The title compound, C
19H
26O
3, was synthesized from (1
R,2
S,5
R)-2-isopropyl-5-methylcyclohexyl chloroacetate and benzaldehyde
via the well known Darzen reaction. The absolute configuration was determined from the synthetic precursor. Non-classical C—H
O hydrogen bonds link the molecules in the crystal structure into a sheet parallel to (001).
Supporting information
CCDC reference: 270449
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.123
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O2 .. 2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. O2 .. 2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. O1 .. 2.69 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.23
From the CIF: _reflns_number_total 2312
Count of symmetry unique reflns 2315
Completeness (_total/calc) 99.87%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
(1
R,2S,5
R)-2-Isopropyl-5-methylcyclohexyl
(2
S,3S)-3-phenyloxirane-2-carboxylate
top
Crystal data top
C19H26O3 | Dx = 1.132 Mg m−3 |
Mr = 302.4 | Melting point: 104 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 17363 reflections |
a = 5.6507 (6) Å | θ = 1.8–27.3° |
b = 12.8745 (17) Å | µ = 0.08 mm−1 |
c = 24.386 (3) Å | T = 293 K |
V = 1774.1 (4) Å3 | Prism, colorless |
Z = 4 | 0.7 × 0.38 × 0.23 mm |
F(000) = 656 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.054 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.2°, θmin = 2.3° |
ω scans | h = −7→7 |
14189 measured reflections | k = −16→16 |
2312 independent reflections | l = −31→30 |
1675 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0636P)2 + 0.1274P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.047 | (Δ/σ)max < 0.001 |
wR(F2) = 0.124 | Δρmax = 0.13 e Å−3 |
S = 1.02 | Δρmin = −0.12 e Å−3 |
2312 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
203 parameters | Extinction coefficient: 0.023 (3) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.3969 (4) | 0.35533 (17) | 0.13176 (9) | 0.0557 (5) | |
C2 | 0.1558 (4) | 0.3274 (2) | 0.15209 (10) | 0.0637 (6) | |
H2 | 0.0293 | 0.3241 | 0.1246 | 0.076* | |
C3 | 0.0868 (4) | 0.35831 (18) | 0.20759 (10) | 0.0637 (6) | |
H3 | −0.0826 | 0.3716 | 0.2126 | 0.076* | |
C4 | 0.2445 (4) | 0.41691 (19) | 0.24467 (9) | 0.0575 (6) | |
C5 | 0.1872 (5) | 0.5177 (2) | 0.25721 (11) | 0.0709 (7) | |
H5 | 0.0486 | 0.5465 | 0.2434 | 0.085* | |
C6 | 0.3327 (6) | 0.5764 (2) | 0.28993 (12) | 0.0835 (8) | |
H6 | 0.2927 | 0.6449 | 0.2978 | 0.1* | |
C7 | 0.5348 (6) | 0.5352 (3) | 0.31091 (12) | 0.0860 (9) | |
H7 | 0.6336 | 0.5756 | 0.3327 | 0.103* | |
C8 | 0.5923 (5) | 0.4348 (3) | 0.29991 (11) | 0.0809 (8) | |
H8 | 0.729 | 0.4061 | 0.3148 | 0.097* | |
C9 | 0.4476 (5) | 0.3751 (2) | 0.26649 (10) | 0.0682 (7) | |
H9 | 0.488 | 0.3066 | 0.2588 | 0.082* | |
C10 | 0.6001 (4) | 0.48769 (19) | 0.08178 (9) | 0.0614 (6) | |
H10 | 0.7271 | 0.4359 | 0.0827 | 0.074* | |
C11 | 0.6610 (5) | 0.5744 (2) | 0.12059 (10) | 0.0731 (7) | |
H11A | 0.6819 | 0.5463 | 0.1572 | 0.088* | |
H11B | 0.531 | 0.6235 | 0.1218 | 0.088* | |
C12 | 0.8851 (6) | 0.6306 (2) | 0.10349 (12) | 0.0791 (8) | |
H12 | 1.0157 | 0.5806 | 0.1043 | 0.095* | |
C13 | 0.9468 (9) | 0.7197 (3) | 0.14215 (16) | 0.1204 (14) | |
H13A | 0.8207 | 0.7697 | 0.1421 | 0.181* | |
H13B | 1.0904 | 0.7523 | 0.1301 | 0.181* | |
H13C | 0.9681 | 0.6931 | 0.1786 | 0.181* | |
C14 | 0.8575 (7) | 0.6683 (2) | 0.04544 (13) | 0.0941 (10) | |
H14A | 1.0048 | 0.6997 | 0.0334 | 0.113* | |
H14B | 0.7357 | 0.7214 | 0.0442 | 0.113* | |
C15 | 0.7922 (7) | 0.5817 (3) | 0.00672 (12) | 0.0923 (10) | |
H15A | 0.9224 | 0.5327 | 0.0049 | 0.111* | |
H15B | 0.7699 | 0.6103 | −0.0297 | 0.111* | |
C16 | 0.5665 (5) | 0.5234 (2) | 0.02368 (10) | 0.0721 (7) | |
H16 | 0.4376 | 0.5743 | 0.0239 | 0.087* | |
C17 | 0.4926 (7) | 0.4362 (3) | −0.01516 (12) | 0.0962 (10) | |
H17 | 0.3534 | 0.4031 | 0.0012 | 0.115* | |
C18 | 0.6787 (10) | 0.3521 (3) | −0.02126 (18) | 0.1379 (17) | |
H18A | 0.6191 | 0.2979 | −0.0445 | 0.207* | |
H18B | 0.7159 | 0.3239 | 0.0142 | 0.207* | |
H18C | 0.819 | 0.3812 | −0.0373 | 0.207* | |
C19 | 0.4147 (9) | 0.4786 (5) | −0.07110 (14) | 0.1505 (19) | |
H19A | 0.5507 | 0.5026 | −0.091 | 0.226* | |
H19B | 0.3064 | 0.5352 | −0.0658 | 0.226* | |
H19C | 0.338 | 0.4244 | −0.0915 | 0.226* | |
O1 | 0.1465 (3) | 0.25354 (13) | 0.19492 (7) | 0.0766 (5) | |
O2 | 0.5762 (3) | 0.31145 (14) | 0.14234 (8) | 0.0746 (5) | |
O3 | 0.3811 (3) | 0.43912 (14) | 0.10025 (7) | 0.0669 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0517 (12) | 0.0571 (13) | 0.0583 (12) | 0.0017 (11) | −0.0036 (11) | −0.0044 (10) |
C2 | 0.0514 (12) | 0.0688 (15) | 0.0711 (14) | −0.0071 (11) | −0.0041 (12) | −0.0038 (12) |
C3 | 0.0488 (12) | 0.0634 (14) | 0.0788 (15) | −0.0097 (11) | 0.0078 (12) | 0.0002 (12) |
C4 | 0.0506 (12) | 0.0640 (14) | 0.0578 (12) | −0.0049 (11) | 0.0091 (11) | 0.0056 (11) |
C5 | 0.0686 (16) | 0.0659 (15) | 0.0782 (15) | 0.0039 (13) | 0.0028 (14) | 0.0016 (14) |
C6 | 0.095 (2) | 0.0670 (17) | 0.0885 (18) | −0.0022 (16) | 0.0067 (18) | −0.0126 (15) |
C7 | 0.089 (2) | 0.093 (2) | 0.0757 (17) | −0.0174 (18) | 0.0018 (17) | −0.0166 (15) |
C8 | 0.0650 (16) | 0.105 (2) | 0.0721 (15) | 0.0016 (16) | −0.0079 (15) | −0.0010 (16) |
C9 | 0.0633 (16) | 0.0691 (15) | 0.0722 (15) | 0.0055 (13) | 0.0077 (13) | 0.0005 (13) |
C10 | 0.0507 (12) | 0.0629 (14) | 0.0707 (13) | 0.0102 (11) | 0.0087 (12) | 0.0094 (11) |
C11 | 0.0759 (17) | 0.0716 (16) | 0.0719 (14) | 0.0067 (14) | 0.0003 (14) | 0.0076 (14) |
C12 | 0.0737 (17) | 0.0639 (15) | 0.0997 (19) | −0.0004 (14) | −0.0012 (17) | 0.0060 (14) |
C13 | 0.138 (3) | 0.082 (2) | 0.140 (3) | −0.021 (2) | −0.016 (3) | −0.009 (2) |
C14 | 0.098 (2) | 0.0778 (19) | 0.107 (2) | −0.0112 (18) | 0.017 (2) | 0.0148 (17) |
C15 | 0.099 (2) | 0.099 (2) | 0.0793 (18) | −0.0008 (19) | 0.0260 (17) | 0.0148 (17) |
C16 | 0.0714 (17) | 0.0784 (16) | 0.0666 (14) | 0.0123 (14) | 0.0097 (14) | 0.0085 (13) |
C17 | 0.099 (2) | 0.115 (2) | 0.0740 (17) | −0.003 (2) | 0.0060 (18) | −0.0069 (19) |
C18 | 0.163 (4) | 0.117 (3) | 0.134 (3) | 0.015 (3) | 0.008 (3) | −0.056 (3) |
C19 | 0.166 (4) | 0.214 (5) | 0.0722 (19) | −0.005 (5) | −0.006 (3) | 0.000 (3) |
O1 | 0.0745 (11) | 0.0586 (10) | 0.0967 (12) | −0.0197 (9) | 0.0095 (11) | 0.0020 (9) |
O2 | 0.0546 (10) | 0.0720 (11) | 0.0972 (13) | 0.0066 (9) | 0.0022 (9) | 0.0199 (10) |
O3 | 0.0499 (9) | 0.0732 (11) | 0.0776 (10) | 0.0087 (8) | 0.0049 (9) | 0.0144 (9) |
Geometric parameters (Å, º) top
C1—O2 | 1.188 (3) | C11—H11A | 0.97 |
C1—O3 | 1.328 (3) | C11—H11B | 0.97 |
C1—C2 | 1.494 (3) | C12—C14 | 1.505 (4) |
C2—O1 | 1.413 (3) | C12—C13 | 1.525 (4) |
C2—C3 | 1.464 (3) | C12—H12 | 0.98 |
C2—H2 | 0.98 | C13—H13A | 0.96 |
C3—O1 | 1.424 (3) | C13—H13B | 0.96 |
C3—C4 | 1.477 (3) | C13—H13C | 0.96 |
C3—H3 | 0.98 | C14—C15 | 1.507 (4) |
C4—C5 | 1.372 (4) | C14—H14A | 0.97 |
C4—C9 | 1.375 (4) | C14—H14B | 0.97 |
C5—C6 | 1.372 (4) | C15—C16 | 1.536 (4) |
C5—H5 | 0.93 | C15—H15A | 0.97 |
C6—C7 | 1.360 (4) | C15—H15B | 0.97 |
C6—H6 | 0.93 | C16—C17 | 1.527 (4) |
C7—C8 | 1.359 (4) | C16—H16 | 0.98 |
C7—H7 | 0.93 | C17—C18 | 1.517 (5) |
C8—C9 | 1.387 (4) | C17—C19 | 1.534 (5) |
C8—H8 | 0.93 | C17—H17 | 0.98 |
C9—H9 | 0.93 | C18—H18A | 0.96 |
C10—O3 | 1.458 (3) | C18—H18B | 0.96 |
C10—C16 | 1.501 (3) | C18—H18C | 0.96 |
C10—C11 | 1.504 (4) | C19—H19A | 0.96 |
C10—H10 | 0.98 | C19—H19B | 0.96 |
C11—C12 | 1.517 (4) | C19—H19C | 0.96 |
| | | |
O2—C1—O3 | 124.7 (2) | C14—C12—H12 | 108 |
O2—C1—C2 | 126.2 (2) | C11—C12—H12 | 108 |
O3—C1—C2 | 109.0 (2) | C13—C12—H12 | 108 |
O1—C2—C3 | 59.32 (15) | C12—C13—H13A | 109.5 |
O1—C2—C1 | 116.2 (2) | C12—C13—H13B | 109.5 |
C3—C2—C1 | 119.0 (2) | H13A—C13—H13B | 109.5 |
O1—C2—H2 | 116.7 | C12—C13—H13C | 109.5 |
C3—C2—H2 | 116.7 | H13A—C13—H13C | 109.5 |
C1—C2—H2 | 116.7 | H13B—C13—H13C | 109.5 |
O1—C3—C2 | 58.59 (16) | C12—C14—C15 | 112.1 (2) |
O1—C3—C4 | 118.3 (2) | C12—C14—H14A | 109.2 |
C2—C3—C4 | 123.0 (2) | C15—C14—H14A | 109.2 |
O1—C3—H3 | 115.1 | C12—C14—H14B | 109.2 |
C2—C3—H3 | 115.1 | C15—C14—H14B | 109.2 |
C4—C3—H3 | 115.1 | H14A—C14—H14B | 107.9 |
C5—C4—C9 | 118.7 (2) | C14—C15—C16 | 113.3 (3) |
C5—C4—C3 | 118.5 (2) | C14—C15—H15A | 108.9 |
C9—C4—C3 | 122.7 (2) | C16—C15—H15A | 108.9 |
C4—C5—C6 | 120.6 (3) | C14—C15—H15B | 108.9 |
C4—C5—H5 | 119.7 | C16—C15—H15B | 108.9 |
C6—C5—H5 | 119.7 | H15A—C15—H15B | 107.7 |
C7—C6—C5 | 120.4 (3) | C10—C16—C17 | 113.2 (2) |
C7—C6—H6 | 119.8 | C10—C16—C15 | 107.4 (2) |
C5—C6—H6 | 119.8 | C17—C16—C15 | 114.8 (2) |
C8—C7—C6 | 119.9 (3) | C10—C16—H16 | 107 |
C8—C7—H7 | 120.1 | C17—C16—H16 | 107 |
C6—C7—H7 | 120.1 | C15—C16—H16 | 107 |
C7—C8—C9 | 120.1 (3) | C18—C17—C16 | 113.3 (3) |
C7—C8—H8 | 119.9 | C18—C17—C19 | 111.5 (3) |
C9—C8—H8 | 119.9 | C16—C17—C19 | 111.6 (3) |
C4—C9—C8 | 120.2 (3) | C18—C17—H17 | 106.6 |
C4—C9—H9 | 119.9 | C16—C17—H17 | 106.6 |
C8—C9—H9 | 119.9 | C19—C17—H17 | 106.6 |
O3—C10—C16 | 108.4 (2) | C17—C18—H18A | 109.5 |
O3—C10—C11 | 108.57 (19) | C17—C18—H18B | 109.5 |
C16—C10—C11 | 113.3 (2) | H18A—C18—H18B | 109.5 |
O3—C10—H10 | 108.8 | C17—C18—H18C | 109.5 |
C16—C10—H10 | 108.8 | H18A—C18—H18C | 109.5 |
C11—C10—H10 | 108.8 | H18B—C18—H18C | 109.5 |
C10—C11—C12 | 111.9 (2) | C17—C19—H19A | 109.5 |
C10—C11—H11A | 109.2 | C17—C19—H19B | 109.5 |
C12—C11—H11A | 109.2 | H19A—C19—H19B | 109.5 |
C10—C11—H11B | 109.2 | C17—C19—H19C | 109.5 |
C12—C11—H11B | 109.2 | H19A—C19—H19C | 109.5 |
H11A—C11—H11B | 107.9 | H19B—C19—H19C | 109.5 |
C14—C12—C11 | 109.0 (2) | C2—O1—C3 | 62.09 (15) |
C14—C12—C13 | 111.3 (2) | C1—O3—C10 | 118.04 (17) |
C11—C12—C13 | 112.3 (3) | | |
| | | |
O2—C1—C2—O1 | 11.5 (4) | C10—C11—C12—C14 | 55.4 (3) |
O3—C1—C2—O1 | −167.44 (18) | C10—C11—C12—C13 | 179.2 (3) |
O2—C1—C2—C3 | 79.3 (3) | C11—C12—C14—C15 | −54.6 (4) |
O3—C1—C2—C3 | −99.6 (2) | C13—C12—C14—C15 | −179.0 (3) |
C1—C2—C3—O1 | −104.9 (3) | C12—C14—C15—C16 | 56.2 (4) |
O1—C2—C3—C4 | 105.4 (3) | O3—C10—C16—C17 | −56.6 (3) |
C1—C2—C3—C4 | 0.4 (4) | C11—C10—C16—C17 | −177.1 (2) |
O1—C3—C4—C5 | −179.7 (2) | O3—C10—C16—C15 | 175.7 (2) |
C2—C3—C4—C5 | 111.2 (3) | C11—C10—C16—C15 | 55.1 (3) |
O1—C3—C4—C9 | 1.2 (3) | C14—C15—C16—C10 | −54.1 (3) |
C2—C3—C4—C9 | −67.9 (3) | C14—C15—C16—C17 | 179.0 (3) |
C9—C4—C5—C6 | 1.5 (4) | C10—C16—C17—C18 | −64.0 (4) |
C3—C4—C5—C6 | −177.7 (2) | C15—C16—C17—C18 | 59.8 (4) |
C4—C5—C6—C7 | −0.7 (4) | C10—C16—C17—C19 | 169.1 (3) |
C5—C6—C7—C8 | −0.7 (5) | C15—C16—C17—C19 | −67.0 (4) |
C6—C7—C8—C9 | 1.2 (4) | C1—C2—O1—C3 | 109.6 (2) |
C5—C4—C9—C8 | −0.9 (4) | C4—C3—O1—C2 | −113.3 (2) |
C3—C4—C9—C8 | 178.2 (2) | O2—C1—O3—C10 | −6.8 (3) |
C7—C8—C9—C4 | −0.5 (4) | C2—C1—O3—C10 | 172.24 (19) |
O3—C10—C11—C12 | −178.8 (2) | C16—C10—O3—C1 | 141.5 (2) |
C16—C10—C11—C12 | −58.3 (3) | C11—C10—O3—C1 | −95.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.98 | 2.60 | 3.290 (4) | 127 |
C3—H3···O2i | 0.98 | 2.69 | 3.350 (4) | 125 |
C6—H6···O2ii | 0.93 | 2.70 | 3.486 (4) | 143 |
C7—H7···O1ii | 0.93 | 2.69 | 3.342 (5) | 128 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |