Buy article online - an online subscription or single-article purchase is required to access this article.
organic compounds
The title compound, C18H18O3, was synthesized with pure optically active reagents. The molecules possess two chiral atoms and are linked through O—HO hydrogen bonds in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019174/bx2072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019174/bx2072Isup2.hkl |
CCDC reference: 648059
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.046
- wR factor = 0.140
- Data-to-parameter ratio = 7.9
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.115 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.87 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT362_ALERT_2_C Short C(sp3)-C(sp2) Bond C16 - C17 ... 1.40 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 25.10 From the CIF: _reflns_number_total 1511 Count of symmetry unique reflns 1517 Completeness (_total/calc) 99.60% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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
Computing details top
Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1997); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL-Plus.
(R,R)-(+)-2-(2-Methacryloyloxy)-1,2-diphenylethanol top
Crystal data top
C18H18O3 | F(000) = 300 |
Mr = 282.32 | Dx = 1.222 Mg m−3 |
Monoclinic, P21 | Melting point = 360–362 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 12.094 (5) Å | Cell parameters from 40 reflections |
b = 5.756 (3) Å | θ = 3.8–10.0° |
c = 12.503 (6) Å | µ = 0.08 mm−1 |
β = 118.18 (2)° | T = 298 K |
V = 767.1 (6) Å3 | Needle, colourless |
Z = 2 | 0.60 × 0.12 × 0.05 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.115 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.9° |
Graphite monochromator | h = −14→14 |
θ/2θ scans | k = −6→6 |
6004 measured reflections | l = −14→14 |
1511 independent reflections | 3 standard reflections every 97 reflections |
907 reflections with I > 2σ(I) | intensity decay: 3.8% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.140 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.16 e Å−3 |
1511 reflections | Δρmin = −0.13 e Å−3 |
192 parameters | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.034 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack, 1983 (1214 Friedel pairs) |
Secondary atom site location: difference Fourier map |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.5302 (2) | 0.3349 (9) | 0.4764 (3) | 0.0903 (12) | |
H1A | 0.5542 | 0.2365 | 0.5361 | 0.135* | |
O2 | 0.4227 (2) | 0.3360 (6) | 0.2331 (3) | 0.0715 (9) | |
O3 | 0.3725 (3) | 0.6872 (8) | 0.2676 (3) | 0.0941 (12) | |
C1 | 0.7034 (4) | 0.4486 (10) | 0.2203 (3) | 0.0730 (14) | |
H1B | 0.7269 | 0.5869 | 0.2640 | 0.088* | |
C2 | 0.7592 (5) | 0.3872 (15) | 0.1499 (5) | 0.098 (2) | |
H2A | 0.8200 | 0.4826 | 0.1473 | 0.117* | |
C3 | 0.7254 (6) | 0.1899 (15) | 0.0855 (5) | 0.102 (2) | |
H3A | 0.7624 | 0.1485 | 0.0378 | 0.122* | |
C4 | 0.6368 (5) | 0.0495 (13) | 0.0899 (4) | 0.0946 (18) | |
H4A | 0.6127 | −0.0865 | 0.0444 | 0.113* | |
C5 | 0.5825 (4) | 0.1092 (10) | 0.1618 (4) | 0.0769 (14) | |
H5A | 0.5235 | 0.0109 | 0.1658 | 0.092* | |
C6 | 0.6150 (3) | 0.3125 (9) | 0.2275 (3) | 0.0590 (11) | |
C7 | 0.5559 (3) | 0.3818 (9) | 0.3037 (3) | 0.0580 (11) | |
H7A | 0.5685 | 0.5489 | 0.3201 | 0.070* | |
C8 | 0.6032 (3) | 0.2534 (9) | 0.4229 (4) | 0.0662 (13) | |
H8A | 0.5884 | 0.0866 | 0.4067 | 0.079* | |
C9 | 0.7409 (4) | 0.2944 (9) | 0.5021 (3) | 0.0597 (12) | |
C10 | 0.7830 (4) | 0.4953 (10) | 0.5684 (4) | 0.0736 (14) | |
H10A | 0.7255 | 0.6056 | 0.5657 | 0.088* | |
C11 | 0.9096 (5) | 0.5351 (12) | 0.6390 (4) | 0.0818 (15) | |
H11A | 0.9366 | 0.6729 | 0.6826 | 0.098* | |
C12 | 0.9965 (4) | 0.3738 (12) | 0.6458 (4) | 0.0782 (15) | |
H12A | 1.0818 | 0.4002 | 0.6947 | 0.094* | |
C13 | 0.9563 (4) | 0.1782 (11) | 0.5807 (4) | 0.0756 (15) | |
H13A | 1.0144 | 0.0696 | 0.5831 | 0.091* | |
C14 | 0.8290 (4) | 0.1354 (9) | 0.5098 (3) | 0.0664 (13) | |
H14A | 0.8030 | −0.0033 | 0.4668 | 0.080* | |
C15 | 0.3419 (4) | 0.4934 (12) | 0.2268 (4) | 0.0665 (14) | |
C16 | 0.2117 (4) | 0.4072 (11) | 0.1686 (4) | 0.0726 (15) | |
C17 | 0.1869 (5) | 0.1821 (13) | 0.1195 (6) | 0.112 (2) | |
H17A | 0.2073 | 0.1733 | 0.0541 | 0.168* | |
H17B | 0.0997 | 0.1471 | 0.0895 | 0.168* | |
H17C | 0.2369 | 0.0722 | 0.1812 | 0.168* | |
C18 | 0.1213 (5) | 0.5536 (15) | 0.1676 (5) | 0.1026 (19) | |
H18A | 0.0381 | 0.5050 | 0.1330 | 0.123* | |
H18B | 0.1432 | 0.7011 | 0.2015 | 0.123* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0764 (19) | 0.117 (3) | 0.093 (2) | 0.026 (2) | 0.0524 (16) | 0.030 (2) |
O2 | 0.0547 (15) | 0.066 (2) | 0.0864 (19) | 0.0035 (19) | 0.0269 (14) | −0.0042 (18) |
O3 | 0.074 (2) | 0.081 (3) | 0.114 (3) | 0.017 (2) | 0.0335 (19) | −0.005 (3) |
C1 | 0.079 (3) | 0.074 (4) | 0.068 (2) | −0.008 (3) | 0.037 (2) | −0.001 (3) |
C2 | 0.091 (3) | 0.131 (7) | 0.085 (3) | −0.011 (4) | 0.054 (3) | 0.000 (4) |
C3 | 0.107 (4) | 0.128 (7) | 0.069 (3) | 0.018 (5) | 0.041 (3) | −0.004 (4) |
C4 | 0.098 (4) | 0.094 (5) | 0.074 (3) | 0.019 (4) | 0.026 (3) | −0.017 (3) |
C5 | 0.076 (3) | 0.065 (4) | 0.084 (3) | −0.001 (3) | 0.033 (2) | −0.006 (3) |
C6 | 0.057 (2) | 0.057 (3) | 0.056 (2) | 0.002 (3) | 0.0201 (18) | 0.004 (2) |
C7 | 0.050 (2) | 0.052 (3) | 0.064 (2) | −0.002 (2) | 0.0207 (17) | −0.002 (2) |
C8 | 0.065 (2) | 0.062 (4) | 0.082 (3) | 0.006 (2) | 0.043 (2) | 0.007 (3) |
C9 | 0.065 (2) | 0.064 (3) | 0.054 (2) | 0.009 (3) | 0.0311 (19) | 0.003 (2) |
C10 | 0.082 (3) | 0.069 (4) | 0.068 (3) | 0.016 (3) | 0.035 (2) | 0.003 (3) |
C11 | 0.099 (4) | 0.072 (4) | 0.073 (3) | −0.009 (4) | 0.039 (3) | −0.009 (3) |
C12 | 0.069 (3) | 0.095 (5) | 0.065 (3) | −0.004 (3) | 0.027 (2) | −0.002 (3) |
C13 | 0.061 (3) | 0.095 (5) | 0.067 (3) | 0.013 (3) | 0.027 (2) | −0.003 (3) |
C14 | 0.072 (3) | 0.062 (4) | 0.061 (2) | 0.007 (3) | 0.027 (2) | −0.001 (2) |
C15 | 0.055 (3) | 0.080 (4) | 0.058 (2) | 0.006 (3) | 0.022 (2) | −0.002 (3) |
C16 | 0.056 (2) | 0.101 (5) | 0.056 (2) | 0.001 (3) | 0.0225 (19) | 0.012 (3) |
C17 | 0.075 (3) | 0.123 (7) | 0.119 (4) | −0.016 (4) | 0.030 (3) | −0.033 (5) |
C18 | 0.073 (3) | 0.112 (5) | 0.127 (4) | 0.007 (4) | 0.051 (3) | 0.003 (5) |
Geometric parameters (Å, º) top
O1—C8 | 1.415 (5) | C8—H8A | 0.9800 |
O1—H1A | 0.8703 | C9—C14 | 1.373 (6) |
O2—C15 | 1.308 (6) | C9—C10 | 1.373 (7) |
O2—C7 | 1.450 (4) | C10—C11 | 1.378 (6) |
O3—C15 | 1.209 (7) | C10—H10A | 0.9300 |
C1—C6 | 1.362 (6) | C11—C12 | 1.375 (7) |
C1—C2 | 1.385 (6) | C11—H11A | 0.9300 |
C1—H1B | 0.9300 | C12—C13 | 1.339 (8) |
C2—C3 | 1.339 (9) | C12—H12A | 0.9300 |
C2—H2A | 0.9300 | C13—C14 | 1.389 (6) |
C3—C4 | 1.363 (8) | C13—H13A | 0.9300 |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—C5 | 1.385 (7) | C15—C16 | 1.473 (7) |
C4—H4A | 0.9300 | C16—C18 | 1.377 (8) |
C5—C6 | 1.375 (7) | C16—C17 | 1.404 (8) |
C5—H5A | 0.9300 | C17—H17A | 0.9600 |
C6—C7 | 1.489 (5) | C17—H17B | 0.9600 |
C7—C8 | 1.514 (5) | C17—H17C | 0.9600 |
C7—H7A | 0.9800 | C18—H18A | 0.9300 |
C8—C9 | 1.500 (5) | C18—H18B | 0.9300 |
C8—O1—H1A | 99.2 | C14—C9—C8 | 121.6 (4) |
C15—O2—C7 | 119.7 (4) | C10—C9—C8 | 120.7 (4) |
C6—C1—C2 | 121.9 (5) | C9—C10—C11 | 120.6 (5) |
C6—C1—H1B | 119.1 | C9—C10—H10A | 119.7 |
C2—C1—H1B | 119.1 | C11—C10—H10A | 119.7 |
C3—C2—C1 | 119.8 (6) | C12—C11—C10 | 120.9 (5) |
C3—C2—H2A | 120.1 | C12—C11—H11A | 119.6 |
C1—C2—H2A | 120.1 | C10—C11—H11A | 119.6 |
C2—C3—C4 | 120.1 (6) | C13—C12—C11 | 118.9 (4) |
C2—C3—H3A | 120.0 | C13—C12—H12A | 120.6 |
C4—C3—H3A | 120.0 | C11—C12—H12A | 120.6 |
C3—C4—C5 | 120.1 (6) | C12—C13—C14 | 120.8 (5) |
C3—C4—H4A | 119.9 | C12—C13—H13A | 119.6 |
C5—C4—H4A | 119.9 | C14—C13—H13A | 119.6 |
C6—C5—C4 | 120.6 (5) | C9—C14—C13 | 121.1 (5) |
C6—C5—H5A | 119.7 | C9—C14—H14A | 119.5 |
C4—C5—H5A | 119.7 | C13—C14—H14A | 119.5 |
C1—C6—C5 | 117.5 (4) | O3—C15—O2 | 122.8 (5) |
C1—C6—C7 | 121.1 (4) | O3—C15—C16 | 124.2 (5) |
C5—C6—C7 | 121.4 (4) | O2—C15—C16 | 112.9 (6) |
O2—C7—C6 | 107.0 (3) | C18—C16—C17 | 123.8 (5) |
O2—C7—C8 | 107.7 (3) | C18—C16—C15 | 117.2 (6) |
C6—C7—C8 | 115.3 (3) | C17—C16—C15 | 119.0 (5) |
O2—C7—H7A | 108.9 | C16—C17—H17A | 109.5 |
C6—C7—H7A | 108.9 | C16—C17—H17B | 109.5 |
C8—C7—H7A | 108.9 | H17A—C17—H17B | 109.5 |
O1—C8—C9 | 112.4 (4) | C16—C17—H17C | 109.5 |
O1—C8—C7 | 105.9 (3) | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 111.0 (3) | H17B—C17—H17C | 109.5 |
O1—C8—H8A | 109.1 | C16—C18—H18A | 120.0 |
C9—C8—H8A | 109.1 | C16—C18—H18B | 120.0 |
C7—C8—H8A | 109.1 | H18A—C18—H18B | 120.0 |
C14—C9—C10 | 117.7 (4) | ||
C6—C1—C2—C3 | 0.7 (8) | O1—C8—C9—C14 | 142.5 (4) |
C1—C2—C3—C4 | −0.3 (9) | C7—C8—C9—C14 | −99.1 (5) |
C2—C3—C4—C5 | −0.7 (9) | O1—C8—C9—C10 | −38.4 (6) |
C3—C4—C5—C6 | 1.5 (8) | C7—C8—C9—C10 | 80.0 (5) |
C2—C1—C6—C5 | 0.0 (7) | C14—C9—C10—C11 | 0.6 (6) |
C2—C1—C6—C7 | −179.9 (4) | C8—C9—C10—C11 | −178.5 (4) |
C4—C5—C6—C1 | −1.1 (6) | C9—C10—C11—C12 | −0.8 (7) |
C4—C5—C6—C7 | 178.9 (4) | C10—C11—C12—C13 | 1.2 (7) |
C15—O2—C7—C6 | −133.5 (4) | C11—C12—C13—C14 | −1.6 (7) |
C15—O2—C7—C8 | 101.9 (4) | C10—C9—C14—C13 | −1.0 (6) |
C1—C6—C7—O2 | 136.6 (4) | C8—C9—C14—C13 | 178.1 (4) |
C5—C6—C7—O2 | −43.4 (5) | C12—C13—C14—C9 | 1.5 (7) |
C1—C6—C7—C8 | −103.6 (5) | C7—O2—C15—O3 | 7.4 (6) |
C5—C6—C7—C8 | 76.4 (5) | C7—O2—C15—C16 | −170.9 (3) |
O2—C7—C8—O1 | −57.1 (4) | O3—C15—C16—C18 | −4.0 (7) |
C6—C7—C8—O1 | −176.5 (4) | O2—C15—C16—C18 | 174.2 (4) |
O2—C7—C8—C9 | −179.4 (4) | O3—C15—C16—C17 | 177.0 (5) |
C6—C7—C8—C9 | 61.2 (5) | O2—C15—C16—C17 | −4.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O3i | 0.87 | 2.20 | 2.965 (5) | 147 |
O1—H1A···O1i | 0.87 | 2.50 | 3.094 (7) | 126 |
Symmetry code: (i) −x+1, y−1/2, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register