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In the solid state, the structure of the title compound, C10H8O2, is stabilized by both van der Waals interactions and O—H...O intermolecular hydrogen bonds with O...O distances of 2.714 (3) and 2.831 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032453/ac6141sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032453/ac6141Isup2.hkl
Contains datablock I

CCDC reference: 262464

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.038
  • wR factor = 0.121
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 27.44 From the CIF: _reflns_number_total 994 Count of symmetry unique reflns 994 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 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 1 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: KM4B8 (Gałdecki et al., 1996); cell refinement: KM4B8; data reduction: KM4B8; program(s) used to solve structure: Please provide missing details; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

Naphthalene-2,7-diol top
Crystal data top
C10H8O2F(000) = 336
Mr = 160.16Dx = 1.345 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2nCell parameters from 20 reflections
a = 7.872 (2) Åθ = 5.2–20.0°
b = 17.463 (3) ŵ = 0.09 mm1
c = 5.754 (2) ÅT = 293 K
V = 791.0 (3) Å3Column, colourless
Z = 40.4 × 0.06 × 0.03 mm
Data collection top
Kuma KM-4
diffractometer
740 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.005
Graphite monochromatorθmax = 27.4°, θmin = 2.3°
ω/2θ scansh = 1010
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
k = 2222
Tmin = 0.986, Tmax = 0.998l = 77
1988 measured reflections3 standard reflections every 50 reflections
994 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0043P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max = 0.035
994 reflectionsΔρmax = 0.10 e Å3
115 parametersΔρmin = 0.12 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (4)
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
O10.7241 (3)0.32403 (12)0.5971 (6)0.0864 (8)
H10.80660.29880.55600.130*
O20.5763 (3)0.72257 (11)0.8665 (6)0.0862 (8)
H20.52080.70320.97180.129*
C40.7866 (4)0.55519 (18)0.4333 (6)0.0717 (8)
C90.7023 (4)0.53286 (16)0.6426 (6)0.0648 (8)
C100.6905 (4)0.45329 (17)0.6941 (6)0.0692 (8)
H100.63950.43770.83200.083*
C80.6355 (4)0.58986 (17)0.7897 (7)0.0730 (8)
H80.58360.57600.92870.088*
C20.8363 (4)0.42221 (19)0.3412 (8)0.0779 (9)
H2A0.88140.38510.24320.093*
C50.7977 (5)0.63455 (19)0.3851 (7)0.0825 (10)
H50.85420.65050.25170.099*
C70.6465 (4)0.66511 (16)0.7296 (7)0.0714 (8)
C10.7519 (4)0.40035 (17)0.5467 (7)0.0716 (8)
C30.8518 (4)0.49797 (18)0.2859 (7)0.0770 (8)
H30.90630.51190.14890.092*
C60.7288 (5)0.68761 (18)0.5269 (8)0.0820 (10)
H60.73630.73930.48920.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0919 (15)0.0691 (13)0.098 (2)0.0024 (10)0.0054 (16)0.0045 (14)
O20.0893 (16)0.0651 (11)0.104 (2)0.0033 (10)0.0120 (15)0.0123 (13)
C40.0736 (17)0.0725 (16)0.069 (2)0.0043 (14)0.0080 (16)0.0034 (17)
C90.0577 (14)0.0686 (17)0.068 (2)0.0010 (11)0.0043 (14)0.0004 (16)
C100.0700 (17)0.0699 (16)0.068 (2)0.0022 (13)0.0010 (16)0.0005 (16)
C80.0779 (18)0.0749 (17)0.0663 (18)0.0025 (14)0.0049 (17)0.0008 (17)
C20.0738 (17)0.0756 (18)0.084 (2)0.0050 (15)0.0018 (19)0.0128 (19)
C50.091 (2)0.080 (2)0.076 (2)0.0107 (16)0.005 (2)0.0110 (19)
C70.0678 (16)0.0653 (16)0.081 (2)0.0045 (13)0.0036 (18)0.0011 (16)
C10.0716 (17)0.0646 (15)0.079 (2)0.0005 (14)0.0049 (17)0.0017 (18)
C30.0769 (18)0.087 (2)0.0674 (19)0.0022 (15)0.0030 (18)0.0034 (19)
C60.091 (2)0.0641 (16)0.091 (3)0.0041 (15)0.000 (2)0.0072 (19)
Geometric parameters (Å, º) top
O1—C11.381 (4)C8—C71.362 (4)
O1—H10.8200C8—H80.9300
O2—C71.390 (4)C2—C31.366 (4)
O2—H20.8200C2—C11.409 (6)
C4—C31.407 (5)C2—H2A0.9300
C4—C51.416 (4)C5—C61.349 (5)
C4—C91.430 (5)C5—H50.9300
C9—C81.408 (4)C7—C61.391 (6)
C9—C101.424 (4)C3—H30.9300
C10—C11.344 (5)C6—H60.9300
C10—H100.9300
C1—O1—H1109.5C1—C2—H2A120.0
C7—O2—H2109.5C6—C5—C4121.9 (4)
C3—C4—C5123.7 (4)C6—C5—H5119.0
C3—C4—C9118.9 (3)C4—C5—H5119.0
C5—C4—C9117.4 (3)C8—C7—C6121.0 (3)
C8—C9—C10122.7 (3)C8—C7—O2121.8 (3)
C8—C9—C4119.1 (3)C6—C7—O2117.2 (3)
C10—C9—C4118.1 (3)C10—C1—O1118.3 (3)
C1—C10—C9121.1 (3)C10—C1—C2120.8 (3)
C1—C10—H10119.5O1—C1—C2120.8 (3)
C9—C10—H10119.5C2—C3—C4121.0 (4)
C7—C8—C9120.4 (3)C2—C3—H3119.5
C7—C8—H8119.8C4—C3—H3119.5
C9—C8—H8119.8C5—C6—C7120.0 (3)
C3—C2—C1120.0 (3)C5—C6—H6120.0
C3—C2—H2A120.0C7—C6—H6120.0
C3—C4—C9—C8179.4 (3)C9—C8—C7—O2177.6 (3)
C5—C4—C9—C80.2 (4)C9—C10—C1—O1174.7 (3)
C3—C4—C9—C101.0 (4)C9—C10—C1—C22.7 (5)
C5—C4—C9—C10179.8 (3)C3—C2—C1—C102.1 (5)
C8—C9—C10—C1178.3 (3)C3—C2—C1—O1175.3 (3)
C4—C9—C10—C12.2 (4)C1—C2—C3—C40.9 (5)
C10—C9—C8—C7178.4 (3)C5—C4—C3—C2179.6 (4)
C4—C9—C8—C72.1 (5)C9—C4—C3—C20.4 (5)
C3—C4—C5—C6177.8 (4)C4—C5—C6—C71.2 (6)
C9—C4—C5—C61.4 (5)C8—C7—C6—C50.7 (5)
C9—C8—C7—C62.4 (5)O2—C7—C6—C5179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.952.714 (3)154
O2—H2···O1ii0.822.112.831 (4)146
Symmetry codes: (i) x+3/2, y1/2, z1/2; (ii) x+1, y+1, z+1/2.
 

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