Redetermination of 1-naphthalenol

In the solid state, the centrosymmetric structure of 1-naphthalenol, C₁₀H₈O, is stabilized by both van der Waals interactions and intermolecular O—H...O hydrogen bonds. The mol­ecules are linked through hydrogen bonds, each of length 2.798 (1) Å, into chains which are parallel to the symmetry axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.112
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       5.82 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: KM4B8 software (Galdecki et al., 1996); cell refinement: KM4B8 software; data reduction: KM4B8 software; program(s) used to solve structure: Please provide missing details; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

1-naphthalenol

Crystal data

C10H8O	F(000) = 304
Mr = 144.16	Dx = 1.282 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.171 (2) Å	θ = 5–20°
b = 4.798 (1) Å	µ = 0.08 mm^−1
c = 13.276 (3) Å	T = 293 K
β = 117.12 (2)°	Columnar, pale white
V = 746.7 (3) Å^3	0.52 × 0.25 × 0.07 mm
Z = 4

Data collection

Kuma KM-4 diffractometer	1197 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
ω–2θ scans	h = −17→17
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	k = −6→6
Tmin = 0.974, Tmax = 0.996	l = −16→16
3416 measured reflections	3 standard reflections every 100 reflections
1708 independent reflections	intensity decay: none

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0217P)^2] where P = (Fo^2 + 2Fc^2)/3
1708 reflections	(Δ/σ)max = 0.001
103 parameters	Δρmax = 0.09 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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
C10	0.30026 (10)	0.0138 (2)	0.27720 (10)	0.0470 (3)
O1	0.46036 (8)	0.2257 (2)	0.27353 (10)	0.0651 (3)
H1	0.4784	0.3686	0.2518	0.098*
C5	0.18092 (11)	−0.0162 (3)	0.22942 (11)	0.0507 (3)
C1	0.34334 (10)	0.2052 (3)	0.22419 (12)	0.0488 (3)
C2	0.27407 (12)	0.3535 (3)	0.13118 (13)	0.0573 (3)
H2	0.3049	0.4766	0.0983	0.069*
C4	0.11065 (11)	0.1426 (3)	0.13223 (12)	0.0599 (4)
H4	0.0318	0.1239	0.1006	0.072*
C3	0.15582 (12)	0.3199 (3)	0.08499 (12)	0.0622 (4)
H3	0.1080	0.4209	0.0210	0.075*
C8	0.32453 (16)	−0.3238 (3)	0.42239 (14)	0.0709 (4)
H8	0.3716	−0.4264	0.4862	0.085*
C9	0.37066 (12)	−0.1449 (3)	0.37505 (12)	0.0574 (3)
H9	0.4495	−0.1258	0.4071	0.069*
C7	0.20626 (16)	−0.3528 (4)	0.37490 (16)	0.0755 (5)
H7	0.1748	−0.4753	0.4073	0.091*
C6	0.13740 (14)	−0.2054 (3)	0.28271 (14)	0.0664 (4)
H6	0.0589	−0.2278	0.2529	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C10	0.0451 (6)	0.0399 (6)	0.0573 (7)	−0.0011 (5)	0.0246 (6)	−0.0113 (5)
O1	0.0420 (5)	0.0540 (6)	0.0989 (8)	−0.0032 (4)	0.0317 (5)	0.0023 (5)
C5	0.0469 (6)	0.0489 (7)	0.0616 (8)	−0.0060 (5)	0.0291 (6)	−0.0154 (6)
C1	0.0394 (6)	0.0420 (6)	0.0670 (8)	−0.0016 (5)	0.0260 (5)	−0.0090 (5)
C2	0.0577 (8)	0.0498 (7)	0.0702 (9)	0.0036 (6)	0.0343 (7)	0.0038 (6)
C4	0.0426 (6)	0.0686 (9)	0.0652 (9)	−0.0012 (6)	0.0217 (6)	−0.0135 (7)
C3	0.0546 (8)	0.0654 (9)	0.0589 (8)	0.0116 (7)	0.0191 (6)	0.0016 (7)
C8	0.0916 (12)	0.0584 (9)	0.0650 (9)	0.0056 (8)	0.0378 (9)	0.0038 (7)
C9	0.0527 (7)	0.0537 (7)	0.0615 (8)	0.0017 (6)	0.0223 (6)	−0.0048 (6)
C7	0.0939 (12)	0.0640 (9)	0.0913 (12)	−0.0115 (8)	0.0619 (11)	−0.0021 (8)
C6	0.0598 (8)	0.0689 (9)	0.0797 (10)	−0.0131 (7)	0.0399 (8)	−0.0118 (8)

Geometric parameters (Å, º)

C10—C5	1.4088 (16)	C4—C3	1.345 (2)
C10—C1	1.4229 (18)	C4—H4	0.9300
C10—C9	1.4245 (19)	C3—H3	0.9300
O1—C1	1.3761 (14)	C8—C9	1.360 (2)
O1—H1	0.8200	C8—C7	1.396 (2)
C5—C4	1.419 (2)	C8—H8	0.9300
C5—C6	1.4222 (19)	C9—H9	0.9300
C1—C2	1.3550 (19)	C7—C6	1.345 (2)
C2—C3	1.399 (2)	C7—H7	0.9300
C2—H2	0.9300	C6—H6	0.9300
C5—C10—C1	117.25 (12)	C4—C3—C2	120.60 (14)
C5—C10—C9	119.00 (12)	C4—C3—H3	119.7
C1—C10—C9	123.75 (12)	C2—C3—H3	119.7
C1—O1—H1	109.5	C9—C8—C7	119.73 (16)
C10—C5—C4	119.06 (13)	C9—C8—H8	120.1
C10—C5—C6	117.47 (13)	C7—C8—H8	120.1
C4—C5—C6	123.47 (13)	C8—C9—C10	121.12 (14)
C2—C1—O1	122.61 (12)	C8—C9—H9	119.4
C2—C1—C10	122.34 (12)	C10—C9—H9	119.4
O1—C1—C10	115.05 (12)	C6—C7—C8	120.63 (15)
C1—C2—C3	119.43 (13)	C6—C7—H7	119.7
C1—C2—H2	120.3	C8—C7—H7	119.7
C3—C2—H2	120.3	C7—C6—C5	122.06 (14)
C3—C4—C5	121.31 (13)	C7—C6—H6	119.0
C3—C4—H4	119.3	C5—C6—H6	119.0
C5—C4—H4	119.3
C1—C10—C5—C4	0.14 (17)	C6—C5—C4—C3	179.76 (13)
C9—C10—C5—C4	179.73 (11)	C5—C4—C3—C2	−0.4 (2)
C1—C10—C5—C6	−179.44 (11)	C1—C2—C3—C4	0.2 (2)
C9—C10—C5—C6	0.15 (17)	C7—C8—C9—C10	−0.2 (2)
C5—C10—C1—C2	−0.34 (18)	C5—C10—C9—C8	0.11 (19)
C9—C10—C1—C2	−179.91 (12)	C1—C10—C9—C8	179.67 (12)
C5—C10—C1—O1	−179.59 (10)	C9—C8—C7—C6	0.0 (2)
C9—C10—C1—O1	0.84 (18)	C8—C7—C6—C5	0.3 (2)
O1—C1—C2—C3	179.39 (12)	C10—C5—C6—C7	−0.3 (2)
C10—C1—C2—C3	0.2 (2)	C4—C5—C6—C7	−179.91 (14)
C10—C5—C4—C3	0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^i	0.82	1.99	2.798 (1)	170

Symmetry code: (i) −x+1, y+1/2, −z+1/2.