Naphthalene-1,7-diol

Marciniak, B.

doi:10.1107/S0108270107009109

Naphthalene-1,7-diol

B. Marciniak

The asymmetric unit of the title compound, C₁₀H₈O₂, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107009109/gg3057sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270107009109/gg3057Isup2.hkl Contains datablock I

CCDC reference: 645585

Computing details top

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.

Naphthalene-1,7-diol top

Crystal data top

C₁₀H₈O₂	F(000) = 1344
M_r = 160.16	D_x = 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	R_int = 0.025
ω scans	θ_max = 25.0°, θ_min = 3.8°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005)	h = −25→18
T_min = 0.930, T_max = 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(F_o²) + (0.0475P)² + 1.2166P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2802 reflections	Δρ_max = 0.19 e Å⁻³
238 parameters	Δρ_min = −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	U_iso*/U_eq
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, °) top

Motif	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···Cg2^iv	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

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