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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
CCDC reference: 283928
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C14H8O4 | Dx = 1.540 Mg m−3 |
Mr = 240.20 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 1561 reflections |
Hall symbol: P 4abw 2nw | θ = 3.6–21.9° |
a = 5.7440 (6) Å | µ = 0.11 mm−1 |
c = 31.393 (3) Å | T = 295 K |
V = 1035.8 (2) Å3 | Block, red |
Z = 4 | 0.37 × 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 tube | Rint = 0.048 |
Graphite monochromator | θmax = 27.0°, θmin = 2.6° |
φ and ω scan | h = −7→7 |
6173 measured reflections | k = −6→7 |
766 independent reflections | l = −36→39 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-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 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5216 (3) | 0.5216 (3) | 0.0000 | 0.072 (1) | |
O2 | 0.7251 (4) | 0.3374 (5) | 0.0632 (1) | 0.088 (1) | |
O3 | −0.1363 (4) | −0.1363 (4) | 0.0000 | 0.107 (1) | |
C1 | 0.3680 (5) | 0.3680 (5) | 0.0000 | 0.051 (1) | |
C2 | 0.3723 (5) | 0.1863 (5) | 0.0319 (1) | 0.051 (1) | |
C3 | 0.5513 (6) | 0.1810 (6) | 0.0624 (1) | 0.068 (1) | |
C4 | 0.5552 (8) | 0.0069 (8) | 0.0928 (1) | 0.091 (1) | |
C5 | 0.3833 (9) | −0.1567 (8) | 0.0936 (1) | 0.099 (2) | |
C6 | 0.2047 (7) | −0.1555 (6) | 0.0638 (1) | 0.085 (1) | |
C7 | 0.1983 (6) | 0.0143 (5) | 0.0328 (1) | 0.063 (1) | |
C8 | 0.0138 (5) | 0.0138 (5) | 0.0000 | 0.066 (1) | |
H2 | 0.7099 | 0.4285 | 0.0433 | 0.105* | |
H4 | 0.6750 | 0.0014 | 0.1127 | 0.109* | |
H5 | 0.3858 | −0.2715 | 0.1145 | 0.119* | |
H6 | 0.0895 | −0.2692 | 0.0647 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.073 (1) | 0.073 (1) | 0.070 (2) | −0.032 (2) | −0.001 (1) | 0.001 (1) |
O2 | 0.077 (2) | 0.113 (2) | 0.073 (2) | −0.009 (2) | −0.018 (1) | −0.012 (2) |
O3 | 0.092 (2) | 0.092 (2) | 0.137 (3) | −0.048 (3) | 0.032 (2) | −0.032 (2) |
C1 | 0.054 (1) | 0.054 (1) | 0.045 (2) | −0.011 (2) | 0.005 (1) | −0.005 (1) |
C2 | 0.055 (2) | 0.055 (2) | 0.044 (1) | −0.001 (2) | 0.007 (1) | −0.001 (1) |
C3 | 0.071 (2) | 0.083 (2) | 0.049 (2) | 0.007 (2) | 0.002 (2) | 0.001 (2) |
C4 | 0.093 (3) | 0.117 (3) | 0.062 (2) | 0.028 (3) | 0.006 (2) | 0.015 (2) |
C5 | 0.131 (4) | 0.092 (3) | 0.074 (3) | 0.036 (3) | 0.035 (3) | 0.035 (2) |
C6 | 0.101 (3) | 0.065 (2) | 0.089 (3) | 0.006 (2) | 0.040 (3) | 0.015 (2) |
C7 | 0.070 (2) | 0.052 (2) | 0.066 (2) | −0.005 (2) | 0.026 (2) | −0.002 (2) |
C8 | 0.054 (2) | 0.054 (2) | 0.092 (3) | −0.015 (2) | 0.019 (2) | −0.019 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.247 (4) | C5—C6 | 1.389 (6) |
O2—C3 | 1.344 (4) | C6—C7 | 1.376 (5) |
O3—C8 | 1.219 (5) | C7—C8 | 1.479 (4) |
C1—C2 | 1.447 (3) | C8—C7i | 1.479 (4) |
C1—C2i | 1.447 (3) | O2—H2 | 0.8200 |
C2—C3 | 1.405 (4) | C4—H4 | 0.9300 |
C2—C7 | 1.406 (4) | C5—H5 | 0.9300 |
C3—C4 | 1.383 (5) | C6—H6 | 0.9300 |
C4—C5 | 1.363 (5) | | |
| | | |
O1—C1—C2 | 119.9 (2) | C6—C7—C8 | 120.6 (3) |
O1—C1—C2i | 119.9 (2) | C2—C7—C8 | 119.8 (3) |
C2—C1—C2i | 120.3 (3) | O3—C8—C7i | 120.6 (2) |
C3—C2—C7 | 119.4 (3) | O3—C8—C7 | 120.6 (2) |
C3—C2—C1 | 120.0 (3) | C7—C8—C7i | 118.9 (4) |
C7—C2—C1 | 120.6 (3) | C3—O2—H2 | 109.5 |
O2—C3—C4 | 117.3 (3) | C5—C4—H4 | 120.1 |
O2—C3—C2 | 122.8 (3) | C3—C4—H4 | 120.1 |
C4—C3—C2 | 119.9 (4) | C4—C5—H5 | 119.3 |
C5—C4—C3 | 119.9 (4) | C6—C5—H5 | 119.3 |
C4—C5—C6 | 121.3 (4) | C7—C6—H6 | 120.1 |
C7—C6—C5 | 119.9 (4) | C5—C6—H6 | 120.1 |
C6—C7—C2 | 119.6 (3) | | |
| | | |
O1—C1—C2—C3 | −1.0 (3) | C4—C5—C6—C7 | −0.4 (6) |
C2i—C1—C2—C3 | 179.0 (3) | C5—C6—C7—C2 | −0.5 (5) |
O1—C1—C2—C7 | 178.9 (2) | C5—C6—C7—C8 | 178.0 (3) |
C2i—C1—C2—C7 | −1.1 (2) | C3—C2—C7—C6 | 0.5 (4) |
C7—C2—C3—O2 | 179.1 (3) | C1—C2—C7—C6 | −179.4 (2) |
C1—C2—C3—O2 | −1.0 (4) | C3—C2—C7—C8 | −177.9 (2) |
C7—C2—C3—C4 | 0.3 (4) | C1—C2—C7—C8 | 2.2 (4) |
C1—C2—C3—C4 | −179.8 (3) | C6—C7—C8—O3 | 0.4 (3) |
O2—C3—C4—C5 | −180.0 (3) | C2—C7—C8—O3 | 178.9 (2) |
C2—C3—C4—C5 | −1.1 (5) | C6—C7—C8—C7i | −179.6 (3) |
C3—C4—C5—C6 | 1.2 (6) | C2—C7—C8—C7i | −1.1 (2) |
Symmetry code: (i) y, x, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.82 | 2.535 (3) | 145 |
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