |
C4a | 0.73911 (19) | 0.4685 (3) | 0.27194 (18) | 0.0401 (13) | |
O4a | 0.76482 (13) | 0.3227 (2) | 0.22637 (13) | 0.0482 (10) | |
C4a1 | 0.8611 (2) | 0.3068 (4) | 0.21758 (19) | 0.0485 (16) | |
O4a1 | 0.92462 (15) | 0.4077 (3) | 0.24450 (15) | 0.0628 (12) | |
C4a2 | 0.8745 (3) | 0.1505 (4) | 0.1706 (2) | 0.070 (2) | |
C5 | 0.8989 (2) | 0.6840 (3) | 0.5016 (2) | 0.0492 (15) | |
C6 | 0.9152 (2) | 0.8380 (4) | 0.5394 (2) | 0.0576 (17) | |
C7 | 0.8678 (2) | 0.9678 (4) | 0.4862 (2) | 0.0598 (18) | |
C8 | 0.8052 (2) | 0.9468 (3) | 0.3947 (2) | 0.0539 (16) | |
C8a | 0.78870 (18) | 0.7927 (3) | 0.35407 (18) | 0.0420 (14) | |
C9 | 0.7239 (2) | 0.7718 (3) | 0.2535 (2) | 0.0467 (15) | |
O9 | 0.67166 (16) | 0.8807 (2) | 0.21133 (15) | 0.0679 (12) | |
C9a | 0.73336 (18) | 0.6130 (3) | 0.20305 (18) | 0.0427 (14) | |
C10 | 0.8127 (2) | 0.4923 (3) | 0.37246 (19) | 0.0427 (14) | |
O10 | 0.84519 (17) | 0.3754 (2) | 0.42225 (14) | 0.0636 (12) | |
C10a | 0.83518 (18) | 0.6599 (3) | 0.40881 (18) | 0.0397 (13) | |
H1a | 0.64422 | 0.69120 | 0.07204 | 0.07600* | |
H1b | 0.67116 | 0.50974 | 0.06971 | 0.07600* | |
H3a | 0.56672 | 0.31390 | 0.16248 | 0.09400* | |
H3b | 0.48915 | 0.40170 | 0.20821 | 0.09400* | |
H4 | 0.63626 | 0.33256 | 0.32394 | 0.04100* | |
H41a | 0.55413 | 0.62509 | 0.44980 | 0.12500* | |
H41b | 0.61230 | 0.46263 | 0.46538 | 0.12500* | |
H41c | 0.50556 | 0.47197 | 0.39430 | 0.12500* | |
H4a2a | 0.93531 | 0.15450 | 0.14834 | 0.10800* | |
H4a2b | 0.81891 | 0.13101 | 0.11702 | 0.10800* | |
H4a2c | 0.88049 | 0.06586 | 0.21723 | 0.10800* | |
H5 | 0.93103 | 0.59471 | 0.53884 | 0.04900* | |
H6 | 0.95946 | 0.85458 | 0.60217 | 0.07200* | |
H7 | 0.87815 | 1.07301 | 0.51340 | 0.06400* | |
H8 | 0.77296 | 1.03718 | 0.35888 | 0.06800* | |
H9a | 0.79595 | 0.61634 | 0.18496 | 0.05000* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.061 (2) | 0.070 (2) | 0.0450 (16) | 0.0082 (16) | 0.0018 (14) | −0.0034 (15) |
C2 | 0.054 (2) | 0.078 (2) | 0.065 (2) | 0.0038 (18) | 0.0006 (16) | −0.0297 (19) |
O2 | 0.0568 (15) | 0.120 (2) | 0.102 (2) | 0.0252 (15) | −0.0141 (14) | −0.0386 (16) |
C3 | 0.0473 (18) | 0.085 (3) | 0.093 (3) | −0.0187 (18) | 0.0214 (18) | −0.031 (2) |
C4 | 0.0576 (18) | 0.0413 (16) | 0.0633 (18) | −0.0107 (13) | 0.0259 (15) | −0.0082 (14) |
O4 | 0.0667 (13) | 0.0541 (12) | 0.0756 (14) | −0.0107 (10) | 0.0406 (11) | −0.0124 (11) |
C41 | 0.105 (3) | 0.084 (3) | 0.076 (2) | −0.002 (2) | 0.051 (2) | −0.007 (2) |
C4a | 0.0459 (15) | 0.0333 (14) | 0.0430 (14) | −0.0009 (12) | 0.0147 (12) | −0.0045 (12) |
O4a | 0.0518 (12) | 0.0408 (11) | 0.0534 (11) | −0.0008 (9) | 0.0155 (9) | −0.0102 (9) |
C4a1 | 0.058 (2) | 0.0477 (18) | 0.0398 (15) | 0.0108 (15) | 0.0127 (14) | 0.0021 (13) |
O4a1 | 0.0503 (12) | 0.0596 (14) | 0.0796 (15) | 0.0007 (11) | 0.0181 (11) | −0.0037 (11) |
C4a2 | 0.088 (2) | 0.061 (2) | 0.067 (2) | 0.0209 (18) | 0.0284 (18) | −0.0068 (16) |
C5 | 0.0510 (17) | 0.0522 (18) | 0.0446 (16) | −0.0020 (14) | 0.0125 (13) | −0.0009 (14) |
C6 | 0.0582 (18) | 0.064 (2) | 0.0520 (17) | −0.0147 (16) | 0.0162 (15) | −0.0143 (16) |
C7 | 0.070 (2) | 0.0472 (19) | 0.067 (2) | −0.0143 (16) | 0.0260 (17) | −0.0180 (16) |
C8 | 0.0620 (19) | 0.0369 (16) | 0.066 (2) | −0.0031 (14) | 0.0215 (16) | 0.0001 (15) |
C8a | 0.0412 (15) | 0.0363 (15) | 0.0507 (16) | −0.0038 (12) | 0.0157 (13) | −0.0004 (13) |
C9 | 0.0440 (16) | 0.0413 (16) | 0.0560 (17) | −0.0003 (13) | 0.0147 (14) | 0.0089 (14) |
O9 | 0.0708 (14) | 0.0483 (12) | 0.0756 (14) | 0.0151 (11) | 0.0013 (11) | 0.0122 (11) |
C9a | 0.0377 (14) | 0.0487 (16) | 0.0420 (15) | 0.0003 (12) | 0.0102 (12) | 0.0028 (13) |
C10 | 0.0505 (16) | 0.0394 (16) | 0.0406 (15) | 0.0010 (13) | 0.0158 (12) | 0.0018 (13) |
O10 | 0.0939 (16) | 0.0401 (11) | 0.0504 (12) | 0.0072 (11) | 0.0056 (11) | 0.0066 (10) |
C10a | 0.0413 (14) | 0.0378 (15) | 0.0429 (15) | −0.0044 (12) | 0.0157 (12) | −0.0020 (12) |
Geometric parameters (Å, º) top
C1—C2 | 1.493 (5) | C4a1—C4a2 | 1.487 (4) |
C1—C9a | 1.535 (3) | C4a2—H4a2a | 0.959 |
C1—H1a | 0.950 | C4a2—H4a2b | 0.942 |
C1—H1b | 0.950 | C4a2—H4a2c | 0.951 |
C2—O2 | 1.216 (4) | C5—C6 | 1.380 (4) |
C2—C3 | 1.503 (5) | C5—C10a | 1.395 (3) |
C3—C4 | 1.530 (4) | C5—H5 | 0.950 |
C3—H3a | 0.954 | C6—C7 | 1.378 (4) |
C3—H3b | 0.946 | C6—H6 | 0.950 |
C4—O4 | 1.415 (4) | C7—C8 | 1.372 (4) |
C4—C4a | 1.535 (4) | C7—H7 | 0.950 |
C4—H4 | 0.950 | C8—C8a | 1.395 (4) |
O4—C41 | 1.407 (5) | C8—H8 | 0.949 |
C41—H41a | 0.948 | C8a—C9 | 1.484 (3) |
C41—H41b | 0.955 | C8a—C10a | 1.403 (3) |
C41—H41c | 0.954 | C9—O9 | 1.211 (3) |
C4a—O4a | 1.453 (3) | C9—C9a | 1.517 (4) |
C4a—C9a | 1.532 (4) | C9a—H9a | 0.951 |
C4a—C10 | 1.533 (3) | C10—O10 | 1.214 (3) |
O4a—C4a1 | 1.356 (4) | C10—C10a | 1.487 (4) |
C4a1—O4a1 | 1.197 (4) | ||
C2—C1—C9a | 112.2 (3) | O4a1—C4a1—C4a2 | 126.2 (3) |
C2—C1—H1a | 108.7 | C4a1—C4a2—H4a2a | 109.2 |
C2—C1—H1b | 108.9 | C4a1—C4a2—H4a2b | 110.1 |
C9a—C1—H1a | 108.8 | C4a1—C4a2—H4a2c | 109.5 |
C9a—C1—H1b | 108.8 | H4a2a—C4a2—H4a2b | 109.4 |
H1a—C1—H1b | 109.4 | H4a2a—C4a2—H4a2c | 108.6 |
C1—C2—O2 | 122.5 (3) | H4a2b—C4a2—H4a2c | 110.0 |
C1—C2—C3 | 114.9 (3) | C6—C5—C10a | 119.9 (2) |
O2—C2—C3 | 122.5 (3) | C6—C5—H5 | 120.0 |
C2—C3—C4 | 112.0 (3) | C10a—C5—H5 | 120.1 |
C2—C3—H3a | 108.4 | C5—C6—C7 | 120.3 (2) |
C2—C3—H3b | 108.9 | C5—C6—H6 | 119.9 |
C4—C3—H3a | 108.8 | C7—C6—H6 | 119.8 |
C4—C3—H3b | 109.3 | C6—C7—C8 | 120.8 (3) |
H3a—C3—H3b | 109.5 | C6—C7—H7 | 119.7 |
C3—C4—O4 | 109.7 (2) | C8—C7—H7 | 119.5 |
C3—C4—C4a | 112.5 (3) | C7—C8—C8a | 120.1 (2) |
C3—C4—H4 | 105.7 | C7—C8—H8 | 119.9 |
O4—C4—C4a | 105.1 (2) | C8a—C8—H8 | 119.9 |
O4—C4—H4 | 113.2 | C8—C8a—C9 | 119.8 (2) |
C4a—C4—H4 | 110.8 | C8—C8a—C10a | 119.2 (2) |
C4—O4—C41 | 115.1 (2) | C9—C8a—C10a | 121.0 (2) |
O4—C41—H41a | 110.1 | C8a—C9—O9 | 121.4 (2) |
O4—C41—H41b | 109.6 | C8a—C9—C9a | 116.7 (2) |
O4—C41—H41c | 109.8 | O9—C9—C9a | 121.7 (2) |
H41a—C41—H41b | 109.2 | C1—C9a—C4a | 112.5 (2) |
H41a—C41—H41c | 109.3 | C1—C9a—C9 | 112.3 (2) |
H41b—C41—H41c | 108.7 | C1—C9a—H9a | 106.0 |
C4—C4a—O4a | 103.8 (2) | C4a—C9a—C9 | 112.2 (2) |
C4—C4a—C9a | 110.9 (2) | C4a—C9a—H9a | 106.6 |
C4—C4a—C10 | 107.3 (2) | C9—C9a—H9a | 106.7 |
O4a—C4a—C9a | 110.5 (2) | C4a—C10—O10 | 119.6 (2) |
O4a—C4a—C10 | 109.99 (19) | C4a—C10—C10a | 118.1 (2) |
C9a—C4a—C10 | 113.9 (2) | O10—C10—C10a | 122.1 (2) |
C4a—O4a—C4a1 | 117.9 (2) | C5—C10a—C8a | 119.7 (2) |
O4a—C4a1—O4a1 | 123.0 (3) | C5—C10a—C10 | 119.0 (2) |
O4a—C4a1—C4a2 | 110.8 (2) | C8a—C10a—C10 | 121.2 (2) |
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