7-(Hydroxy­meth­yl)-1a,7b-dihydro-1H-cyclo­propa[a]naphthalene

In the title compound, C₁₂H₁₂O, the cyclopropane ring makes a dihedral angle of 73.1 (2)° with the naphthalene ring system.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.058
• wR factor = 0.168
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         39 Perc.
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.62 Sigma

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Reduction of 1,8-naphthalic anhydride with lithium aluminium hydride has been used by a number of investigators as a source of 1,8-bis-hydroxymethylnaphthalene (Beyler & Sarett, 1952; Bockelheide & Vick, 1956; Trost, 1967; Cason et al., 1973). We attempted to react naphthalene-1,8-dicarboxylic anhydride with lithium aluminium hydride in tetrahydrofuran in one-step to give 1,8-bis-hydroxymethylnaphthalene, but instead compound (I) was obtained. We here report the crystal structure of the title compound, (I).

Bond lengths and angles in (I) are normal (Table 1). The two phenyl rings of naphthalene system are planar. The dihedral angle between the C1–C10 and C7/C8/C11 planes is 73.1 (2)° (Fig. 1).

S2. Experimental

Compound (I) was prepared according to the reported precedure of Popovici-Müller & Spencer (1997). Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from absolute ethanol.

S3. Refinement

The H atoms were placed in calculated positions, with C—H in the range 0.93–0.98 Å, and included in the final cycles of refinement using a riding model. U_iso(H) treatment? Treatment of H atom on O?

Computing details

Data collection: DIFRAC (Gabe et al., 1995); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering.

7-(Hydroxymethyl)-1a,7 b-dihydro-1H-cyclopropa[a]naphthalene

Crystal data

C12H12O	Dx = 1.279 Mg m^−3
Mr = 172.22	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 22 reflections
Hall symbol: -I 4ad	θ = 4.4–7.6°
a = 20.373 (3) Å	µ = 0.08 mm^−1
c = 8.618 (2) Å	T = 292 K
V = 3577.0 (11) Å^3	Block, yellow
Z = 16	0.25 × 0.25 × 0.22 mm
F(000) = 1472

Data collection

Nonius CAD-4 diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 25.2°, θmin = 2.0°
Graphite monochromator	h = 0→24
ω/2θ scans	k = 0→24
1722 measured reflections	l = 0→10
1601 independent reflections	3 standard reflections every 300 reflections
628 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.0786P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
1601 reflections	Δρmax = 0.17 e Å^−3
122 parameters	Δρmin = −0.16 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (8)

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
O1	0.19915 (11)	0.52687 (12)	0.0917 (3)	0.0644 (8)
H0	0.2063	0.5000	0.1605	0.094 (11)*
C1	0.08691 (15)	0.48980 (16)	0.1096 (4)	0.0495 (9)
C2	0.05625 (17)	0.4777 (2)	0.2485 (5)	0.0630 (11)
H2	0.0637	0.5057	0.3320	0.085 (4)*
C3	0.01502 (19)	0.4254 (2)	0.2663 (6)	0.0764 (13)
H3	−0.0051	0.4171	0.3612	0.085 (4)*
C4	0.00383 (17)	0.3853 (2)	0.1411 (6)	0.0692 (13)
H4	−0.0244	0.3497	0.1525	0.085 (4)*
C5	0.0162 (2)	0.3567 (2)	−0.1367 (7)	0.0789 (14)
H5	−0.0133	0.3222	−0.1259	0.094 (11)*
C6	0.0419 (2)	0.3690 (2)	−0.2748 (6)	0.0837 (15)
H6	0.0269	0.3447	−0.3590	0.085 (4)*
C7	0.0916 (2)	0.4174 (2)	−0.3024 (5)	0.0769 (13)
H7	0.0910	0.4392	−0.4038	0.085 (4)*
C8	0.11099 (17)	0.45903 (18)	−0.1648 (4)	0.0590 (10)
H8	0.1220	0.5048	−0.1884	0.085 (4)*
C9	0.07653 (15)	0.44813 (16)	−0.0160 (4)	0.0476 (9)
C10	0.03308 (17)	0.39598 (18)	−0.0012 (5)	0.0571 (10)
C11	0.15706 (19)	0.4093 (2)	−0.2268 (5)	0.0736 (12)
H11A	0.1643	0.3700	−0.1656	0.085 (4)*
H11B	0.1953	0.4249	−0.2828	0.085 (4)*
C12	0.13251 (17)	0.54598 (17)	0.0968 (5)	0.0600 (11)
H12A	0.1222	0.5705	0.0035	0.085 (4)*
H12B	0.1259	0.5749	0.1849	0.085 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0441 (15)	0.0761 (19)	0.073 (2)	−0.0102 (12)	−0.0060 (14)	0.0211 (16)
C1	0.0362 (19)	0.057 (2)	0.056 (2)	0.0070 (17)	−0.0020 (18)	0.007 (2)
C2	0.042 (2)	0.084 (3)	0.062 (3)	0.007 (2)	0.000 (2)	−0.004 (2)
C3	0.044 (2)	0.111 (4)	0.074 (3)	0.000 (2)	0.010 (2)	0.025 (3)
C4	0.044 (2)	0.065 (3)	0.099 (4)	−0.0079 (19)	0.001 (3)	0.031 (3)
C5	0.058 (3)	0.066 (3)	0.112 (4)	−0.001 (2)	−0.014 (3)	−0.006 (3)
C6	0.082 (3)	0.072 (3)	0.097 (4)	0.003 (3)	−0.022 (3)	−0.030 (3)
C7	0.079 (3)	0.084 (3)	0.068 (3)	0.008 (3)	−0.011 (2)	−0.008 (2)
C8	0.068 (3)	0.056 (2)	0.054 (2)	0.005 (2)	−0.008 (2)	0.002 (2)
C9	0.0344 (18)	0.049 (2)	0.059 (3)	0.0082 (16)	−0.0033 (19)	0.0087 (19)
C10	0.045 (2)	0.051 (2)	0.075 (3)	0.0026 (18)	−0.005 (2)	0.007 (2)
C11	0.066 (3)	0.082 (3)	0.072 (3)	0.001 (2)	0.004 (2)	−0.005 (3)
C12	0.054 (2)	0.059 (2)	0.067 (3)	0.0021 (18)	−0.009 (2)	0.002 (2)

Geometric parameters (Å, º)

O1—C12	1.413 (4)	C6—C7	1.433 (6)
O1—H0	0.8200	C6—H6	0.9300
C1—C2	1.373 (5)	C7—C11	1.494 (5)
C1—C9	1.392 (5)	C7—C8	1.510 (5)
C1—C12	1.478 (5)	C7—H7	0.9800
C2—C3	1.366 (5)	C8—C9	1.479 (5)
C2—H2	0.9300	C8—C11	1.481 (5)
C3—C4	1.373 (6)	C8—H8	0.9800
C3—H3	0.9300	C9—C10	1.389 (5)
C4—C10	1.381 (5)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.325 (6)	C12—H12A	0.9700
C5—C10	1.457 (6)	C12—H12B	0.9700
C5—H5	0.9300
C12—O1—H0	109.5	C9—C8—C11	120.7 (3)
C2—C1—C9	120.0 (3)	C9—C8—C7	118.2 (3)
C2—C1—C12	119.3 (4)	C11—C8—C7	59.9 (2)
C9—C1—C12	120.7 (3)	C9—C8—H8	115.5
C3—C2—C1	121.1 (4)	C11—C8—H8	115.5
C3—C2—H2	119.4	C7—C8—H8	115.5
C1—C2—H2	119.4	C10—C9—C1	119.5 (3)
C2—C3—C4	118.6 (4)	C10—C9—C8	119.8 (4)
C2—C3—H3	120.7	C1—C9—C8	120.7 (3)
C4—C3—H3	120.7	C4—C10—C9	118.5 (4)
C3—C4—C10	122.2 (4)	C4—C10—C5	121.5 (4)
C3—C4—H4	118.9	C9—C10—C5	119.9 (4)
C10—C4—H4	118.9	C8—C11—C7	61.0 (3)
C6—C5—C10	121.5 (4)	C8—C11—H11A	117.7
C6—C5—H5	119.2	C7—C11—H11A	117.7
C10—C5—H5	119.2	C8—C11—H11B	117.7
C5—C6—C7	124.0 (4)	C7—C11—H11B	117.7
C5—C6—H6	118.0	H11A—C11—H11B	114.8
C7—C6—H6	118.0	O1—C12—C1	113.1 (3)
C6—C7—C11	118.8 (4)	O1—C12—H12A	109.0
C6—C7—C8	116.2 (4)	C1—C12—H12A	109.0
C11—C7—C8	59.1 (2)	O1—C12—H12B	109.0
C6—C7—H7	116.8	C1—C12—H12B	109.0
C11—C7—H7	116.8	H12A—C12—H12B	107.8
C8—C7—H7	116.8
C9—C1—C2—C3	−0.4 (5)	C7—C8—C9—C10	7.1 (5)
C12—C1—C2—C3	−178.4 (3)	C11—C8—C9—C1	117.4 (4)
C1—C2—C3—C4	−1.0 (5)	C7—C8—C9—C1	−172.6 (3)
C2—C3—C4—C10	0.3 (6)	C3—C4—C10—C9	1.8 (5)
C10—C5—C6—C7	5.1 (6)	C3—C4—C10—C5	−174.3 (3)
C5—C6—C7—C11	63.2 (5)	C1—C9—C10—C4	−3.1 (5)
C5—C6—C7—C8	−4.3 (6)	C8—C9—C10—C4	177.2 (3)
C6—C7—C8—C9	−1.8 (5)	C1—C9—C10—C5	173.0 (3)
C11—C7—C8—C9	−111.1 (4)	C8—C9—C10—C5	−6.7 (5)
C6—C7—C8—C11	109.3 (4)	C6—C5—C10—C4	176.7 (4)
C2—C1—C9—C10	2.5 (5)	C6—C5—C10—C9	0.7 (6)
C12—C1—C9—C10	−179.5 (3)	C9—C8—C11—C7	106.9 (4)
C2—C1—C9—C8	−177.8 (3)	C6—C7—C11—C8	−104.9 (4)
C12—C1—C9—C8	0.2 (5)	C2—C1—C12—O1	106.1 (4)
C11—C8—C9—C10	−62.9 (4)	C9—C1—C12—O1	−71.9 (5)