2-Naphthalenol

In the solid state, the non-centrosymmetric structure of the title compound, C₁₀H₈O, is stabilized both by van der Waals interactions and by O—H...O intermolecular hydrogen bonds. These hydrogen bonds link every mol­ecule with two neighbouring non-equivalent mol­ecules, forming chains. The asymmetric unit contains two mol­ecules, which are related to each other by a pseudo-inversion centre.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.093
• Data-to-parameter ratio = 8.5

checkCIF results

No syntax errors found


 Alert Level B:



PLAT_111  Alert B ADDSYM Detects (Pseudo) Centre of Symmetry ...        100 Perc Fit

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.45
         From the CIF: _reflns_number_total               1744
         Count of symmetry unique reflns         1744
         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
          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.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: DARCH package (Burevestnik, 1991); cell refinement: DARCH package; data reduction: DARCH package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C10H8O	Dx = 1.263 Mg m^−3
Mr = 144.16	Melting point: 123 K
Monoclinic, Cc	Mo Kα radiation, λ = 0.71069 Å
a = 32.074 (6) Å	Cell parameters from 30 reflections
b = 5.931 (1) Å	θ = 1.2–28.0°
c = 8.127 (2) Å	µ = 0.08 mm^−1
β = 101.18 (3)°	T = 293 K
V = 1516.7 (5) Å^3	Needle, pale yellow
Z = 8	0.4 × 0.06 × 0.03 mm
F(000) = 608

Data collection

DARCH-1 diffractometer	1339 reflections with I > 2σ(I)
Radiation source: BSW x-ray tube	Rint = 0.020
Graphite monochromator	θmax = 27.5°, θmin = 1.3°
ω–2θ scans	h = −41→40
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	k = −7→7
Tmin = 0.958, Tmax = 0.998	l = 0→10
1875 measured reflections	3 standard reflections every 120 min
1744 independent reflections	intensity decay: 5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.30	w = 1/[σ^2(Fo^2) + (0.0121P)^2] where P = (Fo^2 + 2Fc^2)/3
1744 reflections	(Δ/σ)max = 0.007
204 parameters	Δρmax = 0.09 e Å^−3
2 restraints	Δρmin = −0.14 e Å^−3

Special details

Experimental. The DIFABS only insignificantly reduced the R value, but it enabled us much better refinement of the structure 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.26010 (9)	0.8581 (4)	0.2004 (4)	0.0870 (7)
H1	0.2586	0.9954	0.2096	0.130*
C1	0.30146 (14)	0.7886 (7)	0.2607 (6)	0.0869 (12)
C2	0.32747 (14)	0.9230 (8)	0.3703 (6)	0.0888 (12)
H2	0.3175	1.0611	0.4005	0.107*
C3	0.36958 (15)	0.8568 (7)	0.4395 (6)	0.0888 (12)
C4	0.39776 (12)	0.9928 (7)	0.5500 (6)	0.0856 (11)
H4	0.3890	1.1339	0.5799	0.103*
C5	0.43793 (15)	0.9203 (7)	0.6142 (6)	0.0896 (11)
H5	0.4554	1.0069	0.6948	0.108*
C6	0.45332 (14)	0.7177 (6)	0.5610 (5)	0.0798 (10)
H6	0.4816	0.6756	0.5966	0.096*
C7	0.42577 (15)	0.5842 (8)	0.4556 (6)	0.0958 (13)
H7	0.4354	0.4440	0.4276	0.115*
C8	0.38384 (14)	0.6449 (7)	0.3867 (5)	0.0857 (11)
C9	0.35595 (17)	0.5133 (9)	0.2751 (7)	0.1030 (14)
H9	0.3651	0.3745	0.2423	0.124*
C10	0.31602 (16)	0.5807 (8)	0.2130 (6)	0.0987 (14)
H10	0.2980	0.4889	0.1381	0.118*
O2	0.22878 (9)	0.2095 (4)	0.3642 (4)	0.0905 (8)
H2A	0.2386	0.3156	0.4240	0.136*
C11	0.18700 (12)	0.2519 (6)	0.2957 (5)	0.0748 (10)
C12	0.16206 (13)	0.1045 (6)	0.1936 (5)	0.0825 (10)
H12	0.1737	−0.0316	0.1676	0.099*
C13	0.11971 (13)	0.1504 (6)	0.1265 (5)	0.0785 (10)
C14	0.09277 (14)	0.0033 (7)	0.0178 (6)	0.0918 (12)
H14	0.1035	−0.1333	−0.0119	0.110*
C15	0.05175 (15)	0.0564 (7)	−0.0441 (6)	0.0911 (12)
H15	0.0346	−0.0455	−0.1133	0.109*
C16	0.03480 (15)	0.2636 (7)	−0.0053 (6)	0.0869 (11)
H16	0.0070	0.3033	−0.0531	0.104*
C17	0.05940 (13)	0.4037 (7)	0.1023 (6)	0.0841 (11)
H17	0.0477	0.5374	0.1323	0.101*
C18	0.10132 (14)	0.3564 (7)	0.1697 (5)	0.0853 (11)
C19	0.12873 (16)	0.5065 (8)	0.2786 (7)	0.1074 (15)
H19	0.1181	0.6439	0.3071	0.129*
C20	0.16999 (15)	0.4536 (8)	0.3416 (6)	0.1001 (14)
H20	0.1869	0.5518	0.4153	0.120*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0912 (17)	0.0816 (14)	0.0892 (18)	0.0035 (13)	0.0202 (14)	0.0036 (15)
C1	0.093 (3)	0.079 (2)	0.090 (3)	0.006 (2)	0.020 (2)	0.003 (2)
C2	0.088 (3)	0.084 (2)	0.097 (3)	0.0010 (19)	0.023 (2)	−0.004 (2)
C3	0.095 (3)	0.085 (2)	0.086 (3)	0.003 (2)	0.017 (3)	0.003 (2)
C4	0.084 (3)	0.085 (2)	0.087 (3)	0.004 (2)	0.016 (2)	−0.001 (2)
C5	0.089 (3)	0.092 (3)	0.087 (3)	−0.002 (2)	0.014 (2)	0.000 (2)
C6	0.076 (2)	0.082 (2)	0.081 (3)	0.0029 (19)	0.014 (2)	−0.001 (2)
C7	0.102 (3)	0.089 (3)	0.100 (3)	0.001 (2)	0.027 (3)	−0.001 (2)
C8	0.082 (3)	0.086 (2)	0.090 (3)	0.002 (2)	0.018 (2)	0.000 (2)
C9	0.112 (3)	0.101 (3)	0.100 (4)	0.000 (3)	0.030 (3)	−0.002 (3)
C10	0.102 (4)	0.094 (3)	0.100 (4)	−0.004 (2)	0.020 (3)	−0.002 (2)
O2	0.0917 (18)	0.0925 (16)	0.0863 (19)	0.0019 (14)	0.0147 (15)	0.0009 (14)
C11	0.071 (2)	0.0766 (19)	0.076 (3)	−0.0046 (16)	0.0133 (19)	−0.0009 (18)
C12	0.085 (3)	0.082 (2)	0.081 (3)	0.0027 (19)	0.017 (2)	0.0001 (19)
C13	0.073 (2)	0.0795 (19)	0.083 (3)	0.0014 (17)	0.014 (2)	0.0001 (19)
C14	0.099 (3)	0.088 (2)	0.089 (3)	0.007 (2)	0.021 (3)	0.001 (2)
C15	0.093 (3)	0.091 (3)	0.090 (3)	0.001 (2)	0.017 (2)	−0.003 (2)
C16	0.087 (3)	0.086 (2)	0.088 (3)	−0.001 (2)	0.017 (2)	0.002 (2)
C17	0.079 (2)	0.088 (2)	0.085 (3)	0.0020 (19)	0.016 (2)	−0.002 (2)
C18	0.091 (3)	0.084 (2)	0.080 (3)	0.000 (2)	0.015 (2)	0.003 (2)
C19	0.104 (3)	0.108 (3)	0.107 (4)	−0.002 (3)	0.014 (3)	−0.007 (3)
C20	0.098 (3)	0.109 (3)	0.092 (3)	0.002 (2)	0.016 (3)	−0.001 (2)

Geometric parameters (Å, º)

O1—C1	1.385 (5)	O2—C11	1.371 (5)
O1—H1	0.820	O2—H2A	0.820
C1—C2	1.355 (6)	C11—C12	1.355 (5)
C1—C10	1.400 (6)	C11—C20	1.395 (6)
C2—C3	1.414 (6)	C12—C13	1.389 (6)
C2—H2	0.930	C12—H12	0.930
C3—C4	1.400 (6)	C13—C14	1.411 (6)
C3—C8	1.432 (5)	C13—C18	1.430 (5)
C4—C5	1.362 (6)	C14—C15	1.351 (6)
C4—H4	0.930	C14—H14	0.930
C5—C6	1.399 (6)	C15—C16	1.405 (6)
C5—H5	0.930	C15—H15	0.930
C6—C7	1.359 (6)	C16—C17	1.345 (6)
C6—H6	0.930	C16—H16	0.930
C7—C8	1.400 (7)	C17—C18	1.379 (6)
C7—H7	0.930	C17—H17	0.930
C8—C9	1.385 (7)	C18—C19	1.431 (6)
C9—C10	1.343 (7)	C19—C20	1.360 (6)
C9—H9	0.930	C19—H19	0.930
C10—H10	0.930	C20—H20	0.930
C1—O1—H1	109.5	C11—O2—H2A	109.5
C2—C1—O1	118.9 (4)	C12—C11—O2	123.0 (3)
C2—C1—C10	120.3 (4)	C12—C11—C20	120.1 (4)
O1—C1—C10	120.8 (4)	O2—C11—C20	116.8 (3)
C1—C2—C3	121.1 (4)	C11—C12—C13	122.0 (4)
C1—C2—H2	119.4	C11—C12—H12	119.0
C3—C2—H2	119.4	C13—C12—H12	119.0
C4—C3—C2	122.9 (4)	C12—C13—C14	123.9 (4)
C4—C3—C8	119.6 (4)	C12—C13—C18	119.3 (4)
C2—C3—C8	117.4 (4)	C14—C13—C18	116.7 (4)
C5—C4—C3	120.6 (4)	C15—C14—C13	121.5 (4)
C5—C4—H4	119.7	C15—C14—H14	119.2
C3—C4—H4	119.7	C13—C14—H14	119.2
C4—C5—C6	121.1 (4)	C14—C15—C16	120.8 (4)
C4—C5—H5	119.4	C14—C15—H15	119.6
C6—C5—H5	119.4	C16—C15—H15	119.6
C7—C6—C5	118.0 (4)	C17—C16—C15	118.9 (5)
C7—C6—H6	121.0	C17—C16—H16	120.6
C5—C6—H6	121.0	C15—C16—H16	120.6
C6—C7—C8	124.0 (4)	C16—C17—C18	122.4 (4)
C6—C7—H7	118.0	C16—C17—H17	118.8
C8—C7—H7	118.0	C18—C17—H17	118.8
C9—C8—C7	124.4 (4)	C17—C18—C13	119.6 (4)
C9—C8—C3	119.2 (4)	C17—C18—C19	123.6 (4)
C7—C8—C3	116.4 (4)	C13—C18—C19	116.8 (4)
C10—C9—C8	121.7 (5)	C20—C19—C18	121.7 (5)
C10—C9—H9	119.1	C20—C19—H19	119.2
C8—C9—H9	119.1	C18—C19—H19	119.2
C9—C10—C1	120.2 (5)	C19—C20—C11	120.0 (5)
C9—C10—H10	119.9	C19—C20—H20	120.0
C1—C10—H10	119.9	C11—C20—H20	120.0
O1—C1—C2—C3	178.1 (4)	O2—C11—C12—C13	179.6 (4)
C10—C1—C2—C3	−0.3 (7)	C20—C11—C12—C13	2.3 (6)
C1—C2—C3—C4	178.5 (5)	C11—C12—C13—C14	179.0 (4)
C1—C2—C3—C8	1.2 (7)	C11—C12—C13—C18	−1.7 (7)
C2—C3—C4—C5	179.5 (4)	C12—C13—C14—C15	−179.9 (4)
C8—C3—C4—C5	−3.3 (7)	C18—C13—C14—C15	0.9 (7)
C3—C4—C5—C6	5.5 (7)	C13—C14—C15—C16	1.6 (7)
C4—C5—C6—C7	−6.3 (7)	C14—C15—C16—C17	−3.6 (7)
C5—C6—C7—C8	5.2 (8)	C15—C16—C17—C18	3.2 (7)
C6—C7—C8—C9	177.8 (5)	C16—C17—C18—C13	−0.7 (7)
C6—C7—C8—C3	−3.1 (7)	C16—C17—C18—C19	177.2 (5)
C4—C3—C8—C9	−178.9 (5)	C12—C13—C18—C17	179.4 (4)
C2—C3—C8—C9	−1.5 (6)	C14—C13—C18—C17	−1.3 (6)
C4—C3—C8—C7	2.0 (6)	C12—C13—C18—C19	1.3 (6)
C2—C3—C8—C7	179.4 (4)	C14—C13—C18—C19	−179.4 (4)
C7—C8—C9—C10	−179.9 (5)	C17—C18—C19—C20	−179.6 (5)
C3—C8—C9—C10	1.0 (8)	C13—C18—C19—C20	−1.6 (7)
C8—C9—C10—C1	−0.1 (8)	C18—C19—C20—C11	2.2 (8)
C2—C1—C10—C9	−0.3 (8)	C12—C11—C20—C19	−2.6 (7)
O1—C1—C10—C9	−178.6 (4)	O2—C11—C20—C19	−179.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	2.14	2.764 (3)	133
O2—H2A···O1^ii	0.82	2.45	2.752 (3)	103

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z+1/2.