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The relative configuration of the title molecule, C7H10O3, has been determined. The asymmetric C atoms are of opposite chirality (R,S or S,R), as opposed to having the same chirality (R,R or S,S). The molecule adopts an antiperiplanar conformation around the bond connecting the cyclopropyl and carbonyl groups. In the crystal structure, molecules form hydrogen-bonded chains.
Supporting information
CCDC reference: 232141
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.001 Å
- R factor = 0.035
- wR factor = 0.104
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.837 0.988
Tmin' and Tmax expected: 0.937 0.988
RR' = 0.893
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998-2000); cell refinement: SAINT (Bruker, 1998-2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998-2000); software used to prepare material for publication: SHELXTL.
Methyl (
R*,
S*)-2-(2'-methylenecyclopropyl)hydroxyacetate
top
Crystal data top
C7H10O3 | F(000) = 304 |
Mr = 142.15 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Melting point: 41-42 C K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2608 (2) Å | Cell parameters from 4735 reflections |
b = 5.0643 (2) Å | θ = 2.8–30.9° |
c = 19.9397 (6) Å | µ = 0.10 mm−1 |
β = 92.89 (1)° | T = 120 K |
V = 732.27 (4) Å3 | Plate, colourless |
Z = 4 | 0.64 × 0.22 × 0.12 mm |
Data collection top
Bruker SMART CCD 6000 diffractometer | 2017 independent reflections |
Radiation source: fine-focus sealed tube | 1830 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 29.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→9 |
Tmin = 0.837, Tmax = 0.988 | k = −6→7 |
7561 measured reflections | l = −27→27 |
Refinement top
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)] = 0.035 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
2017 reflections | (Δ/σ)max < 0.001 |
131 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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 | Uiso*/Ueq | |
O1 | 0.02777 (9) | 0.66252 (12) | 0.22310 (3) | 0.02635 (16) | |
O2 | 0.32828 (9) | 0.95797 (12) | 0.22305 (3) | 0.02657 (17) | |
O3 | 0.45057 (8) | 0.71013 (13) | 0.14297 (3) | 0.02432 (16) | |
C1 | 0.15259 (13) | 0.32160 (17) | 0.06827 (4) | 0.02605 (19) | |
C2 | 0.08828 (11) | 0.54139 (15) | 0.10876 (4) | 0.02167 (18) | |
C3 | −0.03273 (13) | 0.29705 (18) | 0.09348 (5) | 0.0302 (2) | |
C4 | 0.28885 (16) | 0.2172 (2) | 0.03646 (5) | 0.0356 (2) | |
C5 | 0.16446 (10) | 0.57295 (14) | 0.18049 (4) | 0.01939 (17) | |
C6 | 0.32165 (10) | 0.77176 (15) | 0.18547 (4) | 0.01943 (17) | |
C7 | 0.61188 (12) | 0.8784 (2) | 0.14620 (5) | 0.0290 (2) | |
H1O | −0.023 (2) | 0.529 (3) | 0.2360 (7) | 0.045 (4)* | |
H2 | 0.0465 (16) | 0.707 (3) | 0.0873 (6) | 0.030 (3)* | |
H31 | −0.0516 (17) | 0.181 (3) | 0.1300 (7) | 0.034 (3)* | |
H32 | −0.1359 (19) | 0.315 (3) | 0.0627 (7) | 0.041 (3)* | |
H41 | 0.278 (2) | 0.047 (3) | 0.0157 (7) | 0.047 (4)* | |
H42 | 0.402 (2) | 0.316 (3) | 0.0320 (7) | 0.052 (4)* | |
H5 | 0.2174 (15) | 0.406 (2) | 0.1959 (5) | 0.021 (2)* | |
H71 | 0.582 (2) | 1.061 (3) | 0.1420 (7) | 0.045 (4)* | |
H72 | 0.680 (2) | 0.834 (3) | 0.1071 (7) | 0.043 (4)* | |
H73 | 0.682 (2) | 0.845 (3) | 0.1860 (7) | 0.045 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0288 (3) | 0.0199 (3) | 0.0317 (3) | −0.0034 (2) | 0.0140 (2) | −0.0030 (2) |
O2 | 0.0291 (3) | 0.0213 (3) | 0.0295 (3) | −0.0026 (2) | 0.0036 (2) | −0.0058 (2) |
O3 | 0.0203 (3) | 0.0289 (3) | 0.0241 (3) | −0.0035 (2) | 0.0038 (2) | −0.0040 (2) |
C1 | 0.0350 (4) | 0.0231 (4) | 0.0199 (4) | −0.0031 (3) | −0.0008 (3) | −0.0010 (3) |
C2 | 0.0230 (4) | 0.0187 (4) | 0.0232 (4) | −0.0023 (3) | 0.0001 (3) | 0.0013 (3) |
C3 | 0.0318 (4) | 0.0270 (4) | 0.0315 (4) | −0.0097 (3) | −0.0024 (3) | −0.0013 (3) |
C4 | 0.0497 (6) | 0.0328 (5) | 0.0248 (4) | 0.0034 (4) | 0.0063 (4) | −0.0040 (3) |
C5 | 0.0226 (4) | 0.0159 (3) | 0.0200 (3) | −0.0007 (3) | 0.0043 (3) | −0.0004 (2) |
C6 | 0.0212 (3) | 0.0182 (3) | 0.0190 (3) | 0.0006 (3) | 0.0011 (3) | 0.0020 (2) |
C7 | 0.0205 (4) | 0.0386 (5) | 0.0279 (4) | −0.0072 (3) | 0.0015 (3) | 0.0000 (3) |
Geometric parameters (Å, º) top
O1—C5 | 1.4133 (9) | C2—H2 | 0.982 (13) |
O1—H1O | 0.819 (17) | C3—H31 | 0.950 (13) |
O2—C6 | 1.2039 (10) | C3—H32 | 0.948 (14) |
O3—C6 | 1.3311 (9) | C4—H41 | 0.958 (15) |
O3—C7 | 1.4473 (10) | C4—H42 | 0.967 (16) |
C1—C4 | 1.3130 (14) | C5—C6 | 1.5214 (10) |
C1—C3 | 1.4653 (13) | C5—H5 | 0.973 (11) |
C1—C2 | 1.4651 (12) | C7—H71 | 0.954 (15) |
C2—C5 | 1.5157 (10) | C7—H72 | 0.971 (14) |
C2—C3 | 1.5391 (11) | C7—H73 | 0.936 (15) |
| | | |
C5—O1—H1O | 105.3 (11) | C1—C4—H42 | 120.0 (9) |
C6—O3—C7 | 115.29 (7) | H41—C4—H42 | 118.5 (13) |
C4—C1—C3 | 149.20 (9) | O1—C5—C2 | 111.54 (6) |
C4—C1—C2 | 147.23 (9) | O1—C5—C6 | 107.19 (6) |
C3—C1—C2 | 63.37 (6) | C2—C5—C6 | 111.61 (6) |
C1—C2—C5 | 119.26 (7) | O1—C5—H5 | 111.6 (7) |
C1—C2—C3 | 58.32 (6) | C2—C5—H5 | 109.0 (6) |
C5—C2—C3 | 116.68 (7) | C6—C5—H5 | 105.8 (7) |
C1—C2—H2 | 120.5 (7) | O2—C6—O3 | 124.93 (7) |
C5—C2—H2 | 114.3 (7) | O2—C6—C5 | 124.42 (7) |
C3—C2—H2 | 116.0 (7) | O3—C6—C5 | 110.64 (6) |
C1—C3—C2 | 58.31 (6) | O3—C7—H71 | 112.9 (9) |
C1—C3—H31 | 119.0 (8) | O3—C7—H72 | 105.8 (9) |
C2—C3—H31 | 116.6 (8) | H71—C7—H72 | 106.1 (12) |
C1—C3—H32 | 118.6 (8) | O3—C7—H73 | 109.8 (9) |
C2—C3—H32 | 118.4 (9) | H71—C7—H73 | 111.1 (13) |
H31—C3—H32 | 114.5 (11) | H72—C7—H73 | 111.1 (13) |
C1—C4—H41 | 121.5 (9) | | |
| | | |
C4—C1—C2—C5 | −70.12 (17) | C3—C2—C5—C6 | 163.98 (7) |
C3—C1—C2—C5 | 105.01 (8) | C7—O3—C6—O2 | 2.91 (12) |
C4—C1—C2—C3 | −175.13 (17) | C7—O3—C6—C5 | −176.69 (6) |
C4—C1—C3—C2 | 174.85 (17) | O1—C5—C6—O2 | 4.73 (10) |
C5—C2—C3—C1 | −109.43 (8) | C2—C5—C6—O2 | 127.13 (8) |
C1—C2—C5—O1 | −143.05 (7) | O1—C5—C6—O3 | −175.67 (6) |
C3—C2—C5—O1 | −76.14 (9) | C2—C5—C6—O3 | −53.26 (8) |
C1—C2—C5—C6 | 97.07 (8) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1i | 0.819 (17) | 2.027 (16) | 2.7873 (5) | 154.1 (15) |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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