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The crystal structure of the title compound, C8H6O4, consists of layers of characteristic dimers formed by inter­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010695/jh2005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010695/jh2005Isup2.hkl
Contains datablock I

CCDC reference: 608427

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.134
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B CELLV02_ALERT_1_B The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 4 Calculated cell volume su = 17.23 Cell volume su given = 12.00
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.16
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL/NT.

(I) top
Crystal data top
C8H6O4F(000) = 172
Mr = 166.13Dx = 1.555 Mg m3
Triclinic, P1Melting point: 502 K
a = 7.0685 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.1553 (14) ÅCell parameters from 2904 reflections
c = 8.1436 (16) Åθ = 3.2–27.5°
α = 90.39 (3)°µ = 0.13 mm1
β = 107.51 (3)°T = 298 K
γ = 114.06 (3)°Column, colorless
V = 354.67 (12) Å30.37 × 0.26 × 0.15 mm
Z = 2
Data collection top
Rigaku r-axis rapid IP area detector
diffractometer
1613 independent reflections
Radiation source: rotating anode1158 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω? φ? scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
SADABS
h = 99
Tmin = 0.954, Tmax = 0.981k = 89
3553 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.085P)2]
where P = (Fo2 + 2Fc2)/3
1613 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4020 (2)0.06085 (19)1.28801 (14)0.0527 (4)
O20.3899 (2)0.3753 (2)1.32834 (13)0.0603 (4)
O30.0949 (2)0.55282 (19)0.72403 (14)0.0592 (4)
H3B0.05400.59030.63020.089*
O40.0276 (2)0.27784 (19)0.54766 (13)0.0532 (4)
C10.4323 (3)0.2173 (3)1.4156 (2)0.0529 (4)
H1A0.33250.15871.48070.063*
H1B0.58160.27481.49660.063*
C20.3225 (2)0.1155 (2)1.13044 (19)0.0364 (4)
C30.2581 (3)0.0089 (2)0.96815 (19)0.0398 (4)
H3A0.26400.11730.95270.048*
C40.1835 (2)0.0996 (2)0.82812 (18)0.0374 (4)
H4A0.13830.03230.71570.045*
C50.1745 (2)0.2874 (2)0.85107 (17)0.0340 (3)
C60.0941 (2)0.3767 (2)0.69805 (18)0.0375 (4)
C70.2418 (2)0.3946 (2)1.01842 (18)0.0382 (4)
H7A0.23670.52091.03560.046*
C80.3150 (2)0.3031 (2)1.15476 (17)0.0379 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0733 (8)0.0535 (7)0.0370 (6)0.0380 (6)0.0105 (5)0.0154 (5)
O20.1010 (10)0.0549 (8)0.0257 (5)0.0453 (7)0.0054 (6)0.0051 (5)
O30.0983 (10)0.0482 (7)0.0334 (6)0.0445 (7)0.0064 (6)0.0065 (5)
O40.0810 (9)0.0490 (7)0.0274 (5)0.0330 (6)0.0079 (5)0.0044 (5)
C10.0727 (11)0.0565 (10)0.0337 (7)0.0352 (9)0.0127 (7)0.0141 (7)
C20.0377 (8)0.0384 (8)0.0341 (7)0.0183 (6)0.0106 (6)0.0112 (6)
C30.0477 (9)0.0346 (7)0.0400 (7)0.0215 (7)0.0133 (6)0.0050 (6)
C40.0441 (8)0.0348 (8)0.0322 (6)0.0170 (6)0.0111 (6)0.0015 (6)
C50.0378 (8)0.0331 (7)0.0283 (7)0.0132 (6)0.0100 (6)0.0055 (6)
C60.0470 (8)0.0352 (7)0.0294 (7)0.0187 (6)0.0099 (6)0.0045 (6)
C70.0513 (9)0.0320 (7)0.0301 (7)0.0197 (7)0.0092 (6)0.0045 (6)
C80.0458 (8)0.0371 (8)0.0277 (6)0.0176 (6)0.0081 (6)0.0041 (6)
Geometric parameters (Å, º) top
O1—C21.366 (2)C2—C81.380 (2)
O1—C11.426 (2)C3—C41.388 (2)
O2—C81.365 (2)C3—H3A0.9300
O2—C11.426 (2)C4—C51.385 (2)
O3—C61.274 (2)C4—H4A0.9300
O3—H3B0.8200C5—C71.404 (2)
O4—C61.262 (2)C5—C61.472 (2)
C1—H1A0.9700C7—C81.367 (2)
C1—H1B0.9700C7—H7A0.9300
C2—C31.370 (2)
C2—O1—C1105.75 (13)C5—C4—C3121.90 (14)
C8—O2—C1105.74 (14)C5—C4—H4A119.1
C6—O3—H3B109.5C3—C4—H4A119.1
O2—C1—O1108.28 (13)C4—C5—C7120.98 (13)
O2—C1—H1A110.0C4—C5—C6119.67 (13)
O1—C1—H1A110.0C7—C5—C6119.34 (14)
O2—C1—H1B110.0O4—C6—O3122.62 (13)
O1—C1—H1B110.0O4—C6—C5119.48 (14)
H1A—C1—H1B108.4O3—C6—C5117.91 (13)
O1—C2—C3127.86 (15)C8—C7—C5116.32 (15)
O1—C2—C8109.86 (14)C8—C7—H7A121.8
C3—C2—C8122.28 (13)C5—C7—H7A121.8
C2—C3—C4116.29 (15)O2—C8—C7127.77 (15)
C2—C3—H3A121.9O2—C8—C2110.00 (13)
C4—C3—H3A121.9C7—C8—C2122.22 (14)
C8—O2—C1—O16.0 (2)C7—C5—C6—O32.0 (2)
C2—O1—C1—O25.88 (19)C4—C5—C7—C80.1 (2)
C1—O1—C2—C3176.77 (16)C6—C5—C7—C8179.89 (14)
C1—O1—C2—C83.54 (18)C1—O2—C8—C7176.33 (17)
O1—C2—C3—C4179.87 (15)C1—O2—C8—C23.86 (19)
C8—C2—C3—C40.2 (2)C5—C7—C8—O2179.64 (15)
C2—C3—C4—C50.0 (2)C5—C7—C8—C20.2 (2)
C3—C4—C5—C70.2 (2)O1—C2—C8—O20.21 (19)
C3—C4—C5—C6179.99 (14)C3—C2—C8—O2179.51 (14)
C4—C5—C6—O42.2 (2)O1—C2—C8—C7179.97 (15)
C7—C5—C6—O4177.97 (13)C3—C2—C8—C70.3 (3)
C4—C5—C6—O3177.76 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···O4i0.821.812.618 (2)167
Symmetry code: (i) x, y+1, z+1.
 

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