Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034915/bt2444sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034915/bt2444Isup2.hkl |
CCDC reference: 659096
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.098
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
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 27.56 From the CIF: _reflns_number_total 1442 Count of symmetry unique reflns 1452 Completeness (_total/calc) 99.31% 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 0 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 0 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
For related literature, see: Bromley et al. (1998); Flack (1983); Mues & Buysch (1990); Narasimhamurthy et al. (1990).
The title compound was prepared according to a literature procedure (Mues & Buysch, 1990) by the reaction of dichlorodiphenoxymethane, (PhO)2CCl2, with 1,1-bis(hydroxymethyl)cyclopropane. The crude product was recrystallized from boiling ethyl acetate.
Spectroscopic data: 1H NMR (400 MHz, CDCl3, 22 °C) δ/p.p.m.: 3.79 (s, 8 H, OCH2), 0.55 (s, 8 H, CH2). 13C{1H} NMR (101 MHz, CDCl3, 24 °C) δ/p.p.m.: 114.8 (CO4), 69.1 (OCH2), 16.2 (Cq), 8.9 (CH2). HRMS m/z calculated for C11H16O4 (M+): 212.1043; found: 212.1043.
All H atoms were located in a difference map and refined as riding on their parent atoms. One common isotropic displacement parameter for all H atoms was refined to Uiso(H) = 0.0420 (17).
Due to the absence of significant anomalous scattering the absolute structure parameter (Flack, 1983), which is -3.1 with an estimated standard deviation of 1.2 for the unmerged data set, is meaningless. Thus, Friedel opposites (995 pairs) have been merged and the absolute configuration has been arbitrarily chosen.
The title compound, C11H16O4, a diol ester of the nonexistent orthocarbonic acid C(OH)4, was prepared for the purpose of collecting NMR data on orthocarbonates and for comparison with similar silicon compounds. It was obtained as the product of the reaction between dichlorodiphenoxymethane and 1,1-bis(hydroxymethyl)cyclopropane.
The molecular structure (Fig. 1) shows C2 symmetry. The 1,3-dioxane rings adopt chair conformations. The central carbon atom is in a distorted tetrahedral environment of four oxygen atoms. O11 and O21 are equatorial substituents, O13 and O23 are axial substituents, of their opposing six-membered rings. Due to the anomeric effect, the axial C10–O bonds are slightly, but significantly, longer than the corresponding equatorial bonds. The endocyclic O–C–O angles are significantly larger than the exocyclic ones.
The molecular packing is shown in Fig. 2.
For related literature, see: Bromley et al. (1998); Flack (1983); Mues & Buysch (1990); Narasimhamurthy et al. (1990).
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; 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.
C11H16O4 | F(000) = 456 |
Mr = 212.24 | Dx = 1.331 (1) Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | θ = 4.4–27.5° |
a = 6.2980 (8) Å | µ = 0.10 mm−1 |
b = 7.1520 (8) Å | T = 200 K |
c = 23.508 (3) Å | Block, colourless |
V = 1058.9 (2) Å3 | 0.26 × 0.19 × 0.10 mm |
Z = 4 |
Oxford XCalibur3 diffractometer | 1237 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 27.6°, θmin = 4.4° |
ω scans | h = −8→5 |
6256 measured reflections | k = −8→9 |
1442 independent reflections | l = −28→30 |
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.098 | Only H-atom displacement parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3 |
1442 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C11H16O4 | V = 1058.9 (2) Å3 |
Mr = 212.24 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.2980 (8) Å | µ = 0.10 mm−1 |
b = 7.1520 (8) Å | T = 200 K |
c = 23.508 (3) Å | 0.26 × 0.19 × 0.10 mm |
Oxford XCalibur3 diffractometer | 1237 reflections with I > 2σ(I) |
6256 measured reflections | Rint = 0.044 |
1442 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.098 | Only H-atom displacement parameters refined |
S = 1.08 | Δρmax = 0.16 e Å−3 |
1442 reflections | Δρmin = −0.17 e Å−3 |
137 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. 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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.6614 (3) | 0.7090 (2) | 0.06259 (6) | 0.0344 (4) | |
O13 | 0.6407 (3) | 0.8773 (2) | 0.14710 (6) | 0.0336 (4) | |
O21 | 0.6058 (3) | 0.5650 (2) | 0.14343 (6) | 0.0352 (4) | |
O23 | 0.3442 (2) | 0.7528 (2) | 0.10339 (6) | 0.0318 (4) | |
C10 | 0.5614 (4) | 0.7292 (3) | 0.11423 (9) | 0.0296 (5) | |
C11 | 0.6546 (4) | 0.8783 (3) | 0.02814 (9) | 0.0348 (5) | |
H111 | 0.5061 | 0.9062 | 0.0172 | 0.0420 (17)* | |
H112 | 0.7385 | 0.8602 | −0.0070 | 0.0420 (17)* | |
C12 | 0.7440 (4) | 1.0372 (3) | 0.06173 (10) | 0.0317 (5) | |
C13 | 0.6326 (4) | 1.0554 (3) | 0.11755 (9) | 0.0345 (5) | |
H131 | 0.7021 | 1.1532 | 0.1408 | 0.0420 (17)* | |
H132 | 0.4830 | 1.0925 | 0.1113 | 0.0420 (17)* | |
C14 | 0.8256 (4) | 1.2072 (3) | 0.03185 (11) | 0.0405 (6) | |
H141 | 0.8046 | 1.3298 | 0.0505 | 0.0420 (17)* | |
H142 | 0.8179 | 1.2095 | −0.0102 | 0.0420 (17)* | |
C15 | 0.9787 (4) | 1.0718 (3) | 0.05907 (11) | 0.0388 (6) | |
H151 | 1.0645 | 0.9912 | 0.0337 | 0.0420 (17)* | |
H152 | 1.0512 | 1.1116 | 0.0944 | 0.0420 (17)* | |
C21 | 0.4940 (4) | 0.5515 (4) | 0.19660 (10) | 0.0364 (5) | |
H211 | 0.5467 | 0.6485 | 0.2231 | 0.0420 (17)* | |
H212 | 0.5206 | 0.4276 | 0.2140 | 0.0420 (17)* | |
C22 | 0.2604 (4) | 0.5770 (3) | 0.18734 (10) | 0.0321 (5) | |
C23 | 0.2164 (4) | 0.7525 (3) | 0.15418 (9) | 0.0347 (5) | |
H231 | 0.0641 | 0.7583 | 0.1439 | 0.0420 (17)* | |
H232 | 0.2507 | 0.8634 | 0.1777 | 0.0420 (17)* | |
C24 | 0.1061 (4) | 0.5146 (4) | 0.23182 (9) | 0.0421 (6) | |
H241 | −0.0228 | 0.5914 | 0.2378 | 0.0420 (17)* | |
H242 | 0.1639 | 0.4555 | 0.2666 | 0.0420 (17)* | |
C25 | 0.1253 (4) | 0.4088 (3) | 0.17680 (10) | 0.0412 (6) | |
H251 | 0.1948 | 0.2847 | 0.1778 | 0.0420 (17)* | |
H252 | 0.0081 | 0.4205 | 0.1490 | 0.0420 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0381 (9) | 0.0323 (8) | 0.0328 (8) | 0.0006 (7) | 0.0067 (8) | −0.0034 (6) |
O13 | 0.0376 (9) | 0.0336 (8) | 0.0296 (7) | −0.0023 (7) | −0.0019 (8) | −0.0025 (6) |
O21 | 0.0300 (8) | 0.0349 (8) | 0.0408 (8) | 0.0072 (7) | 0.0012 (8) | 0.0047 (7) |
O23 | 0.0246 (7) | 0.0404 (8) | 0.0303 (7) | 0.0003 (7) | −0.0017 (7) | 0.0030 (7) |
C10 | 0.0285 (11) | 0.0304 (11) | 0.0299 (10) | 0.0008 (9) | 0.0012 (9) | 0.0001 (9) |
C11 | 0.0364 (13) | 0.0385 (12) | 0.0294 (11) | −0.0017 (11) | 0.0032 (11) | 0.0028 (9) |
C12 | 0.0291 (11) | 0.0323 (11) | 0.0336 (11) | 0.0020 (10) | 0.0000 (10) | 0.0035 (9) |
C13 | 0.0379 (13) | 0.0283 (11) | 0.0374 (11) | −0.0007 (11) | 0.0011 (11) | −0.0040 (9) |
C14 | 0.0390 (13) | 0.0346 (12) | 0.0478 (13) | 0.0018 (11) | −0.0009 (12) | 0.0080 (10) |
C15 | 0.0297 (12) | 0.0367 (13) | 0.0499 (14) | −0.0004 (10) | −0.0015 (12) | 0.0004 (11) |
C21 | 0.0365 (13) | 0.0378 (13) | 0.0350 (12) | 0.0011 (11) | −0.0026 (11) | 0.0073 (10) |
C22 | 0.0310 (11) | 0.0355 (13) | 0.0299 (11) | −0.0011 (10) | 0.0003 (10) | 0.0011 (9) |
C23 | 0.0297 (11) | 0.0392 (13) | 0.0352 (11) | 0.0048 (10) | 0.0036 (10) | 0.0016 (10) |
C24 | 0.0409 (15) | 0.0496 (14) | 0.0359 (12) | −0.0013 (11) | 0.0071 (12) | 0.0060 (11) |
C25 | 0.0412 (15) | 0.0391 (13) | 0.0432 (13) | −0.0065 (12) | −0.0047 (12) | −0.0001 (10) |
O11—C10 | 1.375 (2) | C14—H141 | 0.9900 |
O11—C11 | 1.457 (2) | C14—H142 | 0.9900 |
O13—C10 | 1.403 (2) | C15—H151 | 0.9900 |
O13—C13 | 1.452 (2) | C15—H152 | 0.9900 |
O21—C10 | 1.389 (2) | C21—C22 | 1.498 (3) |
O21—C21 | 1.438 (3) | C21—H211 | 0.9900 |
O23—C10 | 1.401 (3) | C21—H212 | 0.9900 |
O23—C23 | 1.440 (2) | C22—C25 | 1.494 (3) |
C11—C12 | 1.494 (3) | C22—C24 | 1.495 (3) |
C11—H111 | 0.9900 | C22—C23 | 1.504 (3) |
C11—H112 | 0.9900 | C23—H231 | 0.9900 |
C12—C13 | 1.494 (3) | C23—H232 | 0.9900 |
C12—C14 | 1.495 (3) | C24—C25 | 1.503 (3) |
C12—C15 | 1.500 (3) | C24—H241 | 0.9900 |
C13—H131 | 0.9900 | C24—H242 | 0.9900 |
C13—H132 | 0.9900 | C25—H251 | 0.9900 |
C14—C15 | 1.509 (3) | C25—H252 | 0.9900 |
C10—O11—C11 | 112.96 (16) | C12—C15—H151 | 117.8 |
C10—O13—C13 | 112.74 (15) | C14—C15—H151 | 117.8 |
C10—O21—C21 | 112.81 (16) | C12—C15—H152 | 117.8 |
C10—O23—C23 | 113.24 (16) | C14—C15—H152 | 117.8 |
O11—C10—O21 | 104.80 (16) | H151—C15—H152 | 114.9 |
O11—C10—O23 | 107.41 (17) | O21—C21—C22 | 110.28 (19) |
O21—C10—O23 | 112.86 (17) | O21—C21—H211 | 109.6 |
O11—C10—O13 | 113.70 (17) | C22—C21—H211 | 109.6 |
O21—C10—O13 | 107.14 (15) | O21—C21—H212 | 109.6 |
O23—C10—O13 | 110.89 (17) | C22—C21—H212 | 109.6 |
O11—C11—C12 | 109.09 (17) | H211—C21—H212 | 108.1 |
O11—C11—H111 | 109.9 | C25—C22—C24 | 60.39 (16) |
C12—C11—H111 | 109.9 | C25—C22—C21 | 119.0 (2) |
O11—C11—H112 | 109.9 | C24—C22—C21 | 120.0 (2) |
C12—C11—H112 | 109.9 | C25—C22—C23 | 118.8 (2) |
H111—C11—H112 | 108.3 | C24—C22—C23 | 119.5 (2) |
C13—C12—C11 | 110.71 (19) | C21—C22—C23 | 111.0 (2) |
C13—C12—C14 | 120.2 (2) | O23—C23—C22 | 109.15 (18) |
C11—C12—C14 | 120.0 (2) | O23—C23—H231 | 109.9 |
C13—C12—C15 | 119.0 (2) | C22—C23—H231 | 109.9 |
C11—C12—C15 | 118.4 (2) | O23—C23—H232 | 109.9 |
C14—C12—C15 | 60.49 (16) | C22—C23—H232 | 109.9 |
O13—C13—C12 | 109.11 (17) | H231—C23—H232 | 108.3 |
O13—C13—H131 | 109.9 | C22—C24—C25 | 59.77 (15) |
C12—C13—H131 | 109.9 | C22—C24—H241 | 117.8 |
O13—C13—H132 | 109.9 | C25—C24—H241 | 117.8 |
C12—C13—H132 | 109.9 | C22—C24—H242 | 117.8 |
H131—C13—H132 | 108.3 | C25—C24—H242 | 117.8 |
C12—C14—C15 | 59.92 (15) | H241—C24—H242 | 114.9 |
C12—C14—H141 | 117.8 | C22—C25—C24 | 59.84 (16) |
C15—C14—H141 | 117.8 | C22—C25—H251 | 117.8 |
C12—C14—H142 | 117.8 | C24—C25—H251 | 117.8 |
C15—C14—H142 | 117.8 | C22—C25—H252 | 117.8 |
H141—C14—H142 | 114.9 | C24—C25—H252 | 117.8 |
C12—C15—C14 | 59.60 (15) | H251—C25—H252 | 114.9 |
C11—O11—C10—O21 | −172.98 (17) | C14—C12—C13—O13 | −158.8 (2) |
C11—O11—C10—O23 | 66.8 (2) | C15—C12—C13—O13 | −88.0 (2) |
C11—O11—C10—O13 | −56.3 (2) | C13—C12—C14—C15 | 108.4 (3) |
C21—O21—C10—O11 | −173.57 (17) | C11—C12—C14—C15 | −107.7 (3) |
C21—O21—C10—O23 | −57.0 (2) | C13—C12—C15—C14 | −110.3 (2) |
C21—O21—C10—O13 | 65.3 (2) | C11—C12—C15—C14 | 110.3 (2) |
C23—O23—C10—O11 | 172.79 (16) | C10—O21—C21—C22 | 54.1 (3) |
C23—O23—C10—O21 | 57.8 (2) | O21—C21—C22—C25 | 91.4 (2) |
C23—O23—C10—O13 | −62.4 (2) | O21—C21—C22—C24 | 162.05 (19) |
C13—O13—C10—O11 | 56.2 (2) | O21—C21—C22—C23 | −51.9 (3) |
C13—O13—C10—O21 | 171.48 (18) | C10—O23—C23—C22 | −54.5 (2) |
C13—O13—C10—O23 | −65.0 (2) | C25—C22—C23—O23 | −91.6 (2) |
C10—O11—C11—C12 | 54.8 (2) | C24—C22—C23—O23 | −161.94 (19) |
O11—C11—C12—C13 | −54.2 (3) | C21—C22—C23—O23 | 51.8 (3) |
O11—C11—C12—C14 | 158.8 (2) | C21—C22—C24—C25 | −108.4 (3) |
O11—C11—C12—C15 | 88.3 (2) | C23—C22—C24—C25 | 108.3 (2) |
C10—O13—C13—C12 | −54.3 (3) | C21—C22—C25—C24 | 110.0 (2) |
C11—C12—C13—O13 | 54.2 (3) | C23—C22—C25—C24 | −109.5 (2) |
Experimental details
Crystal data | |
Chemical formula | C11H16O4 |
Mr | 212.24 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 200 |
a, b, c (Å) | 6.2980 (8), 7.1520 (8), 23.508 (3) |
V (Å3) | 1058.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.19 × 0.10 |
Data collection | |
Diffractometer | Oxford XCalibur3 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6256, 1442, 1237 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.098, 1.08 |
No. of reflections | 1442 |
No. of parameters | 137 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.16, −0.17 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), CrysAlis RED, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.
O11—C10 | 1.375 (2) | O21—C10 | 1.389 (2) |
O13—C10 | 1.403 (2) | O23—C10 | 1.401 (3) |
O11—C10—O21 | 104.80 (16) | O21—C10—O13 | 107.14 (15) |
O11—C10—O23 | 107.41 (17) | O23—C10—O13 | 110.89 (17) |
O21—C10—O23 | 112.86 (17) | O11—C11—C12 | 109.09 (17) |
O11—C10—O13 | 113.70 (17) |
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The title compound, C11H16O4, a diol ester of the nonexistent orthocarbonic acid C(OH)4, was prepared for the purpose of collecting NMR data on orthocarbonates and for comparison with similar silicon compounds. It was obtained as the product of the reaction between dichlorodiphenoxymethane and 1,1-bis(hydroxymethyl)cyclopropane.
The molecular structure (Fig. 1) shows C2 symmetry. The 1,3-dioxane rings adopt chair conformations. The central carbon atom is in a distorted tetrahedral environment of four oxygen atoms. O11 and O21 are equatorial substituents, O13 and O23 are axial substituents, of their opposing six-membered rings. Due to the anomeric effect, the axial C10–O bonds are slightly, but significantly, longer than the corresponding equatorial bonds. The endocyclic O–C–O angles are significantly larger than the exocyclic ones.
The molecular packing is shown in Fig. 2.