Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010702642X/sk3120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010702642X/sk3120Isup2.hkl |
CCDC reference: 655511
The starting material was commercially available naphthalene-1,6-diol (Sigma Aldrich, purity 99%), which was purified by twofold crystallization from anhydrous ethanol. In such purified material, no impurities were detected by gas chromatography. Crystals of (I) were grown from solution in chloroform by slow evaporation of this solvent at a constant temperature of 293 K.
H atoms involved in hydrogen-bond formation (attached to atoms O1A, O2A, O1B, O2B and C9A) were located in a difference Fourier map and refined with isotropic displacement parameters. All O—H distances were restrained with a DFIX 0.83 (3) Å command (Sheldrick, 1997), while the C9A—H9A distance was restrained with a DFIX 0.93 (3) Å command. All other H atoms were included in the refinement at geometrically calculated positions and refined using a riding model with C—H distances of 0.93 Å and with Uiso(H) set at 1.2Ueq(C).
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.
C10H8O2 | F(000) = 672 |
Mr = 160.16 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8646 reflections |
a = 11.5109 (19) Å | θ = 4.4–25.0° |
b = 16.882 (3) Å | µ = 0.10 mm−1 |
c = 7.9362 (19) Å | T = 290 K |
β = 93.034 (17)° | Tablet, red |
V = 1540.1 (5) Å3 | 0.39 × 0.33 × 0.06 mm |
Z = 8 |
Oxford Diffraction Xcalibur3 CCD diffractometer | 2709 independent reflections |
Radiation source: fine-focus sealed tube | 2034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 25.0°, θmin = 4.4° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005) | h = −11→13 |
Tmin = 0.996, Tmax = 0.999 | k = −20→18 |
8646 measured reflections | l = −7→9 |
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)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0617P)2 + 0.0446P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
2709 reflections | Δρmax = 0.15 e Å−3 |
238 parameters | Δρmin = −0.16 e Å−3 |
5 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (2) |
C10H8O2 | V = 1540.1 (5) Å3 |
Mr = 160.16 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.5109 (19) Å | µ = 0.10 mm−1 |
b = 16.882 (3) Å | T = 290 K |
c = 7.9362 (19) Å | 0.39 × 0.33 × 0.06 mm |
β = 93.034 (17)° |
Oxford Diffraction Xcalibur3 CCD diffractometer | 2709 independent reflections |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005) | 2034 reflections with I > 2σ(I) |
Tmin = 0.996, Tmax = 0.999 | Rint = 0.045 |
8646 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 5 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | Δρmax = 0.15 e Å−3 |
2709 reflections | Δρmin = −0.16 e Å−3 |
238 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | −0.03689 (15) | 0.21015 (11) | 0.1858 (2) | 0.0571 (5) | |
H11A | −0.071 (3) | 0.1669 (14) | 0.211 (4) | 0.106 (13)* | |
O2A | 0.11237 (17) | 0.56926 (10) | 0.1928 (2) | 0.0590 (5) | |
H12A | 0.1669 (19) | 0.5703 (17) | 0.129 (3) | 0.069 (9)* | |
C1A | −0.09485 (19) | 0.27314 (14) | 0.2484 (3) | 0.0476 (6) | |
C2A | −0.1980 (2) | 0.26679 (15) | 0.3231 (3) | 0.0538 (6) | |
H2A | −0.2343 | 0.2177 | 0.3289 | 0.065* | |
C3A | −0.2499 (2) | 0.33354 (15) | 0.3912 (3) | 0.0557 (7) | |
H3A | −0.3199 | 0.3283 | 0.4433 | 0.067* | |
C4A | −0.1994 (2) | 0.40556 (16) | 0.3821 (3) | 0.0539 (7) | |
H4A | −0.2344 | 0.4492 | 0.4298 | 0.065* | |
C5A | −0.0938 (2) | 0.41540 (14) | 0.3009 (3) | 0.0457 (6) | |
C6A | −0.0391 (2) | 0.48944 (14) | 0.2871 (3) | 0.0492 (6) | |
H6A | −0.0712 | 0.5339 | 0.3358 | 0.059* | |
C7A | 0.0608 (2) | 0.49652 (13) | 0.2029 (3) | 0.0465 (6) | |
C8A | 0.1097 (2) | 0.43019 (13) | 0.1279 (3) | 0.0477 (6) | |
H8A | 0.1766 | 0.4358 | 0.0681 | 0.057* | |
C9A | 0.0602 (2) | 0.35805 (14) | 0.1420 (3) | 0.0464 (6) | |
H9A | 0.0944 (18) | 0.3128 (11) | 0.093 (2) | 0.045 (6)* | |
C10A | −0.04136 (19) | 0.34851 (13) | 0.2297 (3) | 0.0428 (6) | |
O1B | 0.19124 (16) | 0.19075 (12) | 0.3131 (2) | 0.0639 (5) | |
H11B | 0.1257 (19) | 0.194 (2) | 0.263 (4) | 0.102 (12)* | |
O2B | 0.70072 (16) | 0.07700 (13) | 0.5059 (2) | 0.0710 (6) | |
H12B | 0.709 (3) | 0.0891 (19) | 0.609 (2) | 0.101 (12)* | |
C1B | 0.2706 (2) | 0.16014 (14) | 0.2106 (3) | 0.0481 (6) | |
C2B | 0.2486 (2) | 0.14754 (14) | 0.0447 (3) | 0.0536 (6) | |
H2B | 0.1762 | 0.1600 | −0.0059 | 0.064* | |
C3B | 0.3357 (2) | 0.11558 (17) | −0.0511 (3) | 0.0624 (7) | |
H3B | 0.3204 | 0.1076 | −0.1661 | 0.075* | |
C4B | 0.4411 (2) | 0.09603 (16) | 0.0181 (3) | 0.0597 (7) | |
H4B | 0.4973 | 0.0748 | −0.0487 | 0.072* | |
C5B | 0.4660 (2) | 0.10779 (14) | 0.1909 (3) | 0.0482 (6) | |
C6B | 0.5733 (2) | 0.08620 (15) | 0.2702 (3) | 0.0544 (6) | |
H6B | 0.6299 | 0.0625 | 0.2077 | 0.065* | |
C7B | 0.5945 (2) | 0.09946 (15) | 0.4351 (3) | 0.0535 (6) | |
C8B | 0.5110 (2) | 0.13529 (17) | 0.5319 (3) | 0.0615 (7) | |
H8B | 0.5276 | 0.1451 | 0.6460 | 0.074* | |
C9B | 0.4064 (2) | 0.15570 (15) | 0.4599 (3) | 0.0562 (7) | |
H9B | 0.3512 | 0.1793 | 0.5251 | 0.067* | |
C10B | 0.3801 (2) | 0.14188 (14) | 0.2890 (3) | 0.0457 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0488 (10) | 0.0457 (10) | 0.0766 (12) | 0.0033 (9) | 0.0024 (9) | −0.0062 (9) |
O2A | 0.0595 (12) | 0.0474 (10) | 0.0708 (12) | −0.0086 (9) | 0.0082 (10) | −0.0011 (9) |
C1A | 0.0414 (13) | 0.0486 (14) | 0.0522 (13) | 0.0024 (12) | −0.0035 (11) | 0.0013 (11) |
C2A | 0.0409 (14) | 0.0554 (15) | 0.0647 (15) | −0.0068 (12) | −0.0006 (12) | 0.0060 (13) |
C3A | 0.0453 (15) | 0.0652 (17) | 0.0570 (15) | 0.0021 (13) | 0.0071 (11) | 0.0067 (13) |
C4A | 0.0504 (15) | 0.0587 (16) | 0.0531 (14) | 0.0110 (13) | 0.0073 (11) | −0.0005 (12) |
C5A | 0.0439 (13) | 0.0528 (14) | 0.0398 (12) | 0.0045 (11) | −0.0018 (10) | 0.0028 (10) |
C6A | 0.0533 (15) | 0.0449 (14) | 0.0489 (13) | 0.0045 (12) | 0.0007 (11) | −0.0019 (11) |
C7A | 0.0458 (14) | 0.0446 (14) | 0.0480 (13) | −0.0014 (12) | −0.0071 (11) | 0.0043 (10) |
C8A | 0.0432 (13) | 0.0524 (15) | 0.0472 (13) | 0.0025 (12) | 0.0006 (10) | 0.0029 (11) |
C9A | 0.0447 (14) | 0.0460 (14) | 0.0483 (13) | 0.0043 (12) | 0.0014 (11) | −0.0021 (11) |
C10A | 0.0393 (12) | 0.0488 (13) | 0.0397 (12) | 0.0050 (11) | −0.0036 (9) | 0.0009 (10) |
O1B | 0.0462 (11) | 0.0834 (13) | 0.0619 (11) | 0.0125 (10) | 0.0006 (9) | −0.0043 (10) |
O2B | 0.0475 (11) | 0.1068 (16) | 0.0578 (12) | 0.0135 (10) | −0.0068 (9) | −0.0041 (11) |
C1B | 0.0409 (13) | 0.0508 (14) | 0.0526 (15) | 0.0008 (11) | 0.0034 (11) | 0.0051 (11) |
C2B | 0.0457 (14) | 0.0618 (15) | 0.0523 (15) | −0.0004 (13) | −0.0050 (11) | 0.0064 (12) |
C3B | 0.0623 (17) | 0.0794 (18) | 0.0447 (13) | −0.0072 (15) | −0.0039 (12) | −0.0001 (13) |
C4B | 0.0510 (15) | 0.0811 (19) | 0.0473 (14) | −0.0008 (14) | 0.0055 (12) | −0.0068 (13) |
C5B | 0.0433 (13) | 0.0562 (14) | 0.0451 (13) | −0.0048 (12) | 0.0016 (10) | −0.0001 (11) |
C6B | 0.0408 (13) | 0.0720 (17) | 0.0508 (14) | 0.0035 (12) | 0.0063 (11) | −0.0056 (12) |
C7B | 0.0412 (14) | 0.0672 (16) | 0.0516 (14) | 0.0048 (13) | −0.0010 (11) | 0.0007 (12) |
C8B | 0.0531 (15) | 0.0871 (19) | 0.0439 (14) | 0.0058 (15) | −0.0014 (12) | −0.0050 (13) |
C9B | 0.0492 (14) | 0.0691 (16) | 0.0509 (15) | 0.0099 (13) | 0.0079 (11) | −0.0048 (12) |
C10B | 0.0426 (13) | 0.0497 (14) | 0.0450 (13) | −0.0023 (11) | 0.0021 (10) | 0.0026 (10) |
O1A—C1A | 1.363 (3) | O1B—C1B | 1.357 (3) |
O1A—H11A | 0.86 (2) | O1B—H11B | 0.84 (2) |
O2A—C7A | 1.368 (3) | O2B—C7B | 1.371 (3) |
O2A—H12A | 0.83 (2) | O2B—H12B | 0.84 (2) |
C1A—C2A | 1.359 (3) | C1B—C2B | 1.345 (3) |
C1A—C10A | 1.425 (3) | C1B—C10B | 1.409 (3) |
C2A—C3A | 1.397 (3) | C2B—C3B | 1.398 (4) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.351 (3) | C3B—C4B | 1.346 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.415 (3) | C4B—C5B | 1.400 (3) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.406 (3) | C5B—C6B | 1.405 (3) |
C5A—C10A | 1.412 (3) | C5B—C10B | 1.413 (3) |
C6A—C7A | 1.365 (3) | C6B—C7B | 1.337 (3) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.401 (3) | C7B—C8B | 1.400 (3) |
C8A—C9A | 1.352 (3) | C8B—C9B | 1.350 (3) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.402 (3) | C9B—C10B | 1.394 (3) |
C9A—H9A | 0.95 (2) | C9B—H9B | 0.9300 |
C1A—O1A—H11A | 110 (2) | C1B—O1B—H11B | 111 (2) |
C7A—O2A—H12A | 114 (2) | C7B—O2B—H12B | 112 (2) |
C2A—C1A—O1A | 123.6 (2) | C2B—C1B—O1B | 123.3 (2) |
C2A—C1A—C10A | 120.5 (2) | C2B—C1B—C10B | 121.0 (2) |
O1A—C1A—C10A | 115.9 (2) | O1B—C1B—C10B | 115.7 (2) |
C1A—C2A—C3A | 120.4 (2) | C1B—C2B—C3B | 119.4 (2) |
C1A—C2A—H2A | 119.8 | C1B—C2B—H2B | 120.3 |
C3A—C2A—H2A | 119.8 | C3B—C2B—H2B | 120.3 |
C4A—C3A—C2A | 120.8 (2) | C4B—C3B—C2B | 122.0 (2) |
C4A—C3A—H3A | 119.6 | C4B—C3B—H3B | 119.0 |
C2A—C3A—H3A | 119.6 | C2B—C3B—H3B | 119.0 |
C3A—C4A—C5A | 120.8 (2) | C3B—C4B—C5B | 119.9 (2) |
C3A—C4A—H4A | 119.6 | C3B—C4B—H4B | 120.1 |
C5A—C4A—H4A | 119.6 | C5B—C4B—H4B | 120.1 |
C6A—C5A—C10A | 118.5 (2) | C4B—C5B—C6B | 122.1 (2) |
C6A—C5A—C4A | 122.6 (2) | C4B—C5B—C10B | 119.0 (2) |
C10A—C5A—C4A | 118.9 (2) | C6B—C5B—C10B | 118.9 (2) |
C7A—C6A—C5A | 120.5 (2) | C7B—C6B—C5B | 120.4 (2) |
C7A—C6A—H6A | 119.7 | C7B—C6B—H6B | 119.8 |
C5A—C6A—H6A | 119.7 | C5B—C6B—H6B | 119.8 |
C6A—C7A—O2A | 119.1 (2) | C6B—C7B—O2B | 117.9 (2) |
C6A—C7A—C8A | 120.4 (2) | C6B—C7B—C8B | 121.0 (2) |
O2A—C7A—C8A | 120.5 (2) | O2B—C7B—C8B | 121.2 (2) |
C9A—C8A—C7A | 120.3 (2) | C9B—C8B—C7B | 120.1 (2) |
C9A—C8A—H8A | 119.9 | C9B—C8B—H8B | 120.0 |
C7A—C8A—H8A | 119.9 | C7B—C8B—H8B | 120.0 |
C8A—C9A—C10A | 120.7 (2) | C8B—C9B—C10B | 120.8 (2) |
C8A—C9A—H9A | 120.3 (13) | C8B—C9B—H9B | 119.6 |
C10A—C9A—H9A | 119.0 (13) | C10B—C9B—H9B | 119.6 |
C9A—C10A—C5A | 119.5 (2) | C9B—C10B—C1B | 122.4 (2) |
C9A—C10A—C1A | 122.1 (2) | C9B—C10B—C5B | 118.8 (2) |
C5A—C10A—C1A | 118.4 (2) | C1B—C10B—C5B | 118.8 (2) |
O1A—C1A—C2A—C3A | 177.1 (2) | O1B—C1B—C2B—C3B | −179.9 (2) |
C10A—C1A—C2A—C3A | −3.6 (4) | C10B—C1B—C2B—C3B | 0.2 (4) |
C1A—C2A—C3A—C4A | 0.9 (4) | C1B—C2B—C3B—C4B | 0.8 (4) |
C2A—C3A—C4A—C5A | 1.1 (4) | C2B—C3B—C4B—C5B | −0.1 (4) |
C3A—C4A—C5A—C6A | 179.3 (2) | C3B—C4B—C5B—C6B | 178.0 (2) |
C3A—C4A—C5A—C10A | −0.3 (3) | C3B—C4B—C5B—C10B | −1.4 (4) |
C10A—C5A—C6A—C7A | 1.7 (3) | C4B—C5B—C6B—C7B | 179.0 (2) |
C4A—C5A—C6A—C7A | −177.9 (2) | C10B—C5B—C6B—C7B | −1.5 (4) |
C5A—C6A—C7A—O2A | −179.54 (18) | C5B—C6B—C7B—O2B | 179.9 (2) |
C5A—C6A—C7A—C8A | 0.5 (3) | C5B—C6B—C7B—C8B | −0.3 (4) |
C6A—C7A—C8A—C9A | −1.8 (3) | C6B—C7B—C8B—C9B | 1.2 (4) |
O2A—C7A—C8A—C9A | 178.2 (2) | O2B—C7B—C8B—C9B | −178.9 (2) |
C7A—C8A—C9A—C10A | 0.8 (3) | C7B—C8B—C9B—C10B | −0.3 (4) |
C8A—C9A—C10A—C5A | 1.4 (3) | C8B—C9B—C10B—C1B | 178.0 (2) |
C8A—C9A—C10A—C1A | −179.3 (2) | C8B—C9B—C10B—C5B | −1.5 (4) |
C6A—C5A—C10A—C9A | −2.6 (3) | C2B—C1B—C10B—C9B | 178.7 (2) |
C4A—C5A—C10A—C9A | 177.0 (2) | O1B—C1B—C10B—C9B | −1.2 (3) |
C6A—C5A—C10A—C1A | 178.02 (19) | C2B—C1B—C10B—C5B | −1.8 (4) |
C4A—C5A—C10A—C1A | −2.4 (3) | O1B—C1B—C10B—C5B | 178.3 (2) |
C2A—C1A—C10A—C9A | −175.0 (2) | C4B—C5B—C10B—C9B | −178.1 (2) |
O1A—C1A—C10A—C9A | 4.3 (3) | C6B—C5B—C10B—C9B | 2.4 (3) |
C2A—C1A—C10A—C5A | 4.3 (3) | C4B—C5B—C10B—C1B | 2.4 (3) |
O1A—C1A—C10A—C5A | −176.35 (18) | C6B—C5B—C10B—C1B | −177.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H11A···O2Ai | 0.86 (3) | 1.89 (3) | 2.726 (3) | 165 (3) |
O1B—H11B···O1A | 0.84 (2) | 1.96 (2) | 2.783 (3) | 169 (3) |
O2A—H12A···O2Bii | 0.83 (2) | 1.91 (2) | 2.737 (3) | 176 (2) |
C9A—H9A···O1Biii | 0.95 (2) | 2.54 (2) | 3.191 (3) | 126 (2) |
O2B—H12B···Cg1iv | 0.84 (2) | 2.55 (3) | 3.243 (2) | 140 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H8O2 |
Mr | 160.16 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 290 |
a, b, c (Å) | 11.5109 (19), 16.882 (3), 7.9362 (19) |
β (°) | 93.034 (17) |
V (Å3) | 1540.1 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.39 × 0.33 × 0.06 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur3 CCD diffractometer |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2005) |
Tmin, Tmax | 0.996, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8646, 2709, 2034 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.140, 1.18 |
No. of reflections | 2709 |
No. of parameters | 238 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2005), CrysAlis RED, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek,2003) and DIAMOND (Brandenburg, 2006), SHELXL97.
O1A—C1A | 1.363 (3) | O1B—C1B | 1.357 (3) |
O2A—C7A | 1.368 (3) | O2B—C7B | 1.371 (3) |
C1A—C2A | 1.359 (3) | C1B—C2B | 1.345 (3) |
C1A—C10A | 1.425 (3) | C1B—C10B | 1.409 (3) |
C2A—C3A | 1.397 (3) | C2B—C3B | 1.398 (4) |
C3A—C4A | 1.351 (3) | C3B—C4B | 1.346 (3) |
C4A—C5A | 1.415 (3) | C4B—C5B | 1.400 (3) |
C5A—C6A | 1.406 (3) | C5B—C6B | 1.405 (3) |
C5A—C10A | 1.412 (3) | C5B—C10B | 1.413 (3) |
C6A—C7A | 1.365 (3) | C6B—C7B | 1.337 (3) |
C7A—C8A | 1.401 (3) | C7B—C8B | 1.400 (3) |
C8A—C9A | 1.352 (3) | C8B—C9B | 1.350 (3) |
C9A—C10A | 1.402 (3) | C9B—C10B | 1.394 (3) |
C2A—C1A—O1A | 123.6 (2) | C2B—C1B—O1B | 123.3 (2) |
C2A—C1A—C10A | 120.5 (2) | C2B—C1B—C10B | 121.0 (2) |
O1A—C1A—C10A | 115.9 (2) | O1B—C1B—C10B | 115.7 (2) |
C1A—C2A—C3A | 120.4 (2) | C1B—C2B—C3B | 119.4 (2) |
C4A—C3A—C2A | 120.8 (2) | C4B—C3B—C2B | 122.0 (2) |
C3A—C4A—C5A | 120.8 (2) | C3B—C4B—C5B | 119.9 (2) |
C6A—C5A—C10A | 118.5 (2) | C4B—C5B—C6B | 122.1 (2) |
C6A—C5A—C4A | 122.6 (2) | C4B—C5B—C10B | 119.0 (2) |
C10A—C5A—C4A | 118.9 (2) | C6B—C5B—C10B | 118.9 (2) |
C7A—C6A—C5A | 120.5 (2) | C7B—C6B—C5B | 120.4 (2) |
C6A—C7A—O2A | 119.1 (2) | C6B—C7B—O2B | 117.9 (2) |
C6A—C7A—C8A | 120.4 (2) | C6B—C7B—C8B | 121.0 (2) |
O2A—C7A—C8A | 120.5 (2) | O2B—C7B—C8B | 121.2 (2) |
C9A—C8A—C7A | 120.3 (2) | C9B—C8B—C7B | 120.1 (2) |
C8A—C9A—C10A | 120.7 (2) | C8B—C9B—C10B | 120.8 (2) |
C9A—C10A—C5A | 119.5 (2) | C9B—C10B—C1B | 122.4 (2) |
C9A—C10A—C1A | 122.1 (2) | C9B—C10B—C5B | 118.8 (2) |
C5A—C10A—C1A | 118.4 (2) | C1B—C10B—C5B | 118.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H11A···O2Ai | 0.86 (3) | 1.89 (3) | 2.726 (3) | 165 (3) |
O1B—H11B···O1A | 0.84 (2) | 1.96 (2) | 2.783 (3) | 169 (3) |
O2A—H12A···O2Bii | 0.83 (2) | 1.91 (2) | 2.737 (3) | 176 (2) |
C9A—H9A···O1Biii | 0.95 (2) | 2.54 (2) | 3.191 (3) | 126 (2) |
O2B—H12B···Cg1iv | 0.84 (2) | 2.55 (3) | 3.243 (2) | 140 (3) |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z+1/2. |
This paper is a continuation of our structural studies of mono- and dihydroxynaphthalenes, which are a class of intermediates important for applications in the synthesis of dyes, tanning agents, antioxidants and antiseptics. In the previous papers, the structures of 1-hydroxynaphthalene (1-naphthol; Rozycka-Sokolowska et al., 2004), 2-hydroxynaphthalene (2-naphthol; Marciniak et al., 2003), 1,3-dihydroxynaphthalene (naphthalene-1,3-diol; Marciniak et al., 2006), 1,7-dihydroxynaphthalene (naphthalene-1,7-diol; Marciniak, 2007) and 2,7-dihydroxynaphthalene (naphthalene-2,7-diol; Rozycka-Sokolowska et al., 2005) have been reported, and the results of structural studies of naphthalene-1,6-diol, (I), are presented here.
As in the case of the other naphthalenediol isomers, such as naphthalene-1,7-diol (Marciniak, 2007), naphthalene-2,3-diol and naphthalene-2,6-diol (Belskii et al., 1990), in the structure of the title compound there are two symmetry-independent molecules, A and B, in the asymmetric unit, which are linked by an O—H···O hydrogen bond (Fig. 1 and Table 2). The C—C bond distances range from 1.351 (3) to 1.425 (3) Å in molecule A and 1.337 (3) to 1.413 (3) Å in molecule B (Table 1). In each molecule, four C—C bonds, viz. C1A—C2A, C3A—C4A, C6A—C7A and C8A—C9A, and C1B—C2B, C3B—C4B, C6B—C7B and C8B—C9B, are shorter than the typical aromatic bond length of 1.384 (13) Å (Allen et al., 1987), whereas all the other bonds are longer. The valence angles within the aromatic rings of these molecules lie in the ranges 118.4 (2)–122.6 (2)° and 118.8 (2)–122.4 (2)°, respectively (Table 1). The naphthalene C1A–C10A and C1B–C10B ring systems are practically planar, with largest out-of-plane deviations of 0.049 (2) and -0.027 (2) Å for atoms C1A and C1B, respectively. The O atoms attached to these rings at atoms C1A, C7A, C1B and C7B deviate from the planes of these rings by only 0.130 (2), 0.029 (2), -0.062 (2) and -0.056 (2) Å, respectively. The angle between the mean planes formed by the C atoms of molecules A and B is 81.46 (7)°. This value is in close agreement with that observed for the other naphthalenediol isomer containing two independent molecules, viz. naphthalene-1,7-diol [the dihedral angle between the mean planes formed by the C atoms of the two independent molecules is 78.97 ° (Marciniak, 2007)], and it is about 25° less than the value of this parameter observed for naphthalene-2,3-diol (Belskii et al., 1990). This noncoplanar orientation of two symmetry-independent molecules observed in (I) is in contrast with the nearly coplanar orientation of the independent molecules observed in naphthalene-2,6-diol [the dihedral angle between the mean planes formed by the C atoms of the two independent molecules is 4.6 (4)° (Belskii et al., 1990)].
Apart from the above-mentioned O1B—H11B···O1A hydrogen bond, in the crystal structure of (I), there are also two intermolecular O—H···O hydrogen bonds and one intermolecular C—H···O hydrogen bond (Table 2 and Figs. 2–4). The O1A—H11A···O2Ai interactions [symmetry code: (i) -x, y - 1/2, -z + 1/2] link the A molecules into a C(8) chain (Bernstein et al., 1995) running parallel to the [010] direction (Fig. 2). The A molecules belonging to the C(8) chains are connected to B molecules by two O—H···O hydrogen bonds, viz. O1B—H11B···O1A and O2A—H12A···O2Bii [symmetry code: (ii) -x + 1, y + 1/2, -z + 1/2], which are classified as D on the first-level graph set (Bernstein et al., 1995). The combined effect of these three O—H···O hydrogen bonds is the formation of a puckered sheet parallel to the (001) plane containing R66(36) rings (Fig. 2). The non-H atoms belonging to the (001) sheets lie in the domains (-0.05 + z/2) < c < (0.55 + z/2) (where z is zero or an integer). Moreover, each such sheet is linked to two neighbouring sheets by a classical O—H···π hydrogen bond and a weak C—H···O hydrogen bond to form a continuous three-dimensional network (Fig. 4). Atom O2B in molecule B at (x, y, z), belonging to the sheet in domain -0.05 < c < 0.55, acts as a hydrogen-bond donor, via atom H12B, to the C1A–C5A/C10A benzene ring (centroid Cg1) of molecule A at (1 + x, 1/2 - y, 1/2 + z), which belongs to the adjacent sheet in domain 0.45 < c < 1.05. As mentioned above, in the structure of (I) there is also a C—H···O interaction, which links atom C9A atom of molecule A at (x, y, z), via H9A, with atom O1B at (x, -y + 1/2, z - 1/2), and this can be described by the graph-set notation D (Fig. 2 and Table 1). A detailed analysis of the three-dimensional network indicates that, apart from the above-mentioned R66(36) rings, this network contains also R66(18) and R66(30) rings formed by the combined effect of the O1B—H11B···O1A, O1A—H11A···O2Ai and C9A—H9A···O1Biii hydrogen bonds (Fig. 3), as well as R44(26) rings, being a combination of the C9A—H9A···O1Biii and O2A—H12A···O2Bii hydrogen bonds [symmetry code: (iii) x, -y + 1/2, z - 1/2] (Fig. 4).