Regiolone from the pericarps of Juglans regia L.

Regiolone [(4RS)-4,8-dihydr­oxy-3,4-dihydro­naphthalen-1(2H)-one], C₁₀H₁₀O₃, isolated from the pericarps of Juglans regia L., is confirmed as a racemate.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.063
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C10     ..       5.82 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C6     -   C7      ..       5.69 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1'    -   C9'     ..       5.18 su
PLAT707_ALERT_1_C D...A   Calc  2.7101(17), Rep    2.713(2), Dev..       1.71 Sigma
              O2'  -O2      1.555   1.555
PLAT707_ALERT_1_C D...A   Calc  2.5661(17), Rep    2.564(2), Dev..       1.24 Sigma
              O3'  -O1'     1.555   1.555

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(4RS)-4,8-Dihydroxy-3,4-dihydronaphthalen-1(2H)-one

Crystal data

C10H10O3	Dx = 1.377 Mg m^−3
Mr = 178.18	Melting point: 366 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.4859 (3) Å	Cell parameters from 1898 reflections
b = 16.6010 (5) Å	θ = 2.5–21.9°
c = 8.7947 (2) Å	µ = 0.10 mm^−1
β = 109.427 (1)°	T = 294 K
V = 1719.16 (8) Å^3	Block, colourless
Z = 8	0.25 × 0.20 × 0.19 mm
F(000) = 752

Data collection

Bruker SMART CCD diffractometer	3207 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→13
Tmin = 0.975, Tmax = 0.981	k = −11→20
9127 measured reflections	l = −10→10

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2)]
S = 1.12	(Δ/σ)max = 0.001
3207 reflections	Δρmax = 0.18 e Å^−3
240 parameters	Δρmin = −0.13 e Å^−3
0 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: 0.0055 (5)

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
C1	1.11903 (16)	0.03247 (11)	0.2624 (2)	0.0494 (5)
C2	1.16782 (14)	0.11003 (10)	0.3375 (2)	0.0600 (6)
H2B	1.2155	0.1318	0.2799	0.072*
H2A	1.2157	0.1001	0.4479	0.072*
C3	1.07816 (14)	0.17265 (11)	0.3376 (2)	0.0582 (6)
H3B	1.1146	0.2194	0.3995	0.070*
H3A	1.0380	0.1899	0.2280	0.070*
C4	0.99501 (14)	0.13682 (10)	0.4105 (2)	0.0489 (5)
H4	1.0382	0.1208	0.5212	0.059*
C5	0.83172 (15)	0.04039 (12)	0.3101 (2)	0.0579 (6)
H5	0.7912	0.0720	0.3594	0.069*
C6	0.78244 (17)	−0.02860 (14)	0.2255 (3)	0.0698 (7)
H6	0.7082	−0.0417	0.2166	0.084*
C7	0.84082 (19)	−0.07753 (12)	0.1550 (2)	0.0679 (6)
H7	0.8066	−0.1233	0.0986	0.082*
C8	0.95137 (18)	−0.05798 (12)	0.1688 (2)	0.0556 (5)
C9	1.00230 (15)	0.01178 (10)	0.2502 (2)	0.0420 (5)
C10	0.94057 (14)	0.06172 (10)	0.3207 (2)	0.0417 (5)
C1'	0.50924 (15)	0.33520 (11)	0.2880 (2)	0.0499 (5)
C2'	0.60406 (15)	0.38816 (10)	0.3844 (2)	0.0553 (5)
H2C	0.5843	0.4116	0.4725	0.066*
H2D	0.6133	0.4319	0.3165	0.066*
C3'	0.71667 (14)	0.34340 (10)	0.4530 (2)	0.0502 (5)
H3D	0.7424	0.3258	0.3658	0.060*
H3C	0.7737	0.3791	0.5222	0.060*
C4'	0.70144 (14)	0.27182 (10)	0.5478 (2)	0.0443 (5)
H4C	0.6716	0.2923	0.6302	0.053*
C5'	0.61961 (14)	0.13352 (10)	0.4644 (2)	0.0487 (5)
H5C	0.6800	0.1116	0.5471	0.058*
C6'	0.53739 (16)	0.08325 (11)	0.3644 (2)	0.0582 (6)
H6C	0.5440	0.0278	0.3800	0.070*
C7'	0.44667 (16)	0.11384 (11)	0.2433 (2)	0.0623 (6)
H7C	0.3922	0.0792	0.1775	0.075*
C8'	0.43592 (15)	0.19604 (12)	0.2186 (2)	0.0542 (5)
C9'	0.51917 (14)	0.24807 (10)	0.3169 (2)	0.0411 (5)
C10'	0.61217 (13)	0.21565 (10)	0.4418 (2)	0.0385 (4)
O1	1.17819 (10)	−0.01389 (8)	0.21361 (16)	0.0727 (4)
O2	0.91278 (11)	0.19482 (8)	0.41893 (14)	0.0598 (4)
H2'	0.8864	0.2176	0.3316	0.090*
O3	1.00584 (12)	−0.10813 (8)	0.09856 (19)	0.0824 (5)
H3'	1.0724	−0.0942	0.1220	0.124*
O1'	0.42507 (10)	0.36507 (7)	0.18597 (16)	0.0723 (4)
O2'	0.80482 (9)	0.23170 (7)	0.63104 (13)	0.0509 (3)
H2E	0.8352	0.2170	0.5663	0.076*
O3'	0.34504 (11)	0.22366 (7)	0.09916 (19)	0.0860 (5)
H3E	0.3475	0.2730	0.0964	0.129*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0455 (13)	0.0557 (14)	0.0466 (13)	0.0101 (11)	0.0150 (10)	0.0083 (10)
C2	0.0400 (12)	0.0630 (15)	0.0796 (16)	−0.0019 (11)	0.0233 (11)	−0.0012 (11)
C3	0.0540 (13)	0.0501 (13)	0.0726 (15)	−0.0037 (10)	0.0237 (12)	−0.0044 (10)
C4	0.0451 (12)	0.0550 (13)	0.0476 (13)	0.0145 (10)	0.0166 (10)	0.0062 (10)
C5	0.0418 (13)	0.0686 (16)	0.0649 (15)	0.0040 (11)	0.0201 (11)	0.0183 (11)
C6	0.0443 (14)	0.0820 (18)	0.0731 (17)	−0.0165 (13)	0.0061 (12)	0.0297 (13)
C7	0.0695 (17)	0.0591 (16)	0.0606 (16)	−0.0156 (13)	0.0021 (13)	0.0098 (11)
C8	0.0626 (15)	0.0513 (14)	0.0475 (14)	0.0018 (12)	0.0110 (12)	0.0037 (10)
C9	0.0419 (12)	0.0434 (12)	0.0389 (12)	0.0030 (9)	0.0111 (10)	0.0070 (9)
C10	0.0366 (11)	0.0482 (12)	0.0389 (12)	0.0036 (9)	0.0107 (9)	0.0115 (9)
C1'	0.0432 (12)	0.0463 (13)	0.0653 (14)	0.0070 (10)	0.0246 (11)	0.0007 (10)
C2'	0.0635 (14)	0.0360 (12)	0.0680 (15)	0.0013 (10)	0.0237 (12)	−0.0058 (9)
C3'	0.0510 (12)	0.0488 (12)	0.0498 (13)	−0.0096 (10)	0.0154 (10)	−0.0056 (9)
C4'	0.0406 (11)	0.0479 (12)	0.0467 (12)	0.0015 (9)	0.0176 (10)	−0.0027 (9)
C5'	0.0478 (12)	0.0441 (13)	0.0560 (13)	0.0038 (10)	0.0196 (10)	0.0068 (9)
C6'	0.0590 (14)	0.0373 (12)	0.0824 (17)	−0.0040 (11)	0.0290 (13)	−0.0006 (11)
C7'	0.0473 (13)	0.0488 (14)	0.0868 (17)	−0.0126 (11)	0.0170 (12)	−0.0135 (11)
C8'	0.0342 (11)	0.0519 (14)	0.0708 (15)	0.0017 (10)	0.0100 (11)	−0.0006 (11)
C9'	0.0347 (11)	0.0361 (11)	0.0559 (13)	0.0002 (9)	0.0195 (10)	−0.0026 (9)
C10'	0.0355 (11)	0.0403 (12)	0.0443 (12)	−0.0003 (9)	0.0194 (9)	−0.0013 (9)
O1	0.0620 (10)	0.0724 (10)	0.0916 (12)	0.0213 (8)	0.0361 (9)	−0.0015 (8)
O2	0.0663 (9)	0.0671 (10)	0.0516 (9)	0.0270 (7)	0.0270 (8)	0.0087 (7)
O3	0.0992 (12)	0.0615 (10)	0.0835 (12)	0.0065 (9)	0.0264 (11)	−0.0178 (8)
O1'	0.0508 (9)	0.0579 (10)	0.0975 (12)	0.0164 (7)	0.0105 (8)	0.0121 (8)
O2'	0.0442 (8)	0.0670 (9)	0.0402 (8)	0.0031 (6)	0.0122 (6)	−0.0032 (6)
O3'	0.0469 (9)	0.0702 (11)	0.1117 (13)	−0.0011 (8)	−0.0127 (9)	0.0009 (9)

Geometric parameters (Å, º)

C1—O1	1.2381 (18)	C1'—C2'	1.492 (2)
C1—C9	1.466 (2)	C2'—C3'	1.526 (2)
C1—C2	1.482 (2)	C2'—H2C	0.970
C2—C3	1.528 (2)	C2'—H2D	0.970
C2—H2B	0.970	C3'—C4'	1.500 (2)
C2—H2A	0.970	C3'—H3D	0.970
C3—C4	1.512 (2)	C3'—H3C	0.970
C3—H3B	0.970	C4'—O2'	1.4202 (17)
C3—H3A	0.970	C4'—C10'	1.513 (2)
C4—O2	1.4275 (17)	C4'—H4C	0.980
C4—C10	1.511 (2)	C5'—C10'	1.3765 (19)
C4—H4	0.980	C5'—C6'	1.387 (2)
C5—C10	1.377 (2)	C5'—H5C	0.930
C5—C6	1.393 (2)	C6'—C7'	1.369 (2)
C5—H5	0.930	C6'—H6C	0.930
C6—C7	1.370 (2)	C7'—C8'	1.381 (2)
C6—H6	0.930	C7'—H7C	0.930
C7—C8	1.383 (2)	C8'—O3'	1.3446 (19)
C7—H7	0.930	C8'—C9'	1.406 (2)
C8—O3	1.348 (2)	C9'—C10'	1.413 (2)
C8—C9	1.398 (2)	O2—H2'	0.820
C9—C10	1.408 (2)	O3—H3'	0.820
C1'—O1'	1.2362 (18)	O2'—H2E	0.820
C1'—C9'	1.467 (2)	O3'—H3E	0.820
O1—C1—C9	121.48 (18)	C9'—C1'—C2'	118.52 (17)
O1—C1—C2	119.35 (17)	C1'—C2'—C3'	112.98 (15)
C9—C1—C2	119.17 (16)	C1'—C2'—H2C	109.0
C1—C2—C3	113.49 (15)	C3'—C2'—H2C	109.0
C1—C2—H2B	108.9	C1'—C2'—H2D	109.0
C3—C2—H2B	108.9	C3'—C2'—H2D	109.0
C1—C2—H2A	108.9	H2C—C2'—H2D	107.8
C3—C2—H2A	108.9	C4'—C3'—C2'	109.59 (14)
H2B—C2—H2A	107.7	C4'—C3'—H3D	109.8
C4—C3—C2	109.82 (15)	C2'—C3'—H3D	109.8
C4—C3—H3B	109.7	C4'—C3'—H3C	109.8
C2—C3—H3B	109.7	C2'—C3'—H3C	109.8
C4—C3—H3A	109.7	H3D—C3'—H3C	108.2
C2—C3—H3A	109.7	O2'—C4'—C3'	113.37 (14)
H3B—C3—H3A	108.2	O2'—C4'—C10'	112.68 (14)
O2—C4—C10	112.18 (14)	C3'—C4'—C10'	110.46 (15)
O2—C4—C3	111.35 (14)	O2'—C4'—H4C	106.6
C10—C4—C3	110.85 (15)	C3'—C4'—H4C	106.6
O2—C4—H4	107.4	C10'—C4'—H4C	106.6
C10—C4—H4	107.4	C10'—C5'—C6'	120.28 (17)
C3—C4—H4	107.4	C10'—C5'—H5C	119.9
C10—C5—C6	119.88 (19)	C6'—C5'—H5C	119.9
C10—C5—H5	120.1	C7'—C6'—C5'	121.12 (18)
C6—C5—H5	120.1	C7'—C6'—H6C	119.4
C7—C6—C5	121.5 (2)	C5'—C6'—H6C	119.4
C7—C6—H6	119.2	C6'—C7'—C8'	120.06 (18)
C5—C6—H6	119.2	C6'—C7'—H7C	120.0
C6—C7—C8	119.1 (2)	C8'—C7'—H7C	120.0
C6—C7—H7	120.4	O3'—C8'—C7'	118.19 (18)
C8—C7—H7	120.4	O3'—C8'—C9'	122.01 (17)
O3—C8—C7	117.09 (19)	C7'—C8'—C9'	119.80 (18)
O3—C8—C9	122.23 (19)	C8'—C9'—C10'	119.50 (16)
C7—C8—C9	120.7 (2)	C8'—C9'—C1'	119.80 (17)
C8—C9—C10	119.37 (18)	C10'—C9'—C1'	120.70 (16)
C8—C9—C1	120.22 (18)	C5'—C10'—C9'	119.21 (16)
C10—C9—C1	120.40 (17)	C5'—C10'—C4'	121.40 (16)
C5—C10—C9	119.41 (17)	C9'—C10'—C4'	119.39 (15)
C5—C10—C4	120.65 (17)	C4—O2—H2'	109.5
C9—C10—C4	119.93 (15)	C8—O3—H3'	109.5
O1'—C1'—C9'	121.58 (17)	C4'—O2'—H2E	109.5
O1'—C1'—C2'	119.90 (17)	C8'—O3'—H3E	109.5
O1—C1—C2—C3	159.61 (17)	O1'—C1'—C2'—C3'	−157.40 (17)
C9—C1—C2—C3	−21.4 (2)	C9'—C1'—C2'—C3'	22.2 (2)
C1—C2—C3—C4	52.4 (2)	C1'—C2'—C3'—C4'	−54.4 (2)
C2—C3—C4—O2	177.46 (14)	C2'—C3'—C4'—O2'	−173.38 (13)
C2—C3—C4—C10	−56.91 (19)	C2'—C3'—C4'—C10'	59.06 (19)
C10—C5—C6—C7	1.7 (3)	C10'—C5'—C6'—C7'	−0.9 (3)
C5—C6—C7—C8	0.2 (3)	C5'—C6'—C7'—C8'	0.2 (3)
C6—C7—C8—O3	179.56 (19)	C6'—C7'—C8'—O3'	−179.43 (18)
C6—C7—C8—C9	−1.5 (3)	C6'—C7'—C8'—C9'	0.8 (3)
O3—C8—C9—C10	179.85 (16)	O3'—C8'—C9'—C10'	179.23 (17)
C7—C8—C9—C10	1.0 (3)	C7'—C8'—C9'—C10'	−1.0 (3)
O3—C8—C9—C1	−0.4 (3)	O3'—C8'—C9'—C1'	−1.3 (3)
C7—C8—C9—C1	−179.23 (16)	C7'—C8'—C9'—C1'	178.45 (16)
O1—C1—C9—C8	−6.0 (3)	O1'—C1'—C9'—C8'	5.1 (3)
C2—C1—C9—C8	175.03 (17)	C2'—C1'—C9'—C8'	−174.53 (16)
O1—C1—C9—C10	173.72 (17)	O1'—C1'—C9'—C10'	−175.42 (17)
C2—C1—C9—C10	−5.2 (2)	C2'—C1'—C9'—C10'	4.9 (2)
C6—C5—C10—C9	−2.2 (3)	C6'—C5'—C10'—C9'	0.7 (2)
C6—C5—C10—C4	179.35 (16)	C6'—C5'—C10'—C4'	−179.22 (16)
C8—C9—C10—C5	0.9 (3)	C8'—C9'—C10'—C5'	0.3 (2)
C1—C9—C10—C5	−178.89 (15)	C1'—C9'—C10'—C5'	−179.21 (14)
C8—C9—C10—C4	179.35 (15)	C8'—C9'—C10'—C4'	−179.81 (15)
C1—C9—C10—C4	−0.4 (2)	C1'—C9'—C10'—C4'	0.7 (2)
O2—C4—C10—C5	−24.3 (2)	O2'—C4'—C10'—C5'	18.7 (2)
C3—C4—C10—C5	−149.45 (15)	C3'—C4'—C10'—C5'	146.65 (15)
O2—C4—C10—C9	157.25 (15)	O2'—C4'—C10'—C9'	−161.21 (14)
C3—C4—C10—C9	32.1 (2)	C3'—C4'—C10'—C9'	−33.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2′···O2′^i	0.82	1.91	2.729 (2)	172
O3—H3′···O1	0.82	1.86	2.581 (2)	146
O2′—H2E···O2	0.82	1.89	2.713 (2)	178
O3′—H3E···O1′	0.82	1.84	2.564 (2)	147

Symmetry code: (i) x, −y+1/2, z−1/2.