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The relative stereochemistry of the title compound is defined by a room-temperature single-crystal X-ray study.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021688/ww6125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021688/ww6125Isup2.hkl
Contains datablock I

CCDC reference: 226946

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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
C17H16O6F(000) = 664
Mr = 316.31Dx = 1.358 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybcCell parameters from 9 reflections
a = 13.645 (5) Åθ = 9.9–34.4°
b = 8.293 (4) ŵ = 0.10 mm1
c = 14.112 (5) ÅT = 293 K
β = 104.40 (2)°Block, colourless
V = 1546.7 (11) Å30.34 × 0.21 × 0.20 mm
Z = 4
Data collection top
Syntex P21
diffractometer
θmax = 22.5°, θmin = 1.5°
Radiation source: sealed tubeh = 014
Graphite monochromatork = 08
2θω scansl = 1514
2035 measured reflections6 standard reflections every 60 min
2035 independent reflections intensity decay: none
1878 reflections with I > σ(I)
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: difference Fourier map
wR(F2) = 0.054H-atom parameters not refined
S = 1.04 w = 1/(σ2(F) + 0.0005F2)
1878 reflections(Δ/σ)max = 0.006
208 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.18 e Å3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6511 (2)0.5926 (4)0.1074 (2)0.0605 (17)
C20.5509 (2)0.5493 (4)0.1252 (2)0.068 (2)
O20.47295 (18)0.6172 (3)0.0841 (2)0.0992 (17)
C30.5531 (2)0.4102 (5)0.1940 (3)0.074 (2)
C40.6348 (2)0.4312 (3)0.2894 (2)0.0522 (16)
O40.61151 (15)0.5660 (2)0.34125 (14)0.0614 (12)
C410.5674 (3)0.5291 (4)0.4187 (3)0.083 (2)
C4a0.73911 (19)0.4685 (3)0.27194 (18)0.0401 (13)
O4a0.76482 (13)0.3227 (2)0.22637 (13)0.0482 (10)
C4a10.8611 (2)0.3068 (4)0.21758 (19)0.0485 (16)
O4a10.92462 (15)0.4077 (3)0.24450 (15)0.0628 (12)
C4a20.8745 (3)0.1505 (4)0.1706 (2)0.070 (2)
C50.8989 (2)0.6840 (3)0.5016 (2)0.0492 (15)
C60.9152 (2)0.8380 (4)0.5394 (2)0.0576 (17)
C70.8678 (2)0.9678 (4)0.4862 (2)0.0598 (18)
C80.8052 (2)0.9468 (3)0.3947 (2)0.0539 (16)
C8a0.78870 (18)0.7927 (3)0.35407 (18)0.0420 (14)
C90.7239 (2)0.7718 (3)0.2535 (2)0.0467 (15)
O90.67166 (16)0.8807 (2)0.21133 (15)0.0679 (12)
C9a0.73336 (18)0.6130 (3)0.20305 (18)0.0427 (14)
C100.8127 (2)0.4923 (3)0.37246 (19)0.0427 (14)
O100.84519 (17)0.3754 (2)0.42225 (14)0.0636 (12)
C10a0.83518 (18)0.6599 (3)0.40881 (18)0.0397 (13)
H1a0.644220.691200.072040.07600*
H1b0.671160.509740.069710.07600*
H3a0.566720.313900.162480.09400*
H3b0.489150.401700.208210.09400*
H40.636260.332560.323940.04100*
H41a0.554130.625090.449800.12500*
H41b0.612300.462630.465380.12500*
H41c0.505560.471970.394300.12500*
H4a2a0.935310.154500.148340.10800*
H4a2b0.818910.131010.117020.10800*
H4a2c0.880490.065860.217230.10800*
H50.931030.594710.538840.04900*
H60.959460.854580.602170.07200*
H70.878151.073010.513400.06400*
H80.772961.037180.358880.06800*
H9a0.795950.616340.184960.05000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.061 (2)0.070 (2)0.0450 (16)0.0082 (16)0.0018 (14)0.0034 (15)
C20.054 (2)0.078 (2)0.065 (2)0.0038 (18)0.0006 (16)0.0297 (19)
O20.0568 (15)0.120 (2)0.102 (2)0.0252 (15)0.0141 (14)0.0386 (16)
C30.0473 (18)0.085 (3)0.093 (3)0.0187 (18)0.0214 (18)0.031 (2)
C40.0576 (18)0.0413 (16)0.0633 (18)0.0107 (13)0.0259 (15)0.0082 (14)
O40.0667 (13)0.0541 (12)0.0756 (14)0.0107 (10)0.0406 (11)0.0124 (11)
C410.105 (3)0.084 (3)0.076 (2)0.002 (2)0.051 (2)0.007 (2)
C4a0.0459 (15)0.0333 (14)0.0430 (14)0.0009 (12)0.0147 (12)0.0045 (12)
O4a0.0518 (12)0.0408 (11)0.0534 (11)0.0008 (9)0.0155 (9)0.0102 (9)
C4a10.058 (2)0.0477 (18)0.0398 (15)0.0108 (15)0.0127 (14)0.0021 (13)
O4a10.0503 (12)0.0596 (14)0.0796 (15)0.0007 (11)0.0181 (11)0.0037 (11)
C4a20.088 (2)0.061 (2)0.067 (2)0.0209 (18)0.0284 (18)0.0068 (16)
C50.0510 (17)0.0522 (18)0.0446 (16)0.0020 (14)0.0125 (13)0.0009 (14)
C60.0582 (18)0.064 (2)0.0520 (17)0.0147 (16)0.0162 (15)0.0143 (16)
C70.070 (2)0.0472 (19)0.067 (2)0.0143 (16)0.0260 (17)0.0180 (16)
C80.0620 (19)0.0369 (16)0.066 (2)0.0031 (14)0.0215 (16)0.0001 (15)
C8a0.0412 (15)0.0363 (15)0.0507 (16)0.0038 (12)0.0157 (13)0.0004 (13)
C90.0440 (16)0.0413 (16)0.0560 (17)0.0003 (13)0.0147 (14)0.0089 (14)
O90.0708 (14)0.0483 (12)0.0756 (14)0.0151 (11)0.0013 (11)0.0122 (11)
C9a0.0377 (14)0.0487 (16)0.0420 (15)0.0003 (12)0.0102 (12)0.0028 (13)
C100.0505 (16)0.0394 (16)0.0406 (15)0.0010 (13)0.0158 (12)0.0018 (13)
O100.0939 (16)0.0401 (11)0.0504 (12)0.0072 (11)0.0056 (11)0.0066 (10)
C10a0.0413 (14)0.0378 (15)0.0429 (15)0.0044 (12)0.0157 (12)0.0020 (12)
Geometric parameters (Å, º) top
C1—C21.493 (5)C4a1—C4a21.487 (4)
C1—C9a1.535 (3)C4a2—H4a2a0.959
C1—H1a0.950C4a2—H4a2b0.942
C1—H1b0.950C4a2—H4a2c0.951
C2—O21.216 (4)C5—C61.380 (4)
C2—C31.503 (5)C5—C10a1.395 (3)
C3—C41.530 (4)C5—H50.950
C3—H3a0.954C6—C71.378 (4)
C3—H3b0.946C6—H60.950
C4—O41.415 (4)C7—C81.372 (4)
C4—C4a1.535 (4)C7—H70.950
C4—H40.950C8—C8a1.395 (4)
O4—C411.407 (5)C8—H80.949
C41—H41a0.948C8a—C91.484 (3)
C41—H41b0.955C8a—C10a1.403 (3)
C41—H41c0.954C9—O91.211 (3)
C4a—O4a1.453 (3)C9—C9a1.517 (4)
C4a—C9a1.532 (4)C9a—H9a0.951
C4a—C101.533 (3)C10—O101.214 (3)
O4a—C4a11.356 (4)C10—C10a1.487 (4)
C4a1—O4a11.197 (4)
C2—C1—C9a112.2 (3)O4a1—C4a1—C4a2126.2 (3)
C2—C1—H1a108.7C4a1—C4a2—H4a2a109.2
C2—C1—H1b108.9C4a1—C4a2—H4a2b110.1
C9a—C1—H1a108.8C4a1—C4a2—H4a2c109.5
C9a—C1—H1b108.8H4a2a—C4a2—H4a2b109.4
H1a—C1—H1b109.4H4a2a—C4a2—H4a2c108.6
C1—C2—O2122.5 (3)H4a2b—C4a2—H4a2c110.0
C1—C2—C3114.9 (3)C6—C5—C10a119.9 (2)
O2—C2—C3122.5 (3)C6—C5—H5120.0
C2—C3—C4112.0 (3)C10a—C5—H5120.1
C2—C3—H3a108.4C5—C6—C7120.3 (2)
C2—C3—H3b108.9C5—C6—H6119.9
C4—C3—H3a108.8C7—C6—H6119.8
C4—C3—H3b109.3C6—C7—C8120.8 (3)
H3a—C3—H3b109.5C6—C7—H7119.7
C3—C4—O4109.7 (2)C8—C7—H7119.5
C3—C4—C4a112.5 (3)C7—C8—C8a120.1 (2)
C3—C4—H4105.7C7—C8—H8119.9
O4—C4—C4a105.1 (2)C8a—C8—H8119.9
O4—C4—H4113.2C8—C8a—C9119.8 (2)
C4a—C4—H4110.8C8—C8a—C10a119.2 (2)
C4—O4—C41115.1 (2)C9—C8a—C10a121.0 (2)
O4—C41—H41a110.1C8a—C9—O9121.4 (2)
O4—C41—H41b109.6C8a—C9—C9a116.7 (2)
O4—C41—H41c109.8O9—C9—C9a121.7 (2)
H41a—C41—H41b109.2C1—C9a—C4a112.5 (2)
H41a—C41—H41c109.3C1—C9a—C9112.3 (2)
H41b—C41—H41c108.7C1—C9a—H9a106.0
C4—C4a—O4a103.8 (2)C4a—C9a—C9112.2 (2)
C4—C4a—C9a110.9 (2)C4a—C9a—H9a106.6
C4—C4a—C10107.3 (2)C9—C9a—H9a106.7
O4a—C4a—C9a110.5 (2)C4a—C10—O10119.6 (2)
O4a—C4a—C10109.99 (19)C4a—C10—C10a118.1 (2)
C9a—C4a—C10113.9 (2)O10—C10—C10a122.1 (2)
C4a—O4a—C4a1117.9 (2)C5—C10a—C8a119.7 (2)
O4a—C4a1—O4a1123.0 (3)C5—C10a—C10119.0 (2)
O4a—C4a1—C4a2110.8 (2)C8a—C10a—C10121.2 (2)
 

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