Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045746/ng2328sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045746/ng2328Isup2.hkl |
CCDC reference: 663816
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.113
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
Author Response: checked, values are correct. |
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 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
For the synthesis of the title compound, see: Becker et al. (2001). [Should some background references be included to back up the comparison statements in the Abstract?]
The title compound was prepared by standard procedures upon acidic aqueous dihydroxylation of cycloheptene with hydrogen peroxide and formic acid (Becker et al., 2001).
All H atoms were located in difference maps and refined with individual isotropic temperature parameters. The C-bonded H atoms were refined as riding on their parent atoms. The O-bonded H atoms were refined with free positional parameters.
The vicinal diol derived from cycloheptane was prepared as a chelating molecule bearing a conformationally flexible seven-membered hydrocarbon ring. The cycloheptane ring adopts a chair-like conformation. Accordingly, the molecular symmetry is close to C2 symmetry (Fig. 1).
In the crystal structure, hydrophobic contacts close to planes with z = 1/4 and 3/4 divide the structure in sheets (Fig. 2). Fig. 3 shows an individual sheet (the one with 1/4 < z < 3/4) in a projection along [001]. The characteristic hydrogen bonds are highlighted. In the hydrogen-bond scheme, each hydroxy function acts both as a single hydrogen-bond donor and acceptor. The individual hydrogen bonds are embedded in cooperative chains of alternating polarity along [010] (green and yellow bonds in Fig. 3).
For the synthesis of the title compound, see: Becker et al. (2001). [Should some background references be included to back up the comparison statements in the Abstract?]
Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997) and DENZO (Otwinowski & Minor, 1997); 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).
C7H14O2 | F(000) = 576 |
Mr = 130.18 | Dx = 1.176 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1964 reflections |
a = 10.1290 (3) Å | θ = 3.1–27.5° |
b = 7.2290 (2) Å | µ = 0.08 mm−1 |
c = 20.0750 (7) Å | T = 200 K |
V = 1469.94 (8) Å3 | Block, colourless |
Z = 8 | 0.24 × 0.15 × 0.06 mm |
Nonius KappaCCD area-detector diffractometer | 1118 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.028 |
MONTEL, graded multilayered X-ray optics monochromator | θmax = 27.5°, θmin = 3.6° |
φ and ω scans | h = −13→13 |
3095 measured reflections | k = −9→9 |
1682 independent reflections | l = −26→25 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.1228P] where P = (Fo2 + 2Fc2)/3 |
1685 reflections | (Δ/σ)max < 0.001 |
102 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C7H14O2 | V = 1469.94 (8) Å3 |
Mr = 130.18 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.1290 (3) Å | µ = 0.08 mm−1 |
b = 7.2290 (2) Å | T = 200 K |
c = 20.0750 (7) Å | 0.24 × 0.15 × 0.06 mm |
Nonius KappaCCD area-detector diffractometer | 1118 reflections with I > 2σ(I) |
3095 measured reflections | Rint = 0.028 |
1682 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.13 e Å−3 |
1685 reflections | Δρmin = −0.18 e Å−3 |
102 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. The refU data value refers to the C-bonded H atoms. The value All H-atom parameters refined applies to the two O-bonded H atoms. Five reflections were regarded as damaged and were excluded from the refinement. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.13320 (10) | 0.85835 (13) | 0.03853 (5) | 0.0407 (3) | |
H81 | −0.2133 (17) | 0.819 (2) | 0.0249 (8) | 0.063 (5)* | |
O2 | 0.12953 (8) | 0.78401 (14) | 0.00365 (5) | 0.0396 (3) | |
H82 | 0.1148 (16) | 0.898 (3) | −0.0124 (10) | 0.070 (6)* | |
C1 | −0.06343 (12) | 0.70624 (17) | 0.06767 (6) | 0.0296 (3) | |
H1 | −0.0705 | 0.5979 | 0.0369 | 0.032 (3)* | |
C2 | 0.08021 (12) | 0.76549 (18) | 0.07061 (6) | 0.0306 (3) | |
H2 | 0.0849 | 0.8892 | 0.0928 | 0.026 (3)* | |
C3 | 0.17267 (13) | 0.63419 (18) | 0.10705 (7) | 0.0369 (4) | |
H31 | 0.2649 | 0.6714 | 0.0978 | 0.040 (4)* | |
H32 | 0.1601 | 0.5078 | 0.0891 | 0.040 (4)* | |
C4 | 0.15183 (14) | 0.6295 (2) | 0.18236 (8) | 0.0431 (4) | |
H41 | 0.2372 | 0.5996 | 0.2038 | 0.051 (4)* | |
H42 | 0.1261 | 0.7549 | 0.1972 | 0.055 (5)* | |
C5 | 0.04863 (14) | 0.4926 (2) | 0.20740 (7) | 0.0450 (4) | |
H51 | 0.0199 | 0.5317 | 0.2524 | 0.060 (5)* | |
H52 | 0.0907 | 0.3696 | 0.2118 | 0.053 (4)* | |
C6 | −0.07353 (14) | 0.4732 (2) | 0.16324 (7) | 0.0420 (4) | |
H61 | −0.1446 | 0.4148 | 0.1898 | 0.057 (5)* | |
H62 | −0.0521 | 0.3883 | 0.1261 | 0.049 (4)* | |
C7 | −0.12639 (12) | 0.65375 (19) | 0.13391 (7) | 0.0354 (3) | |
H71 | −0.2229 | 0.6420 | 0.1276 | 0.048 (4)* | |
H72 | −0.1110 | 0.7549 | 0.1662 | 0.044 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0333 (5) | 0.0345 (6) | 0.0544 (7) | −0.0006 (4) | −0.0094 (5) | 0.0118 (4) |
O2 | 0.0396 (6) | 0.0378 (6) | 0.0414 (6) | 0.0049 (4) | 0.0113 (4) | 0.0086 (5) |
C1 | 0.0299 (7) | 0.0270 (7) | 0.0320 (7) | 0.0012 (5) | −0.0037 (5) | 0.0006 (5) |
C2 | 0.0301 (7) | 0.0287 (7) | 0.0331 (7) | 0.0001 (5) | 0.0031 (5) | −0.0001 (5) |
C3 | 0.0290 (7) | 0.0381 (8) | 0.0436 (9) | 0.0024 (6) | 0.0005 (6) | 0.0029 (6) |
C4 | 0.0393 (8) | 0.0484 (9) | 0.0416 (9) | 0.0003 (6) | −0.0098 (6) | 0.0034 (7) |
C5 | 0.0476 (8) | 0.0488 (9) | 0.0387 (9) | 0.0023 (7) | −0.0023 (7) | 0.0090 (7) |
C6 | 0.0445 (8) | 0.0429 (8) | 0.0385 (8) | −0.0073 (6) | 0.0001 (6) | 0.0094 (6) |
C7 | 0.0278 (7) | 0.0429 (8) | 0.0356 (8) | −0.0016 (6) | 0.0008 (6) | −0.0004 (6) |
O1—C1 | 1.4320 (15) | C4—C5 | 1.524 (2) |
O1—H81 | 0.903 (18) | C4—H41 | 0.9900 |
O2—C2 | 1.4403 (15) | C4—H42 | 0.9900 |
O2—H82 | 0.90 (2) | C5—C6 | 1.529 (2) |
C1—C2 | 1.5179 (18) | C5—H51 | 0.9900 |
C1—C7 | 1.5228 (18) | C5—H52 | 0.9900 |
C1—H1 | 1.0000 | C6—C7 | 1.5288 (19) |
C2—C3 | 1.5209 (18) | C6—H61 | 0.9900 |
C2—H2 | 1.0000 | C6—H62 | 0.9900 |
C3—C4 | 1.527 (2) | C7—H71 | 0.9900 |
C3—H31 | 0.9900 | C7—H72 | 0.9900 |
C3—H32 | 0.9900 | ||
C1—O1—H81 | 108.9 (10) | C3—C4—H41 | 108.3 |
C2—O2—H82 | 111.2 (12) | C5—C4—H42 | 108.3 |
O1—C1—C2 | 105.79 (10) | C3—C4—H42 | 108.3 |
O1—C1—C7 | 109.96 (10) | H41—C4—H42 | 107.4 |
C2—C1—C7 | 115.96 (11) | C4—C5—C6 | 115.05 (12) |
O1—C1—H1 | 108.3 | C4—C5—H51 | 108.5 |
C2—C1—H1 | 108.3 | C6—C5—H51 | 108.5 |
C7—C1—H1 | 108.3 | C4—C5—H52 | 108.5 |
O2—C2—C1 | 108.81 (10) | C6—C5—H52 | 108.5 |
O2—C2—C3 | 107.05 (10) | H51—C5—H52 | 107.5 |
C1—C2—C3 | 115.65 (11) | C5—C6—C7 | 115.36 (12) |
O2—C2—H2 | 108.4 | C5—C6—H61 | 108.4 |
C1—C2—H2 | 108.4 | C7—C6—H61 | 108.4 |
C3—C2—H2 | 108.4 | C5—C6—H62 | 108.4 |
C2—C3—C4 | 113.89 (11) | C7—C6—H62 | 108.4 |
C2—C3—H31 | 108.8 | H61—C6—H62 | 107.5 |
C4—C3—H31 | 108.8 | C1—C7—C6 | 113.73 (11) |
C2—C3—H32 | 108.8 | C1—C7—H71 | 108.8 |
C4—C3—H32 | 108.8 | C6—C7—H71 | 108.8 |
H31—C3—H32 | 107.7 | C1—C7—H72 | 108.8 |
C5—C4—C3 | 115.84 (12) | C6—C7—H72 | 108.8 |
C5—C4—H41 | 108.3 | H71—C7—H72 | 107.7 |
O1—C1—C2—O2 | −66.09 (12) | C2—C3—C4—C5 | 87.55 (15) |
C7—C1—C2—O2 | 171.75 (10) | C3—C4—C5—C6 | −37.73 (18) |
O1—C1—C2—C3 | 173.44 (10) | C4—C5—C6—C7 | −40.52 (19) |
C7—C1—C2—C3 | 51.27 (16) | O1—C1—C7—C6 | 170.39 (11) |
O2—C2—C3—C4 | 168.11 (10) | C2—C1—C7—C6 | −69.68 (15) |
C1—C2—C3—C4 | −70.47 (15) | C5—C6—C7—C1 | 88.08 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H81···O2i | 0.90 (2) | 1.85 (2) | 2.7481 (13) | 174.7 (15) |
O2—H82···O1ii | 0.90 (2) | 1.84 (2) | 2.7208 (14) | 164.0 (15) |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C7H14O2 |
Mr | 130.18 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 200 |
a, b, c (Å) | 10.1290 (3), 7.2290 (2), 20.0750 (7) |
V (Å3) | 1469.94 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.24 × 0.15 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3095, 1682, 1118 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.113, 1.05 |
No. of reflections | 1685 |
No. of parameters | 102 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.13, −0.18 |
Computer programs: COLLECT (Nonius, 2004), SCALEPACK (Otwinowski & Minor, 1997) and DENZO (Otwinowski & Minor, 1997), 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—H81···O2i | 0.90 (2) | 1.85 (2) | 2.7481 (13) | 174.7 (15) |
O2—H82···O1ii | 0.90 (2) | 1.84 (2) | 2.7208 (14) | 164.0 (15) |
Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x, −y+2, −z. |
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The vicinal diol derived from cycloheptane was prepared as a chelating molecule bearing a conformationally flexible seven-membered hydrocarbon ring. The cycloheptane ring adopts a chair-like conformation. Accordingly, the molecular symmetry is close to C2 symmetry (Fig. 1).
In the crystal structure, hydrophobic contacts close to planes with z = 1/4 and 3/4 divide the structure in sheets (Fig. 2). Fig. 3 shows an individual sheet (the one with 1/4 < z < 3/4) in a projection along [001]. The characteristic hydrogen bonds are highlighted. In the hydrogen-bond scheme, each hydroxy function acts both as a single hydrogen-bond donor and acceptor. The individual hydrogen bonds are embedded in cooperative chains of alternating polarity along [010] (green and yellow bonds in Fig. 3).