The asymmetric unit of the title compound, C
10H
8O
2, contains two planar symmetry-independent molecules linked by an O—H
O hydrogen bond. In the crystal structure, molecules are linked into infinite chains of rings, formed by a combination of O—H
O and C—H
O hydrogen bonds, and additionally reinforced by π–π stacking interactions. Adjacent chains are connected by weak C—H
π interactions.
Supporting information
CCDC reference: 645585
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek,2003) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.
Crystal data top
C10H8O2 | F(000) = 1344 |
Mr = 160.16 | Dx = 1.337 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 15692 reflections |
a = 21.423 (3) Å | θ = 3.8–25.0° |
b = 9.515 (1) Å | µ = 0.09 mm−1 |
c = 15.613 (2) Å | T = 290 K |
V = 3182.6 (7) Å3 | Columnar, brown |
Z = 16 | 0.24 × 0.08 × 0.07 mm |
Data collection top
Oxford Xcalibur3 CCD area-detector diffractometer | 2802 independent reflections |
Radiation source: fine-focus sealed tube | 1924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 25.0°, θmin = 3.8° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005) | h = −25→18 |
Tmin = 0.930, Tmax = 0.998 | k = −11→11 |
15692 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0475P)2 + 1.2166P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
2802 reflections | Δρmax = 0.19 e Å−3 |
238 parameters | Δρmin = −0.15 e Å−3 |
5 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0073 (8) |
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 | x | y | z | Uiso*/Ueq | |
O1A | 0.35502 (7) | −0.21353 (17) | 0.14164 (8) | 0.0589 (4) | |
O2A | 0.34732 (8) | −0.31095 (19) | 0.46165 (8) | 0.0642 (5) | |
C1A | 0.40642 (8) | −0.1434 (2) | 0.17435 (11) | 0.0461 (5) | |
C2A | 0.44611 (10) | −0.0664 (2) | 0.12418 (13) | 0.0588 (6) | |
H2A | 0.4397 | −0.0615 | 0.0653 | 0.071* | |
C3A | 0.49663 (11) | 0.0052 (3) | 0.16159 (15) | 0.0697 (6) | |
H3A | 0.5238 | 0.0564 | 0.1272 | 0.084* | |
C4A | 0.50606 (11) | 0.0003 (2) | 0.24819 (15) | 0.0669 (6) | |
H4A | 0.5393 | 0.0493 | 0.2721 | 0.080* | |
C5A | 0.46584 (9) | −0.0785 (2) | 0.30191 (12) | 0.0513 (5) | |
C6A | 0.47366 (10) | −0.0855 (2) | 0.39218 (13) | 0.0607 (6) | |
H6A | 0.5068 | −0.0378 | 0.4174 | 0.073* | |
C7A | 0.43397 (10) | −0.1602 (2) | 0.44247 (12) | 0.0580 (6) | |
H7A | 0.4397 | −0.1617 | 0.5015 | 0.070* | |
C8A | 0.38416 (9) | −0.2355 (2) | 0.40549 (11) | 0.0483 (5) | |
C9A | 0.37445 (8) | −0.2334 (2) | 0.31847 (11) | 0.0455 (5) | |
H9A | 0.3417 | −0.2843 | 0.2946 | 0.055* | |
C10A | 0.41476 (8) | −0.15295 (19) | 0.26507 (11) | 0.0433 (4) | |
O1B | 0.24927 (7) | −0.03148 (18) | −0.10991 (8) | 0.0624 (4) | |
O2B | 0.25365 (8) | −0.0705 (2) | 0.21477 (8) | 0.0673 (5) | |
C1B | 0.20425 (9) | 0.0632 (2) | −0.08137 (12) | 0.0505 (5) | |
C2B | 0.16820 (10) | 0.1385 (2) | −0.13706 (13) | 0.0610 (6) | |
H2B | 0.1741 | 0.1288 | −0.1958 | 0.073* | |
C3B | 0.12220 (12) | 0.2307 (3) | −0.10581 (15) | 0.0709 (7) | |
H3B | 0.0974 | 0.2808 | −0.1440 | 0.085* | |
C4B | 0.11363 (13) | 0.2472 (3) | −0.01957 (16) | 0.0742 (7) | |
H4B | 0.0833 | 0.3090 | 0.0003 | 0.089* | |
C5B | 0.15053 (10) | 0.1709 (2) | 0.03974 (13) | 0.0575 (5) | |
C6B | 0.14258 (12) | 0.1823 (3) | 0.13046 (15) | 0.0725 (7) | |
H6B | 0.1133 | 0.2450 | 0.1521 | 0.087* | |
C7B | 0.17711 (11) | 0.1032 (3) | 0.18583 (14) | 0.0681 (6) | |
H7B | 0.1710 | 0.1120 | 0.2446 | 0.082* | |
C8B | 0.22162 (10) | 0.0089 (2) | 0.15474 (11) | 0.0533 (5) | |
C9B | 0.23175 (9) | −0.0050 (2) | 0.06820 (12) | 0.0522 (5) | |
C10B | 0.19668 (9) | 0.0754 (2) | 0.00930 (11) | 0.0482 (5) | |
H11A | 0.3546 (10) | −0.209 (2) | 0.0881 (10) | 0.068 (7)* | |
H12A | 0.3189 (11) | −0.356 (3) | 0.4374 (18) | 0.107 (11)* | |
H12B | 0.2832 (10) | −0.115 (3) | 0.1905 (17) | 0.097 (10)* | |
H11B | 0.2467 (11) | −0.039 (3) | −0.1630 (11) | 0.080 (8)* | |
H9B | 0.2607 (9) | −0.074 (2) | 0.0492 (13) | 0.065 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0618 (9) | 0.0865 (11) | 0.0283 (7) | −0.0114 (8) | −0.0032 (6) | −0.0015 (7) |
O2A | 0.0719 (10) | 0.0898 (12) | 0.0309 (7) | −0.0202 (9) | −0.0013 (7) | 0.0030 (7) |
C1A | 0.0478 (10) | 0.0512 (11) | 0.0392 (9) | 0.0010 (9) | 0.0010 (8) | −0.0002 (9) |
C2A | 0.0670 (14) | 0.0637 (13) | 0.0457 (11) | −0.0025 (11) | 0.0054 (10) | 0.0073 (10) |
C3A | 0.0711 (14) | 0.0709 (15) | 0.0670 (15) | −0.0160 (12) | 0.0101 (12) | 0.0142 (12) |
C4A | 0.0637 (14) | 0.0676 (15) | 0.0695 (14) | −0.0190 (12) | −0.0031 (11) | 0.0040 (12) |
C5A | 0.0522 (11) | 0.0516 (12) | 0.0502 (11) | −0.0049 (9) | −0.0044 (9) | −0.0021 (9) |
C6A | 0.0652 (13) | 0.0671 (14) | 0.0499 (12) | −0.0122 (11) | −0.0130 (10) | −0.0060 (10) |
C7A | 0.0715 (14) | 0.0684 (14) | 0.0342 (10) | −0.0074 (11) | −0.0104 (9) | −0.0044 (10) |
C8A | 0.0538 (11) | 0.0582 (12) | 0.0329 (9) | −0.0024 (10) | −0.0004 (8) | −0.0010 (9) |
C9A | 0.0451 (10) | 0.0566 (12) | 0.0346 (9) | −0.0034 (9) | −0.0036 (8) | −0.0029 (8) |
C10A | 0.0475 (10) | 0.0466 (10) | 0.0358 (9) | 0.0025 (8) | −0.0012 (7) | −0.0012 (8) |
O1B | 0.0641 (9) | 0.0951 (12) | 0.0279 (7) | 0.0171 (8) | 0.0005 (6) | −0.0018 (8) |
O2B | 0.0646 (9) | 0.1085 (14) | 0.0287 (7) | 0.0058 (9) | −0.0003 (7) | −0.0030 (8) |
C1B | 0.0515 (11) | 0.0614 (13) | 0.0387 (10) | −0.0015 (10) | 0.0042 (8) | −0.0007 (9) |
C2B | 0.0705 (14) | 0.0698 (14) | 0.0426 (11) | 0.0050 (12) | 0.0035 (10) | 0.0073 (10) |
C3B | 0.0826 (16) | 0.0697 (15) | 0.0603 (14) | 0.0158 (13) | 0.0017 (12) | 0.0139 (12) |
C4B | 0.0871 (17) | 0.0659 (14) | 0.0695 (15) | 0.0229 (13) | 0.0113 (13) | 0.0040 (12) |
C5B | 0.0658 (13) | 0.0576 (13) | 0.0492 (11) | 0.0010 (11) | 0.0086 (10) | −0.0064 (10) |
C6B | 0.0882 (17) | 0.0737 (16) | 0.0557 (13) | 0.0145 (14) | 0.0134 (12) | −0.0126 (12) |
C7B | 0.0828 (16) | 0.0815 (16) | 0.0401 (11) | 0.0015 (13) | 0.0109 (11) | −0.0139 (11) |
C8B | 0.0544 (11) | 0.0720 (14) | 0.0334 (9) | −0.0064 (10) | 0.0009 (8) | −0.0053 (9) |
C9B | 0.0489 (11) | 0.0726 (14) | 0.0352 (10) | 0.0003 (10) | 0.0024 (8) | −0.0047 (10) |
C10B | 0.0505 (11) | 0.0573 (12) | 0.0369 (10) | −0.0067 (9) | 0.0031 (8) | −0.0031 (9) |
Geometric parameters (Å, º) top
O1A—C1A | 1.385 (2) | O1B—C1B | 1.393 (2) |
O1A—H11A | 0.837 (16) | O1B—H11B | 0.834 (16) |
O2A—C8A | 1.381 (2) | O2B—C8B | 1.386 (2) |
O2A—H12A | 0.836 (17) | O2B—H12B | 0.852 (17) |
C1A—C2A | 1.369 (3) | C1B—C2B | 1.366 (3) |
C1A—C10A | 1.430 (2) | C1B—C10B | 1.430 (3) |
C2A—C3A | 1.406 (3) | C2B—C3B | 1.407 (3) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.368 (3) | C3B—C4B | 1.368 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.417 (3) | C4B—C5B | 1.417 (3) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.421 (3) | C5B—C10B | 1.424 (3) |
C5A—C10A | 1.425 (3) | C5B—C6B | 1.431 (3) |
C6A—C7A | 1.358 (3) | C6B—C7B | 1.364 (3) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.409 (3) | C7B—C8B | 1.396 (3) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.375 (2) | C8B—C9B | 1.375 (3) |
C9A—C10A | 1.424 (3) | C9B—C10B | 1.412 (3) |
C9A—H9A | 0.9300 | C9B—H9B | 0.954 (15) |
| | | |
C1A—O1A—H11A | 110.7 (15) | C1B—O1B—H11B | 109.2 (17) |
C8A—O2A—H12A | 113 (2) | C8B—O2B—H12B | 109.8 (19) |
C2A—C1A—O1A | 122.73 (17) | C2B—C1B—O1B | 121.80 (17) |
C2A—C1A—C10A | 121.54 (18) | C2B—C1B—C10B | 121.57 (19) |
O1A—C1A—C10A | 115.71 (16) | O1B—C1B—C10B | 116.62 (17) |
C1A—C2A—C3A | 119.99 (19) | C1B—C2B—C3B | 120.16 (19) |
C1A—C2A—H2A | 120.0 | C1B—C2B—H2B | 119.9 |
C3A—C2A—H2A | 120.0 | C3B—C2B—H2B | 119.9 |
C4A—C3A—C2A | 120.5 (2) | C4B—C3B—C2B | 120.5 (2) |
C4A—C3A—H3A | 119.7 | C4B—C3B—H3B | 119.8 |
C2A—C3A—H3A | 119.7 | C2B—C3B—H3B | 119.8 |
C3A—C4A—C5A | 120.9 (2) | C3B—C4B—C5B | 120.6 (2) |
C3A—C4A—H4A | 119.6 | C3B—C4B—H4B | 119.7 |
C5A—C4A—H4A | 119.6 | C5B—C4B—H4B | 119.7 |
C4A—C5A—C6A | 122.69 (19) | C4B—C5B—C10B | 119.72 (19) |
C4A—C5A—C10A | 119.41 (18) | C4B—C5B—C6B | 122.8 (2) |
C6A—C5A—C10A | 117.90 (18) | C10B—C5B—C6B | 117.5 (2) |
C7A—C6A—C5A | 121.61 (19) | C7B—C6B—C5B | 121.4 (2) |
C7A—C6A—H6A | 119.2 | C7B—C6B—H6B | 119.3 |
C5A—C6A—H6A | 119.2 | C5B—C6B—H6B | 119.3 |
C6A—C7A—C8A | 120.21 (17) | C6B—C7B—C8B | 120.29 (19) |
C6A—C7A—H7A | 119.9 | C6B—C7B—H7B | 119.9 |
C8A—C7A—H7A | 119.9 | C8B—C7B—H7B | 119.9 |
C9A—C8A—O2A | 123.26 (17) | C9B—C8B—O2B | 122.27 (19) |
C9A—C8A—C7A | 120.83 (18) | C9B—C8B—C7B | 120.8 (2) |
O2A—C8A—C7A | 115.91 (16) | O2B—C8B—C7B | 116.96 (17) |
C8A—C9A—C10A | 119.65 (17) | C8B—C9B—C10B | 120.2 (2) |
C8A—C9A—H9A | 120.2 | C8B—C9B—H9B | 118.4 (13) |
C10A—C9A—H9A | 120.2 | C10B—C9B—H9B | 121.2 (13) |
C9A—C10A—C5A | 119.78 (16) | C9B—C10B—C5B | 119.82 (17) |
C9A—C10A—C1A | 122.56 (17) | C9B—C10B—C1B | 122.70 (18) |
C5A—C10A—C1A | 117.66 (17) | C5B—C10B—C1B | 117.45 (18) |
| | | |
O1A—C1A—C2A—C3A | 178.41 (19) | O1B—C1B—C2B—C3B | 178.5 (2) |
C10A—C1A—C2A—C3A | 0.2 (3) | C10B—C1B—C2B—C3B | −0.1 (3) |
C1A—C2A—C3A—C4A | −0.9 (4) | C1B—C2B—C3B—C4B | 0.8 (4) |
C2A—C3A—C4A—C5A | 0.9 (4) | C2B—C3B—C4B—C5B | −0.6 (4) |
C3A—C4A—C5A—C6A | −179.5 (2) | C3B—C4B—C5B—C10B | −0.4 (4) |
C3A—C4A—C5A—C10A | −0.3 (3) | C3B—C4B—C5B—C6B | −178.8 (2) |
C4A—C5A—C6A—C7A | 179.1 (2) | C4B—C5B—C6B—C7B | 177.3 (2) |
C10A—C5A—C6A—C7A | −0.1 (3) | C10B—C5B—C6B—C7B | −1.1 (4) |
C5A—C6A—C7A—C8A | 1.2 (3) | C5B—C6B—C7B—C8B | 0.3 (4) |
C6A—C7A—C8A—C9A | −0.7 (3) | C6B—C7B—C8B—C9B | 0.5 (4) |
C6A—C7A—C8A—O2A | 178.4 (2) | C6B—C7B—C8B—O2B | −178.3 (2) |
O2A—C8A—C9A—C10A | −179.86 (18) | O2B—C8B—C9B—C10B | 178.16 (18) |
C7A—C8A—C9A—C10A | −0.7 (3) | C7B—C8B—C9B—C10B | −0.6 (3) |
C8A—C9A—C10A—C5A | 1.8 (3) | C8B—C9B—C10B—C5B | −0.2 (3) |
C8A—C9A—C10A—C1A | −178.45 (18) | C8B—C9B—C10B—C1B | −178.63 (19) |
C4A—C5A—C10A—C9A | 179.43 (19) | C4B—C5B—C10B—C9B | −177.4 (2) |
C6A—C5A—C10A—C9A | −1.4 (3) | C6B—C5B—C10B—C9B | 1.0 (3) |
C4A—C5A—C10A—C1A | −0.3 (3) | C4B—C5B—C10B—C1B | 1.1 (3) |
C6A—C5A—C10A—C1A | 178.85 (19) | C6B—C5B—C10B—C1B | 179.5 (2) |
C2A—C1A—C10A—C9A | −179.39 (19) | C2B—C1B—C10B—C9B | 177.6 (2) |
O1A—C1A—C10A—C9A | 2.3 (3) | O1B—C1B—C10B—C9B | −1.0 (3) |
C2A—C1A—C10A—C5A | 0.4 (3) | C2B—C1B—C10B—C5B | −0.8 (3) |
O1A—C1A—C10A—C5A | −177.93 (17) | O1B—C1B—C10B—C5B | −179.51 (18) |
Hydrogen-bonding geometry (Å, °) topMotif | D-H···A | D-H | H···A | D···A | D-H···A |
k | O2A-H12A···O1Bi | 0.84 (2) | 1.98 (2) | 2.812 (2) | 175 (3) |
l | O1A-H11A···O2Aii | 0.84 (2) | 1.99 (2) | 2.825 (2) | 175 (2) |
m | O2B-H12B···O1A | 0.85 (2) | 1.96 (2) | 2.806 (2) | 176 (3) |
n | O1B-H11B···O2Biii | 0.83 (2) | 1.93 (2) | 2.763 (2) | 175 (3) |
o | C9B-H9B···O2Aii | 0.95 (2) | 2.55 (2) | 3.459 (3) | 160 (2) |
| C3A-H3A···Cg2iv | 0.93 | 2.95 | 3.634 (3) | 131 |
Symmetry codes: (i) x, -1/2 - y, 1/2 + z; (ii) x, -1/2 - y, -1/2 + z;
(iii) 1/2 - x, y, -1/2 + z; (iv) 1 - x, 1/2 + y, 1/2 - z.
Cg2 is the centroid of the C5A–C10A ring. |
First and second-level graph-set descriptors involving hydrogen bonds
designated k, l, m, n and o top | k | l | m | n | o |
k | D | D33(12) | C22(14) | D33(10) | R22(7) |
l | | C(7) | D33(10) | | D23(10) |
m | | | D | D33(12) | C22(11) |
n | | | | C(7) | D33(12) |
o | | | | | D |