Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056443/ym2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056443/ym2046Isup2.hkl |
CCDC reference: 636848
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.134
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
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 27.99 From the CIF: _reflns_number_total 1536 Count of symmetry unique reflns 1547 Completeness (_total/calc) 99.29% 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 C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 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 0 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
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C12H20O2 | F(000) = 216 |
Mr = 196.28 | Dx = 1.099 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4218 reflections |
a = 6.9388 (6) Å | θ = 1.6–28.0° |
b = 6.7185 (6) Å | µ = 0.07 mm−1 |
c = 12.9422 (11) Å | T = 295 K |
β = 100.563 (2)° | Block, colourless |
V = 593.12 (9) Å3 | 0.38 × 0.33 × 0.24 mm |
Z = 2 |
Bruker SMART 1K CCD area-detector diffractometer | 1536 independent reflections |
Radiation source: normal-focus sealed tube | 1449 reflections with I > 2/s(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 28.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001a) | h = −8→9 |
Tmin = 0.889, Tmax = 0.992 | k = −8→8 |
4218 measured reflections | l = −17→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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0904P)2 + 0.0286P] where P = (Fo2 + 2Fc2)/3 |
1536 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
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. Friedel pairs were merged before refinement |
x | y | z | Uiso*/Ueq | ||
O1 | 0.3613 (2) | 0.1269 (3) | 0.56458 (11) | 0.0579 (4) | |
H11 | 0.2774 | 0.0877 | 0.5158 | 0.069* | |
O2 | −0.2962 (3) | 0.3104 (4) | 0.55797 (18) | 0.0955 (9) | |
H21 | −0.3938 | 0.2408 | 0.5561 | 0.115* | |
C1 | 0.3009 (3) | 0.0832 (3) | 0.66260 (15) | 0.0465 (4) | |
H1 | 0.1917 | −0.0114 | 0.6490 | 0.056* | |
C2 | 0.2259 (3) | 0.2780 (3) | 0.70185 (14) | 0.0437 (4) | |
H2 | 0.3284 | 0.3780 | 0.7009 | 0.052* | |
C3 | 0.2017 (3) | 0.2541 (3) | 0.81787 (14) | 0.0474 (4) | |
H3 | 0.1178 | 0.1378 | 0.8215 | 0.057* | |
C4 | 0.4030 (3) | 0.2085 (4) | 0.88542 (17) | 0.0619 (6) | |
H41 | 0.4815 | 0.3289 | 0.8934 | 0.074* | |
H42 | 0.3854 | 0.1668 | 0.9548 | 0.074* | |
C5 | 0.5100 (3) | 0.0498 (4) | 0.83840 (19) | 0.0602 (6) | |
H5 | 0.6150 | −0.0112 | 0.8818 | 0.072* | |
C6 | 0.4665 (3) | −0.0112 (3) | 0.73917 (18) | 0.0533 (5) | |
C7 | 0.0420 (3) | 0.3534 (4) | 0.62897 (15) | 0.0517 (5) | |
H71 | 0.0122 | 0.4858 | 0.6514 | 0.062* | |
H72 | 0.0697 | 0.3642 | 0.5584 | 0.062* | |
C8 | −0.1368 (3) | 0.2238 (4) | 0.62551 (18) | 0.0579 (5) | |
H81 | −0.1117 | 0.0920 | 0.6004 | 0.070* | |
H82 | −0.1667 | 0.2109 | 0.6955 | 0.070* | |
C9 | 0.1058 (3) | 0.4295 (4) | 0.86050 (16) | 0.0548 (5) | |
C10 | −0.0519 (4) | 0.4052 (5) | 0.9040 (2) | 0.0764 (8) | |
H101 | −0.1078 | 0.5142 | 0.9316 | 0.092* | |
H102 | −0.1064 | 0.2793 | 0.9068 | 0.092* | |
C11 | 0.1942 (5) | 0.6304 (4) | 0.8556 (2) | 0.0772 (8) | |
H111 | 0.1040 | 0.7298 | 0.8709 | 0.116* | |
H112 | 0.2217 | 0.6525 | 0.7865 | 0.116* | |
H113 | 0.3137 | 0.6385 | 0.9063 | 0.116* | |
C12 | 0.5697 (4) | −0.1812 (4) | 0.6980 (2) | 0.0713 (7) | |
H121 | 0.6739 | −0.2274 | 0.7519 | 0.107* | |
H122 | 0.6231 | −0.1376 | 0.6384 | 0.107* | |
H123 | 0.4785 | −0.2875 | 0.6772 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0555 (8) | 0.0716 (10) | 0.0482 (7) | −0.0111 (8) | 0.0136 (6) | −0.0049 (7) |
O2 | 0.0482 (9) | 0.128 (2) | 0.1017 (14) | −0.0177 (11) | −0.0090 (9) | 0.0650 (15) |
C1 | 0.0427 (9) | 0.0490 (10) | 0.0481 (9) | −0.0106 (8) | 0.0088 (7) | 0.0000 (8) |
C2 | 0.0417 (8) | 0.0462 (9) | 0.0434 (8) | −0.0126 (7) | 0.0081 (7) | 0.0034 (7) |
C3 | 0.0465 (9) | 0.0525 (10) | 0.0429 (8) | −0.0109 (8) | 0.0075 (7) | 0.0033 (8) |
C4 | 0.0552 (12) | 0.0809 (16) | 0.0467 (9) | −0.0080 (12) | 0.0013 (8) | −0.0008 (10) |
C5 | 0.0468 (10) | 0.0669 (14) | 0.0626 (12) | −0.0025 (10) | −0.0012 (8) | 0.0137 (11) |
C6 | 0.0452 (9) | 0.0509 (11) | 0.0644 (11) | −0.0064 (9) | 0.0113 (8) | 0.0072 (10) |
C7 | 0.0499 (10) | 0.0557 (11) | 0.0493 (9) | −0.0060 (10) | 0.0086 (8) | 0.0121 (9) |
C8 | 0.0462 (10) | 0.0668 (13) | 0.0573 (10) | −0.0072 (10) | 0.0002 (8) | 0.0119 (10) |
C9 | 0.0583 (12) | 0.0590 (12) | 0.0482 (9) | −0.0085 (10) | 0.0127 (8) | −0.0008 (8) |
C10 | 0.0760 (17) | 0.0796 (18) | 0.0826 (16) | −0.0053 (14) | 0.0383 (14) | −0.0026 (15) |
C11 | 0.095 (2) | 0.0612 (14) | 0.0811 (16) | −0.0208 (15) | 0.0310 (15) | −0.0142 (13) |
C12 | 0.0675 (14) | 0.0579 (14) | 0.0909 (17) | 0.0042 (12) | 0.0210 (13) | 0.0065 (12) |
O1—C1 | 1.437 (2) | C5—H5 | 0.9300 |
O1—H11 | 0.8200 | C6—C12 | 1.498 (4) |
O2—C8 | 1.404 (3) | C7—C8 | 1.509 (3) |
O2—H21 | 0.8200 | C7—H71 | 0.9700 |
C1—C6 | 1.512 (3) | C7—H72 | 0.9700 |
C1—C2 | 1.529 (3) | C8—H81 | 0.9700 |
C1—H1 | 0.9800 | C8—H82 | 0.9700 |
C2—C7 | 1.527 (3) | C9—C10 | 1.329 (3) |
C2—C3 | 1.550 (2) | C9—C11 | 1.489 (4) |
C2—H2 | 0.9800 | C10—H101 | 0.9300 |
C3—C9 | 1.507 (3) | C10—H102 | 0.9300 |
C3—C4 | 1.537 (3) | C11—H111 | 0.9600 |
C3—H3 | 0.9800 | C11—H112 | 0.9600 |
C4—C5 | 1.491 (4) | C11—H113 | 0.9600 |
C4—H41 | 0.9700 | C12—H121 | 0.9600 |
C4—H42 | 0.9700 | C12—H122 | 0.9600 |
C5—C6 | 1.329 (4) | C12—H123 | 0.9600 |
C1—O1—H11 | 109.5 | C12—C6—C1 | 116.2 (2) |
C8—O2—H21 | 109.5 | C8—C7—C2 | 114.59 (17) |
O1—C1—C6 | 110.77 (16) | C8—C7—H71 | 108.6 |
O1—C1—C2 | 106.87 (15) | C2—C7—H71 | 108.6 |
C6—C1—C2 | 113.90 (16) | C8—C7—H72 | 108.6 |
O1—C1—H1 | 108.4 | C2—C7—H72 | 108.6 |
C6—C1—H1 | 108.4 | H71—C7—H72 | 107.6 |
C2—C1—H1 | 108.4 | O2—C8—C7 | 109.2 (2) |
C7—C2—C1 | 112.04 (16) | O2—C8—H81 | 109.8 |
C7—C2—C3 | 113.95 (16) | C7—C8—H81 | 109.8 |
C1—C2—C3 | 109.70 (15) | O2—C8—H82 | 109.8 |
C7—C2—H2 | 106.9 | C7—C8—H82 | 109.8 |
C1—C2—H2 | 106.9 | H81—C8—H82 | 108.3 |
C3—C2—H2 | 106.9 | C10—C9—C11 | 120.4 (3) |
C9—C3—C4 | 111.33 (18) | C10—C9—C3 | 120.8 (2) |
C9—C3—C2 | 114.04 (17) | C11—C9—C3 | 118.75 (19) |
C4—C3—C2 | 108.84 (17) | C9—C10—H101 | 120.0 |
C9—C3—H3 | 107.4 | C9—C10—H102 | 120.0 |
C4—C3—H3 | 107.4 | H101—C10—H102 | 120.0 |
C2—C3—H3 | 107.4 | C9—C11—H111 | 109.5 |
C5—C4—C3 | 112.25 (18) | C9—C11—H112 | 109.5 |
C5—C4—H41 | 109.2 | H111—C11—H112 | 109.5 |
C3—C4—H41 | 109.2 | C9—C11—H113 | 109.5 |
C5—C4—H42 | 109.2 | H111—C11—H113 | 109.5 |
C3—C4—H42 | 109.2 | H112—C11—H113 | 109.5 |
H41—C4—H42 | 107.9 | C6—C12—H121 | 109.5 |
C6—C5—C4 | 125.0 (2) | C6—C12—H122 | 109.5 |
C6—C5—H5 | 117.5 | H121—C12—H122 | 109.5 |
C4—C5—H5 | 117.5 | C6—C12—H123 | 109.5 |
C5—C6—C12 | 122.7 (2) | H121—C12—H123 | 109.5 |
C5—C6—C1 | 121.0 (2) | H122—C12—H123 | 109.5 |
O1—C1—C2—C7 | 64.91 (18) | C4—C5—C6—C1 | 1.4 (4) |
C6—C1—C2—C7 | −172.42 (16) | O1—C1—C6—C5 | 133.9 (2) |
O1—C1—C2—C3 | −167.48 (14) | C2—C1—C6—C5 | 13.4 (3) |
C6—C1—C2—C3 | −44.8 (2) | O1—C1—C6—C12 | −48.9 (2) |
C7—C2—C3—C9 | −46.6 (2) | C2—C1—C6—C12 | −169.42 (17) |
C1—C2—C3—C9 | −173.13 (16) | C1—C2—C7—C8 | 66.8 (2) |
C7—C2—C3—C4 | −171.56 (19) | C3—C2—C7—C8 | −58.5 (3) |
C1—C2—C3—C4 | 61.9 (2) | C2—C7—C8—O2 | 178.8 (2) |
C9—C3—C4—C5 | −173.83 (18) | C4—C3—C9—C10 | −110.6 (3) |
C2—C3—C4—C5 | −47.3 (3) | C2—C3—C9—C10 | 125.7 (2) |
C3—C4—C5—C6 | 16.6 (3) | C4—C3—C9—C11 | 67.8 (3) |
C4—C5—C6—C12 | −175.5 (2) | C2—C3—C9—C11 | −55.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O2i | 0.82 | 2.11 | 2.641 (3) | 123 |
O2—H21···O1ii | 0.82 | 1.89 | 2.693 (2) | 168 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x−1, y, z. |
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