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1,8-Dihydroxy­anthraquinone lies on a special position of site symmetry 2; a van der Waals inter­action between the 9-carbonyl O atom of one mol­ecule and the 10-carbonyl O atom of another links adjacent mol­ecules into a linear chain [O...O = 2.779 (3) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025948/hg6225sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025948/hg6225Isup2.hkl
Contains datablock I

CCDC reference: 283928

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.153
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. O3 .. 2.78 Ang.
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C2_a 1.44 Ang. 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 27.00 From the CIF: _reflns_number_total 766 Count of symmetry unique reflns 766 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 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1,8-Dihydroxyanthraquinone top
Crystal data top
C14H8O4Dx = 1.540 Mg m3
Mr = 240.20Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212Cell parameters from 1561 reflections
Hall symbol: P 4abw 2nwθ = 3.6–21.9°
a = 5.7440 (6) ŵ = 0.11 mm1
c = 31.393 (3) ÅT = 295 K
V = 1035.8 (2) Å3Block, red
Z = 40.37 × 0.34 × 0.28 mm
F(000) = 496
Data collection top
Bruker SMART area-detector
diffractometer
509 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 27.0°, θmin = 2.6°
φ and ω scanh = 77
6173 measured reflectionsk = 67
766 independent reflectionsl = 3639
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1067P]
where P = (Fo2 + 2Fc2)/3
766 reflections(Δ/σ)max = 0.001
85 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.14 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5216 (3)0.5216 (3)0.00000.072 (1)
O20.7251 (4)0.3374 (5)0.0632 (1)0.088 (1)
O30.1363 (4)0.1363 (4)0.00000.107 (1)
C10.3680 (5)0.3680 (5)0.00000.051 (1)
C20.3723 (5)0.1863 (5)0.0319 (1)0.051 (1)
C30.5513 (6)0.1810 (6)0.0624 (1)0.068 (1)
C40.5552 (8)0.0069 (8)0.0928 (1)0.091 (1)
C50.3833 (9)0.1567 (8)0.0936 (1)0.099 (2)
C60.2047 (7)0.1555 (6)0.0638 (1)0.085 (1)
C70.1983 (6)0.0143 (5)0.0328 (1)0.063 (1)
C80.0138 (5)0.0138 (5)0.00000.066 (1)
H20.70990.42850.04330.105*
H40.67500.00140.11270.109*
H50.38580.27150.11450.119*
H60.08950.26920.06470.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.073 (1)0.073 (1)0.070 (2)0.032 (2)0.001 (1)0.001 (1)
O20.077 (2)0.113 (2)0.073 (2)0.009 (2)0.018 (1)0.012 (2)
O30.092 (2)0.092 (2)0.137 (3)0.048 (3)0.032 (2)0.032 (2)
C10.054 (1)0.054 (1)0.045 (2)0.011 (2)0.005 (1)0.005 (1)
C20.055 (2)0.055 (2)0.044 (1)0.001 (2)0.007 (1)0.001 (1)
C30.071 (2)0.083 (2)0.049 (2)0.007 (2)0.002 (2)0.001 (2)
C40.093 (3)0.117 (3)0.062 (2)0.028 (3)0.006 (2)0.015 (2)
C50.131 (4)0.092 (3)0.074 (3)0.036 (3)0.035 (3)0.035 (2)
C60.101 (3)0.065 (2)0.089 (3)0.006 (2)0.040 (3)0.015 (2)
C70.070 (2)0.052 (2)0.066 (2)0.005 (2)0.026 (2)0.002 (2)
C80.054 (2)0.054 (2)0.092 (3)0.015 (2)0.019 (2)0.019 (2)
Geometric parameters (Å, º) top
O1—C11.247 (4)C5—C61.389 (6)
O2—C31.344 (4)C6—C71.376 (5)
O3—C81.219 (5)C7—C81.479 (4)
C1—C21.447 (3)C8—C7i1.479 (4)
C1—C2i1.447 (3)O2—H20.8200
C2—C31.405 (4)C4—H40.9300
C2—C71.406 (4)C5—H50.9300
C3—C41.383 (5)C6—H60.9300
C4—C51.363 (5)
O1—C1—C2119.9 (2)C6—C7—C8120.6 (3)
O1—C1—C2i119.9 (2)C2—C7—C8119.8 (3)
C2—C1—C2i120.3 (3)O3—C8—C7i120.6 (2)
C3—C2—C7119.4 (3)O3—C8—C7120.6 (2)
C3—C2—C1120.0 (3)C7—C8—C7i118.9 (4)
C7—C2—C1120.6 (3)C3—O2—H2109.5
O2—C3—C4117.3 (3)C5—C4—H4120.1
O2—C3—C2122.8 (3)C3—C4—H4120.1
C4—C3—C2119.9 (4)C4—C5—H5119.3
C5—C4—C3119.9 (4)C6—C5—H5119.3
C4—C5—C6121.3 (4)C7—C6—H6120.1
C7—C6—C5119.9 (4)C5—C6—H6120.1
C6—C7—C2119.6 (3)
O1—C1—C2—C31.0 (3)C4—C5—C6—C70.4 (6)
C2i—C1—C2—C3179.0 (3)C5—C6—C7—C20.5 (5)
O1—C1—C2—C7178.9 (2)C5—C6—C7—C8178.0 (3)
C2i—C1—C2—C71.1 (2)C3—C2—C7—C60.5 (4)
C7—C2—C3—O2179.1 (3)C1—C2—C7—C6179.4 (2)
C1—C2—C3—O21.0 (4)C3—C2—C7—C8177.9 (2)
C7—C2—C3—C40.3 (4)C1—C2—C7—C82.2 (4)
C1—C2—C3—C4179.8 (3)C6—C7—C8—O30.4 (3)
O2—C3—C4—C5180.0 (3)C2—C7—C8—O3178.9 (2)
C2—C3—C4—C51.1 (5)C6—C7—C8—C7i179.6 (3)
C3—C4—C5—C61.2 (6)C2—C7—C8—C7i1.1 (2)
Symmetry code: (i) y, x, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.821.822.535 (3)145
 

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