(–)-(1R,2S,2′R,5R)-2-(1-Hydro­xyprop-2-yl)-5-methyl­cyclo­hexanol. Corrigendum

Körner, F.; Schürmann, M.; Preut, H.; Kreiser, W.

doi:10.1107/S0108270100005011

addenda and errata

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 56| Part 8| August 2000| Page 1056

doi:10.1107/S0108270100005011

(–)-(1R,2S,2′R,5R)-2-(1-Hydroxyprop-2-yl)-5-methylcyclohexanol. Corrigendum

Ferdinand Körner,^a Markus Schürmann,^a Hans Preut ^a ^* and Wolfgang Kreiser ^a

^aFachbereich Chemie, Universität Dortmund, Otto-Hahn-Straße 6, 44221 Dortmund, Germany
^*Correspondence e-mail: uch002@uxp1.hrz.uni-dortmund.de

(Received 13 March 2000; accepted 2 April 2000)

The crystal structure of the title compound, C₁₀H₂₀O₂, was published [Körner et al. (2000 ). Acta Cryst. C56, 74–75] with an erroneous position for an hydroxy H atom. This has now been corrected and leads to a more sensible hydrogen-bonding scheme.

1. Comment

In the original publication of the crystal structure of the title compound (Körner et al., 2000), an erroneous position for a hydroxyl H atom was reported, which was detected with PLATON (Spek, 2000 ). A new refinement with merged Friedel data (the original analysis was carried out with an unmerged data set), the correct location for the hydroxy H1 atom and the additional introduction of an extinction correction, led to significant improvement in the structural results. Details of the correct hydrogen-bonding scheme are given in Table 1. Molecules are joined in a hydrogen-bonded chain running in the b-axis direction.

2. Experimental

2.1.1. Crystal data

C₁₀H₂₀O₂
M_r = 172.26
Monoclinic, P2₁
a = 8.5710 (7) Å
b = 6.4665 (3) Å
c = 9.8502 (8) Å
β = 106.783 (3)°
V = 522.69 (6) Å³
Z = 2
D_x = 1.095 Mg m⁻³
Mo Kα radiation
Cell parameters from 6694 reflections
θ = 3.73–25.76°
μ = 0.074 mm⁻¹
T = 291 (1) K
Needle, colourless
0.30 × 0.08 × 0.05 mm

2.1.2. Data collection

Nonius KappaCCD diffractometer
Method: 360 frames via ω rotation (Δω = 1°) and two times 60 s per frame
6694 measured reflections
1065 independent reflections
761 reflections with I > 2σ(I)
R_int = 0.022
θ_max = 25.76°
h = −10 → 10
k = −7 → 7
l = −11 → 11

2.1.3. Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.081
S = 1.012
1065 reflections
114 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0457P)² + 0.0006P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.08 e Å⁻³
Δρ_min = −0.10 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.060 (13)

Table 1
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1′ⁱ	0.82	1.84	2.660 (2)	174
O1′—H1′⋯O1ⁱⁱ	0.82	1.90	2.712 (2)	173
Symmetry codes: (i) x, 1 + y, z; (ii) $[1-x,y-{\script{1\over 2}},1-z]$ .

H atoms were treated as riding with distances and displacement parameters set as follows: O—H = 0.82 Å and U_iso(H) = 1.5U_eq(O), Csp—H = 0.98 Å and U_iso(H) = 1.2U_eq(C), Csp²—H = 0.97 Å and U_iso(H) = 1.2U_eq(C), and Csp³—H = 0.96 Å and U_iso(H) = 1.5U_eq(C).

Data collection: KappaCCD Software (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1996 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S0108270100005011/sk1383sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270100005011/sk1383Isup2.hkl

Comment top

In the original publication of the crystal structure of the title compound (Körner et al., 2000), an erroneous position for a hydroxyl H atom was reported, which was detected with PLATON (Spek, 2000). A new refinement with merged Friedel data (the original analysis was carried out with an unmerged data set), the correct location for the hydroxy H1 atom and the additional introduction of an extinction correction, led to significant improvement in the structural results. Details of the correct hydrogen-bonding scheme are in Table 1. Molecules are joined in a hydrogen-bond chain running in the b axis direction.

Experimental top

No Further Text

Computing details top

Data collection: Nonius KappaCCD Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(-)-(1R,2S,2'R,5R)-2-(1-Hydroxyprop-2-yl)-5-methylcyclohexanol top

Crystal data top

C₁₀H₂₀O₂	F(000) = 192
M_r = 172.26	D_x = 1.095 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
a = 8.5710 (7) Å	Cell parameters from 6694 reflections
b = 6.4665 (3) Å	θ = 3.7–25.8°
c = 9.8502 (8) Å	µ = 0.07 mm⁻¹
β = 106.783 (3)°	T = 291 K
V = 522.69 (6) Å³	Needle, colourless
Z = 2	0.30 × 0.08 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	761 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 25.8°, θ_min = 3.7°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −10→10
360 frames via ω–rotation (Δω = 1°) and two times 60 s per frame scans	k = −7→7
6694 measured reflections	l = −11→11
1065 independent reflections

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.081	Calculated w = 1/[σ²(F_o²) + (0.0457P)² + 0.0006P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1065 reflections	Δρ_max = 0.08 e Å⁻³
114 parameters	Δρ_min = −0.10 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (13)

Crystal data top

C₁₀H₂₀O₂	V = 522.69 (6) Å³
M_r = 172.26	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.5710 (7) Å	µ = 0.07 mm⁻¹
b = 6.4665 (3) Å	T = 291 K
c = 9.8502 (8) Å	0.30 × 0.08 × 0.05 mm
β = 106.783 (3)°

Data collection top

Nonius KappaCCD diffractometer	761 reflections with I > 2σ(I)
6694 measured reflections	R_int = 0.022
1065 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.081	H-atom parameters constrained
S = 1.01	Δρ_max = 0.08 e Å⁻³
1065 reflections	Δρ_min = −0.10 e Å⁻³
114 parameters

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
O1	0.40833 (18)	0.3316 (2)	0.35093 (19)	0.0553 (5)
H1	0.4230	0.4567	0.3605	0.083*
O1'	0.4694 (2)	−0.2645 (2)	0.37048 (18)	0.0678 (6)
H1'	0.5129	−0.2297	0.4528	0.102*
C1	0.2434 (2)	0.2922 (3)	0.2694 (2)	0.0450 (6)
H1A	0.2238	0.3614	0.1775	0.054*
C1'	0.4989 (3)	−0.1110 (4)	0.2770 (3)	0.0592 (6)
H1'1	0.5702	−0.1672	0.2256	0.071*
H1'2	0.5534	0.0065	0.3318	0.071*
C2	0.2225 (3)	0.0607 (3)	0.2438 (2)	0.0446 (6)
H2	0.2411	−0.0048	0.3368	0.053*
C2'	0.3418 (3)	−0.0403 (3)	0.1730 (2)	0.0502 (6)
H2'	0.2877	−0.1650	0.1254	0.060*
C3	0.0450 (3)	0.0174 (4)	0.1604 (2)	0.0609 (7)
H3A	0.0236	0.0765	0.0663	0.073*
H3B	0.0292	−0.1309	0.1499	0.073*
C3'	0.3791 (3)	0.0932 (4)	0.0584 (3)	0.0681 (8)
H3'1	0.4409	0.2121	0.1014	0.102*
H3'2	0.2789	0.1373	−0.0079	0.102*
H3'3	0.4410	0.0140	0.0096	0.102*
C4	−0.0768 (3)	0.1050 (4)	0.2310 (3)	0.0659 (8)
H4A	−0.1864	0.0805	0.1704	0.079*
H4B	−0.0651	0.0334	0.3199	0.079*
C5	−0.0529 (3)	0.3352 (4)	0.2594 (3)	0.0601 (7)
H5	−0.0746	0.4055	0.1677	0.072*
C5A	−0.1712 (3)	0.4215 (6)	0.3354 (3)	0.0899 (10)
H5A1	−0.2812	0.3947	0.2795	0.135*
H5A2	−0.1551	0.5680	0.3481	0.135*
H5A3	−0.1516	0.3561	0.4263	0.135*
C6	0.1243 (3)	0.3769 (4)	0.3423 (2)	0.0553 (6)
H6A	0.1406	0.5249	0.3548	0.066*
H6B	0.1465	0.3149	0.4356	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0504 (10)	0.0389 (8)	0.0707 (11)	−0.0058 (7)	0.0085 (8)	−0.0043 (7)
O1'	0.0800 (13)	0.0374 (9)	0.0742 (12)	−0.0061 (8)	0.0038 (10)	0.0021 (8)
C1	0.0415 (13)	0.0419 (13)	0.0489 (13)	−0.0007 (10)	0.0087 (11)	0.0020 (10)
C1'	0.0589 (16)	0.0423 (13)	0.0765 (16)	−0.0006 (11)	0.0199 (13)	−0.0046 (12)
C2	0.0465 (14)	0.0391 (13)	0.0463 (12)	−0.0045 (10)	0.0105 (11)	0.0007 (10)
C2'	0.0532 (15)	0.0404 (13)	0.0562 (14)	−0.0031 (10)	0.0145 (12)	−0.0073 (10)
C3	0.0564 (17)	0.0560 (14)	0.0681 (16)	−0.0105 (12)	0.0146 (14)	−0.0116 (13)
C3'	0.0762 (18)	0.0692 (18)	0.0643 (16)	0.0017 (13)	0.0288 (14)	−0.0007 (13)
C4	0.0457 (15)	0.0751 (18)	0.0748 (17)	−0.0080 (12)	0.0142 (13)	−0.0043 (14)
C5	0.0526 (15)	0.0684 (17)	0.0587 (15)	0.0093 (13)	0.0153 (12)	0.0021 (13)
C5A	0.063 (2)	0.112 (3)	0.098 (2)	0.0151 (17)	0.0303 (17)	−0.014 (2)
C6	0.0590 (15)	0.0466 (14)	0.0590 (14)	0.0036 (11)	0.0150 (12)	−0.0039 (11)

Geometric parameters (Å, º) top

O1—C1	1.433 (3)	C3—H3A	0.9700
O1—H1	0.8200	C3—H3B	0.9700
O1'—C1'	1.425 (3)	C3'—H3'1	0.9600
O1'—H1'	0.8200	C3'—H3'2	0.9600
C1—C6	1.510 (3)	C3'—H3'3	0.9600
C1—C2	1.520 (3)	C4—C5	1.517 (4)
C1—H1A	0.9800	C4—H4A	0.9700
C1'—C2'	1.508 (3)	C4—H4B	0.9700
C1'—H1'1	0.9700	C5—C6	1.527 (3)
C1'—H1'2	0.9700	C5—C5A	1.529 (3)
C2—C3	1.532 (3)	C5—H5	0.9800
C2—C2'	1.539 (3)	C5A—H5A1	0.9600
C2—H2	0.9800	C5A—H5A2	0.9600
C2'—C3'	1.527 (3)	C5A—H5A3	0.9600
C2'—H2'	0.9800	C6—H6A	0.9700
C3—C4	1.521 (3)	C6—H6B	0.9700

C1—O1—H1	109.5	H3A—C3—H3B	107.8
C1'—O1'—H1'	109.5	C2'—C3'—H3'1	109.5
O1—C1—C6	111.23 (18)	C2'—C3'—H3'2	109.5
O1—C1—C2	108.52 (16)	H3'1—C3'—H3'2	109.5
C6—C1—C2	111.91 (19)	C2'—C3'—H3'3	109.5
O1—C1—H1A	108.4	H3'1—C3'—H3'3	109.5
C6—C1—H1A	108.4	H3'2—C3'—H3'3	109.5
C2—C1—H1A	108.4	C5—C4—C3	112.1 (2)
O1'—C1'—C2'	111.09 (18)	C5—C4—H4A	109.2
O1'—C1'—H1'1	109.4	C3—C4—H4A	109.2
C2'—C1'—H1'1	109.4	C5—C4—H4B	109.2
O1'—C1'—H1'2	109.4	C3—C4—H4B	109.2
C2'—C1'—H1'2	109.4	H4A—C4—H4B	107.9
H1'1—C1'—H1'2	108.0	C4—C5—C6	109.4 (2)
C1—C2—C3	108.66 (19)	C4—C5—C5A	112.0 (3)
C1—C2—C2'	115.59 (19)	C6—C5—C5A	111.8 (2)
C3—C2—C2'	111.53 (17)	C4—C5—H5	107.8
C1—C2—H2	106.9	C6—C5—H5	107.8
C3—C2—H2	106.9	C5A—C5—H5	107.8
C2'—C2—H2	106.9	C5—C5A—H5A1	109.5
C1'—C2'—C3'	109.70 (19)	C5—C5A—H5A2	109.5
C1'—C2'—C2	113.63 (18)	H5A1—C5A—H5A2	109.5
C3'—C2'—C2	113.79 (19)	C5—C5A—H5A3	109.5
C1'—C2'—H2'	106.4	H5A1—C5A—H5A3	109.5
C3'—C2'—H2'	106.4	H5A2—C5A—H5A3	109.5
C2—C2'—H2'	106.4	C1—C6—C5	112.73 (18)
C4—C3—C2	113.2 (2)	C1—C6—H6A	109.0
C4—C3—H3A	108.9	C5—C6—H6A	109.0
C2—C3—H3A	108.9	C1—C6—H6B	109.0
C4—C3—H3B	108.9	C5—C6—H6B	109.0
C2—C3—H3B	108.9	H6A—C6—H6B	107.8

O1—C1—C2—C3	178.33 (17)	C1—C2—C3—C4	−54.5 (3)
C6—C1—C2—C3	55.2 (2)	C2'—C2—C3—C4	177.0 (2)
O1—C1—C2—C2'	−55.4 (2)	C2—C3—C4—C5	55.2 (3)
C6—C1—C2—C2'	−178.56 (18)	C3—C4—C5—C6	−53.2 (3)
O1'—C1'—C2'—C3'	−169.72 (18)	C3—C4—C5—C5A	−177.8 (2)
O1'—C1'—C2'—C2	61.7 (2)	O1—C1—C6—C5	−179.2 (2)
C1—C2—C2'—C1'	88.2 (2)	C2—C1—C6—C5	−57.6 (2)
C3—C2—C2'—C1'	−147.1 (2)	C4—C5—C6—C1	55.1 (3)
C1—C2—C2'—C3'	−38.3 (3)	C5A—C5—C6—C1	179.8 (2)
C3—C2—C2'—C3'	86.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1′ⁱ	0.82	1.84	2.660 (2)	174
O1′—H1′···O1ⁱⁱ	0.82	1.90	2.712 (2)	173

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

Experimental details

Crystal data
Chemical formula	C₁₀H₂₀O₂
M_r	172.26
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	8.5710 (7), 6.4665 (3), 9.8502 (8)
β (°)	106.783 (3)
V (Å³)	522.69 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.08 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6694, 1065, 761
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.081, 1.01
No. of reflections	1065
No. of parameters	114
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.10

Computer programs: Nonius KappaCCD Software (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1'ⁱ	0.82	1.84	2.660 (2)	174
O1'—H1'···O1ⁱⁱ	0.82	1.90	2.712 (2)	173

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

References

Körner, F., Schürmann, M., Preut, H. & Kreiser, W. (2000). Acta Cryst. C56, 74–75. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nonius (1998). KappaCCD Software. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1996). Methods Enzymol. 276, 307–326. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2000). PLATON. Utrecht University, The Netherlands. Google Scholar

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STRUCTURAL
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ISSN: 2053-2296

Volume 56| Part 8| August 2000| Page 1056

doi:10.1107/S0108270100005011

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addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(–)-(1R,2S,2′R,5R)-2-(1-Hydro­xyprop-2-yl)-5-methyl­cyclo­hexanol. Corrigendum

1. Comment

2. Experimental

2.1.1. Crystal data

2.1.2. Data collection

2.1.3. Refinement

Supporting information

References

addenda and errata

(–)-(1R,2S,2′R,5R)-2-(1-Hydroxyprop-2-yl)-5-methylcyclohexanol. Corrigendum