Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704127X/bt2449sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704127X/bt2449Isup2.hkl |
CCDC reference: 660353
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.100
- Data-to-parameter ratio = 21.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C1 - C2 .. 8.70 su
Author Response: check of atomic sites shows these to be assigned correctly, no other reasons for deviation seem valid |
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to standard procedures (Becker et al., 2001) by reaction of dicyclohexylketone and potassium cyanide in acidified water. Recrystallization of the product was performed from chloroform at room temperature upon free evaporation of the solvent.
All H atoms were located in a difference map and refined as riding on their parent atoms. One common isotropic displacement parameter for all H atoms was refined to Uiso(H) = 0.0420 (17).
The title compound, C14H23NO, the cyanohydrin of dicyclohexyl ketone, was prepared as intermediate in the synthesis of α-hydroxy-dicyclohexyl- acetic acid. It was obtained as the product of the acid catalyzed addition of potassium cyanide to dicyclohexylketone.
The cyclohexyl rings adopt chair conformations. The central C atom is in a slightly distorted tetrahedral environment of three C atoms and one O atom. Intramolecular hydrogen bonds are present in the crystal structure.
The molecular structure (Fig. 1) shows two cyclohexane rings, a cyano- and a hydroxy-group attached to one central C atom. The central C atom connects to both rings as equatorial substituent. It is in a slightly distorted tetrahedral environment comprised of C11, C21, C2 and O1.
The molecular packing (Fig. 2) shows intermolecular hydrogen bonds between the O bonded H atom and the N atom of the next molecule.
The title compound was prepared according to standard procedures (Becker et al., 2001).
Data collection: IPDS Software (Stoe & Cie, 1996); cell refinement: IPDS Software (Stoe & Cie, 1996); data reduction: IPDS Software (Stoe & Cie, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C14H23NO | F(000) = 488 |
Mr = 221.34 | Dx = 1.128 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5000 reflections |
a = 10.1300 (11) Å | θ = 2.2–27.9° |
b = 10.8140 (8) Å | µ = 0.07 mm−1 |
c = 12.5540 (13) Å | T = 200 K |
β = 108.548 (12)° | Block, colourless |
V = 1303.8 (2) Å3 | 0.43 × 0.32 × 0.26 mm |
Z = 4 |
Stoe IPDS diffractometer | 3117 independent reflections |
Radiation source: fine-focus sealed tube | 2073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
area detection scans | θmax = 28.0°, θmin = 2.5° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | h = −13→13 |
Tmin = 0.979, Tmax = 0.985 | k = −13→14 |
10944 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3 |
3117 reflections | (Δ/σ)max < 0.001 |
147 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C14H23NO | V = 1303.8 (2) Å3 |
Mr = 221.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.1300 (11) Å | µ = 0.07 mm−1 |
b = 10.8140 (8) Å | T = 200 K |
c = 12.5540 (13) Å | 0.43 × 0.32 × 0.26 mm |
β = 108.548 (12)° |
Stoe IPDS diffractometer | 3117 independent reflections |
Absorption correction: numerical (X-RED; Stoe & Cie, 1997) | 2073 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.985 | Rint = 0.048 |
10944 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.27 e Å−3 |
3117 reflections | Δρmin = −0.17 e Å−3 |
147 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.12139 (9) | 0.76034 (8) | 0.27055 (6) | 0.0276 (2) | |
H1 | 0.1015 | 0.6855 | 0.2747 | 0.0367 (8)* | |
N2 | −0.06931 (12) | 1.00845 (10) | 0.17481 (10) | 0.0342 (3) | |
C1 | 0.06155 (12) | 0.80206 (10) | 0.15801 (9) | 0.0192 (2) | |
C2 | −0.01281 (13) | 0.91914 (11) | 0.16750 (10) | 0.0228 (3) | |
C11 | 0.17886 (12) | 0.83620 (11) | 0.10885 (9) | 0.0220 (3) | |
H11 | 0.1347 | 0.8776 | 0.0348 | 0.0367 (8)* | |
C12 | 0.25527 (13) | 0.72163 (13) | 0.08798 (11) | 0.0311 (3) | |
H121 | 0.2969 | 0.6770 | 0.1597 | 0.0367 (8)* | |
H122 | 0.1881 | 0.6655 | 0.0355 | 0.0367 (8)* | |
C13 | 0.36959 (14) | 0.75672 (16) | 0.03856 (12) | 0.0405 (4) | |
H131 | 0.4206 | 0.6813 | 0.0300 | 0.0367 (8)* | |
H132 | 0.3267 | 0.7931 | −0.0370 | 0.0367 (8)* | |
C14 | 0.47133 (14) | 0.84872 (16) | 0.11226 (13) | 0.0423 (4) | |
H141 | 0.5226 | 0.8091 | 0.1847 | 0.0367 (8)* | |
H142 | 0.5399 | 0.8736 | 0.0750 | 0.0367 (8)* | |
C15 | 0.39607 (14) | 0.96243 (15) | 0.13399 (13) | 0.0390 (3) | |
H151 | 0.3539 | 1.0074 | 0.0625 | 0.0367 (8)* | |
H152 | 0.4638 | 1.0183 | 0.1863 | 0.0367 (8)* | |
C16 | 0.28235 (13) | 0.92723 (13) | 0.18439 (11) | 0.0288 (3) | |
H161 | 0.3256 | 0.8894 | 0.2592 | 0.0367 (8)* | |
H162 | 0.2323 | 1.0027 | 0.1945 | 0.0367 (8)* | |
C21 | −0.04689 (11) | 0.70938 (11) | 0.08676 (9) | 0.0188 (2) | |
H21 | 0.0009 | 0.6275 | 0.0927 | 0.0367 (8)* | |
C22 | −0.10254 (12) | 0.74228 (12) | −0.03845 (9) | 0.0255 (3) | |
H221 | −0.1505 | 0.8233 | −0.0478 | 0.0367 (8)* | |
H222 | −0.0238 | 0.7495 | −0.0687 | 0.0367 (8)* | |
C23 | −0.20376 (13) | 0.64389 (14) | −0.10405 (10) | 0.0317 (3) | |
H231 | −0.2413 | 0.6693 | −0.1838 | 0.0367 (8)* | |
H232 | −0.1531 | 0.5650 | −0.1009 | 0.0367 (8)* | |
C24 | −0.32405 (13) | 0.62365 (14) | −0.05789 (10) | 0.0318 (3) | |
H241 | −0.3834 | 0.5552 | −0.0992 | 0.0367 (8)* | |
H242 | −0.3818 | 0.6994 | −0.0693 | 0.0367 (8)* | |
C25 | −0.26967 (13) | 0.59256 (13) | 0.06700 (10) | 0.0269 (3) | |
H251 | −0.3489 | 0.5856 | 0.0967 | 0.0367 (8)* | |
H252 | −0.2213 | 0.5118 | 0.0775 | 0.0367 (8)* | |
C26 | −0.16947 (12) | 0.69184 (11) | 0.13214 (9) | 0.0221 (3) | |
H261 | −0.1335 | 0.6682 | 0.2124 | 0.0367 (8)* | |
H262 | −0.2201 | 0.7711 | 0.1267 | 0.0367 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0398 (5) | 0.0232 (5) | 0.0157 (4) | −0.0047 (4) | 0.0030 (3) | 0.0033 (3) |
N2 | 0.0388 (6) | 0.0244 (6) | 0.0417 (7) | 0.0030 (5) | 0.0158 (5) | −0.0062 (5) |
C1 | 0.0251 (6) | 0.0181 (6) | 0.0146 (5) | 0.0030 (5) | 0.0066 (4) | 0.0012 (4) |
C2 | 0.0277 (6) | 0.0222 (7) | 0.0213 (6) | −0.0028 (5) | 0.0114 (5) | −0.0019 (5) |
C11 | 0.0218 (6) | 0.0257 (6) | 0.0188 (5) | 0.0016 (5) | 0.0070 (4) | 0.0008 (5) |
C12 | 0.0247 (6) | 0.0341 (8) | 0.0355 (7) | 0.0033 (6) | 0.0111 (5) | −0.0092 (6) |
C13 | 0.0247 (6) | 0.0595 (10) | 0.0403 (8) | 0.0043 (7) | 0.0144 (6) | −0.0111 (7) |
C14 | 0.0224 (7) | 0.0643 (11) | 0.0411 (8) | −0.0023 (7) | 0.0115 (6) | −0.0025 (7) |
C15 | 0.0310 (7) | 0.0469 (9) | 0.0408 (8) | −0.0108 (7) | 0.0137 (6) | −0.0018 (7) |
C16 | 0.0297 (6) | 0.0296 (7) | 0.0277 (6) | −0.0042 (5) | 0.0100 (5) | −0.0024 (5) |
C21 | 0.0218 (5) | 0.0189 (6) | 0.0169 (5) | 0.0025 (5) | 0.0080 (4) | −0.0005 (4) |
C22 | 0.0257 (6) | 0.0352 (7) | 0.0171 (5) | −0.0005 (6) | 0.0088 (5) | 0.0017 (5) |
C23 | 0.0306 (7) | 0.0466 (9) | 0.0179 (6) | −0.0052 (6) | 0.0078 (5) | −0.0041 (6) |
C24 | 0.0266 (6) | 0.0439 (8) | 0.0237 (6) | −0.0067 (6) | 0.0064 (5) | −0.0020 (6) |
C25 | 0.0260 (6) | 0.0317 (7) | 0.0246 (6) | −0.0030 (5) | 0.0103 (5) | −0.0003 (5) |
C26 | 0.0258 (6) | 0.0244 (6) | 0.0184 (5) | 0.0026 (5) | 0.0104 (5) | 0.0011 (5) |
O1—C1 | 1.4220 (13) | C15—H152 | 0.9900 |
O1—H1 | 0.8400 | C16—H161 | 0.9900 |
N2—C2 | 1.1412 (16) | C16—H162 | 0.9900 |
C1—C2 | 1.4972 (16) | C21—C22 | 1.5335 (15) |
C1—C21 | 1.5447 (16) | C21—C26 | 1.5338 (15) |
C1—C11 | 1.5479 (16) | C21—H21 | 1.0000 |
C11—C12 | 1.5271 (17) | C22—C23 | 1.5245 (18) |
C11—C16 | 1.5281 (17) | C22—H221 | 0.9900 |
C11—H11 | 1.0000 | C22—H222 | 0.9900 |
C12—C13 | 1.5255 (18) | C23—C24 | 1.5223 (17) |
C12—H121 | 0.9900 | C23—H231 | 0.9900 |
C12—H122 | 0.9900 | C23—H232 | 0.9900 |
C13—C14 | 1.517 (2) | C24—C25 | 1.5249 (17) |
C13—H131 | 0.9900 | C24—H241 | 0.9900 |
C13—H132 | 0.9900 | C24—H242 | 0.9900 |
C14—C15 | 1.517 (2) | C25—C26 | 1.5242 (17) |
C14—H141 | 0.9900 | C25—H251 | 0.9900 |
C14—H142 | 0.9900 | C25—H252 | 0.9900 |
C15—C16 | 1.5284 (18) | C26—H261 | 0.9900 |
C15—H151 | 0.9900 | C26—H262 | 0.9900 |
C1—O1—H1 | 109.5 | C15—C16—H161 | 109.4 |
O1—C1—C2 | 104.81 (9) | C11—C16—H162 | 109.4 |
O1—C1—C21 | 111.68 (9) | C15—C16—H162 | 109.4 |
C2—C1—C21 | 108.16 (9) | H161—C16—H162 | 108.0 |
O1—C1—C11 | 109.46 (9) | C22—C21—C26 | 109.41 (9) |
C2—C1—C11 | 107.43 (9) | C22—C21—C1 | 113.88 (9) |
C21—C1—C11 | 114.75 (9) | C26—C21—C1 | 112.07 (9) |
N2—C2—C1 | 179.90 (18) | C22—C21—H21 | 107.0 |
C12—C11—C16 | 110.12 (10) | C26—C21—H21 | 107.0 |
C12—C11—C1 | 111.73 (10) | C1—C21—H21 | 107.0 |
C16—C11—C1 | 111.62 (9) | C23—C22—C21 | 110.89 (10) |
C12—C11—H11 | 107.7 | C23—C22—H221 | 109.5 |
C16—C11—H11 | 107.7 | C21—C22—H221 | 109.5 |
C1—C11—H11 | 107.7 | C23—C22—H222 | 109.5 |
C13—C12—C11 | 111.09 (12) | C21—C22—H222 | 109.5 |
C13—C12—H121 | 109.4 | H221—C22—H222 | 108.1 |
C11—C12—H121 | 109.4 | C24—C23—C22 | 112.15 (10) |
C13—C12—H122 | 109.4 | C24—C23—H231 | 109.2 |
C11—C12—H122 | 109.4 | C22—C23—H231 | 109.2 |
H121—C12—H122 | 108.0 | C24—C23—H232 | 109.2 |
C14—C13—C12 | 111.80 (11) | C22—C23—H232 | 109.2 |
C14—C13—H131 | 109.3 | H231—C23—H232 | 107.9 |
C12—C13—H131 | 109.3 | C23—C24—C25 | 110.61 (10) |
C14—C13—H132 | 109.3 | C23—C24—H241 | 109.5 |
C12—C13—H132 | 109.3 | C25—C24—H241 | 109.5 |
H131—C13—H132 | 107.9 | C23—C24—H242 | 109.5 |
C15—C14—C13 | 111.01 (11) | C25—C24—H242 | 109.5 |
C15—C14—H141 | 109.4 | H241—C24—H242 | 108.1 |
C13—C14—H141 | 109.4 | C26—C25—C24 | 110.94 (10) |
C15—C14—H142 | 109.4 | C26—C25—H251 | 109.5 |
C13—C14—H142 | 109.4 | C24—C25—H251 | 109.5 |
H141—C14—H142 | 108.0 | C26—C25—H252 | 109.5 |
C14—C15—C16 | 111.15 (12) | C24—C25—H252 | 109.5 |
C14—C15—H151 | 109.4 | H251—C25—H252 | 108.0 |
C16—C15—H151 | 109.4 | C25—C26—C21 | 111.56 (9) |
C14—C15—H152 | 109.4 | C25—C26—H261 | 109.3 |
C16—C15—H152 | 109.4 | C21—C26—H261 | 109.3 |
H151—C15—H152 | 108.0 | C25—C26—H262 | 109.3 |
C11—C16—C15 | 111.24 (10) | C21—C26—H262 | 109.3 |
C11—C16—H161 | 109.4 | H261—C26—H262 | 108.0 |
O1—C1—C11—C12 | 70.70 (12) | O1—C1—C21—C22 | −173.36 (9) |
C2—C1—C11—C12 | −176.04 (10) | C2—C1—C21—C22 | 71.82 (12) |
C21—C1—C11—C12 | −55.75 (13) | C11—C1—C21—C22 | −48.06 (13) |
O1—C1—C11—C16 | −53.09 (13) | O1—C1—C21—C26 | 61.77 (12) |
C2—C1—C11—C16 | 60.17 (12) | C2—C1—C21—C26 | −53.05 (12) |
C21—C1—C11—C16 | −179.54 (10) | C11—C1—C21—C26 | −172.93 (9) |
C16—C11—C12—C13 | −55.89 (14) | C26—C21—C22—C23 | −56.29 (13) |
C1—C11—C12—C13 | 179.48 (10) | C1—C21—C22—C23 | 177.43 (10) |
C11—C12—C13—C14 | 55.78 (16) | C21—C22—C23—C24 | 56.30 (14) |
C12—C13—C14—C15 | −55.19 (17) | C22—C23—C24—C25 | −55.17 (16) |
C13—C14—C15—C16 | 55.32 (16) | C23—C24—C25—C26 | 55.12 (15) |
C12—C11—C16—C15 | 56.47 (14) | C24—C25—C26—C21 | −57.23 (13) |
C1—C11—C16—C15 | −178.83 (11) | C22—C21—C26—C25 | 57.32 (13) |
C14—C15—C16—C11 | −56.51 (15) | C1—C21—C26—C25 | −175.37 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.84 | 2.07 | 2.8982 (14) | 167 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H23NO |
Mr | 221.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 10.1300 (11), 10.8140 (8), 12.5540 (13) |
β (°) | 108.548 (12) |
V (Å3) | 1303.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.43 × 0.32 × 0.26 |
Data collection | |
Diffractometer | Stoe IPDS |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1997) |
Tmin, Tmax | 0.979, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10944, 3117, 2073 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.100, 0.92 |
No. of reflections | 3117 |
No. of parameters | 147 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.17 |
Computer programs: IPDS Software (Stoe & Cie, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.84 | 2.07 | 2.8982 (14) | 166.6 |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
The title compound, C14H23NO, the cyanohydrin of dicyclohexyl ketone, was prepared as intermediate in the synthesis of α-hydroxy-dicyclohexyl- acetic acid. It was obtained as the product of the acid catalyzed addition of potassium cyanide to dicyclohexylketone.
The cyclohexyl rings adopt chair conformations. The central C atom is in a slightly distorted tetrahedral environment of three C atoms and one O atom. Intramolecular hydrogen bonds are present in the crystal structure.
The molecular structure (Fig. 1) shows two cyclohexane rings, a cyano- and a hydroxy-group attached to one central C atom. The central C atom connects to both rings as equatorial substituent. It is in a slightly distorted tetrahedral environment comprised of C11, C21, C2 and O1.
The molecular packing (Fig. 2) shows intermolecular hydrogen bonds between the O bonded H atom and the N atom of the next molecule.