Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042195/bi2236sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042195/bi2236Isup2.hkl |
CCDC reference: 663671
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.122
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a solution of bisphenol A (0.01 mol) in acetonitrile (50 ml), anhydrous potassium carbonate (0.02 mol) and ethyl 4-bromobutanoate were added (0.01 mol). The solution was refluxed for 6 h and then filtered. The filtrate was evaporated under reduced pressure and the residue was dissolved in water/ethanol (1:2 v/v), then sodium hydroxide (0.02 mol) was added. The solution was refluxed for 24 h, then acidified with dilute HCl. The crude product that precipitated was filtered off and crystals of the title compound (m.p. 458 K) were obtained by recrystallization from a mixture of water and ethanol (1:1). Elemental analysis calculated: C 68.98, H 7.05%; found: C 68.96, H 7.09%.
H atoms were placed in idealized locations with C—H = 0.93—0.97 Å or O—H = 0.82 Å and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Bisphenol A is an intermediate in the production of polycarbonate and epoxy resins, flame retardants, and other specialty products. It is moderately soluble and appears to be released into the environment through its use (Staples et al., 1998). Crystal engineering using bisphenol A derivatives has received attention (Ferguson et al., 1999). In the course of our studies on bisphenol A derivatives, we have synthesized and determined the structure of the title compound (Fig. 1). In the crystal, the mean planes of the two benzene rings make a dihedral angle of 81.1 (2) °. Intermolecular O—H···O hydrogen bonds link the molecules into chains (Fig. 2).
For related literature, see: Ferguson et al. (1999); Staples et al. (1998).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C23H28O6 | F(000) = 856 |
Mr = 400.45 | Dx = 1.254 Mg m−3 Dm = 1.254 Mg m−3 Dm measured by not measured |
Monoclinic, C2/c | Melting point: 458 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 17.7714 (6) Å | Cell parameters from 1720 reflections |
b = 6.4837 (2) Å | θ = 2.4–20.6° |
c = 18.9720 (7) Å | µ = 0.09 mm−1 |
β = 103.997 (1)° | T = 295 K |
V = 2121.13 (12) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.28 × 0.22 mm |
Bruker SMART CCD diffractometer | 1875 independent reflections |
Radiation source: fine-focus sealed tube | 1270 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
Tmin = 0.972, Tmax = 0.981 | k = −7→7 |
11585 measured reflections | l = −22→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.9594P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
1875 reflections | Δρmax = 0.16 e Å−3 |
135 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (5) |
C23H28O6 | V = 2121.13 (12) Å3 |
Mr = 400.45 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 17.7714 (6) Å | µ = 0.09 mm−1 |
b = 6.4837 (2) Å | T = 295 K |
c = 18.9720 (7) Å | 0.32 × 0.28 × 0.22 mm |
β = 103.997 (1)° |
Bruker SMART CCD diffractometer | 1875 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1270 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.981 | Rint = 0.043 |
11585 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.16 e Å−3 |
1875 reflections | Δρmin = −0.14 e Å−3 |
135 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 > 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.03166 (9) | 0.2268 (3) | 0.03972 (9) | 0.0870 (6) | |
O2 | 0.09455 (9) | −0.0031 (3) | −0.01063 (10) | 0.0840 (5) | |
H2 | 0.0521 | −0.0601 | −0.0193 | 0.126* | |
O3 | 0.23268 (7) | 0.7832 (2) | 0.13113 (8) | 0.0708 (5) | |
C1 | 0.09057 (12) | 0.1693 (3) | 0.02182 (11) | 0.0620 (6) | |
C2 | 0.16225 (12) | 0.2949 (3) | 0.03574 (12) | 0.0672 (6) | |
H2A | 0.1723 | 0.3322 | −0.0106 | 0.081* | |
H2B | 0.2051 | 0.2098 | 0.0613 | 0.081* | |
C3 | 0.16129 (12) | 0.4892 (3) | 0.07901 (12) | 0.0689 (6) | |
H3A | 0.1208 | 0.5803 | 0.0527 | 0.083* | |
H3B | 0.1497 | 0.4552 | 0.1251 | 0.083* | |
C4 | 0.23813 (12) | 0.5979 (3) | 0.09270 (12) | 0.0649 (6) | |
H4A | 0.2786 | 0.5105 | 0.1211 | 0.078* | |
H4B | 0.2509 | 0.6291 | 0.0470 | 0.078* | |
C5 | 0.29946 (10) | 0.8949 (3) | 0.15747 (10) | 0.0527 (5) | |
C6 | 0.29440 (12) | 1.0494 (3) | 0.20561 (12) | 0.0648 (6) | |
H6 | 0.2477 | 1.0734 | 0.2181 | 0.078* | |
C7 | 0.35832 (11) | 1.1692 (3) | 0.23550 (11) | 0.0601 (5) | |
H7 | 0.3538 | 1.2729 | 0.2681 | 0.072* | |
C8 | 0.42893 (10) | 1.1398 (3) | 0.21848 (10) | 0.0493 (5) | |
C9 | 0.43194 (11) | 0.9847 (3) | 0.16914 (11) | 0.0606 (6) | |
H9 | 0.4784 | 0.9611 | 0.1561 | 0.073* | |
C10 | 0.36848 (11) | 0.8637 (3) | 0.13856 (11) | 0.0576 (5) | |
H10 | 0.3725 | 0.7614 | 0.1053 | 0.069* | |
C11 | 0.5000 | 1.2749 (4) | 0.2500 | 0.0572 (7) | |
C12 | 0.51343 (13) | 1.4143 (3) | 0.18858 (14) | 0.0847 (8) | |
H12A | 0.5272 | 1.3309 | 0.1518 | 0.127* | |
H12B | 0.5547 | 1.5094 | 0.2078 | 0.127* | |
H12C | 0.4668 | 1.4895 | 0.1678 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0724 (10) | 0.0757 (11) | 0.1180 (14) | −0.0211 (8) | 0.0329 (10) | −0.0354 (10) |
O2 | 0.0712 (10) | 0.0739 (11) | 0.1062 (13) | −0.0166 (8) | 0.0202 (9) | −0.0331 (10) |
O3 | 0.0567 (9) | 0.0637 (9) | 0.0892 (11) | −0.0136 (7) | 0.0123 (7) | −0.0165 (8) |
C1 | 0.0641 (13) | 0.0555 (13) | 0.0629 (13) | −0.0108 (10) | 0.0081 (10) | −0.0081 (11) |
C2 | 0.0635 (13) | 0.0633 (14) | 0.0718 (14) | −0.0130 (10) | 0.0103 (11) | −0.0059 (11) |
C3 | 0.0648 (13) | 0.0631 (14) | 0.0747 (14) | −0.0158 (10) | 0.0090 (10) | −0.0088 (11) |
C4 | 0.0659 (13) | 0.0552 (13) | 0.0690 (13) | −0.0126 (10) | 0.0076 (10) | −0.0063 (11) |
C5 | 0.0496 (11) | 0.0476 (11) | 0.0558 (11) | −0.0034 (9) | 0.0029 (9) | 0.0008 (9) |
C6 | 0.0544 (12) | 0.0660 (14) | 0.0764 (14) | −0.0056 (10) | 0.0202 (10) | −0.0119 (12) |
C7 | 0.0605 (12) | 0.0524 (12) | 0.0663 (13) | −0.0005 (9) | 0.0133 (10) | −0.0108 (10) |
C8 | 0.0471 (10) | 0.0388 (10) | 0.0558 (11) | 0.0038 (8) | 0.0004 (8) | 0.0040 (9) |
C9 | 0.0474 (11) | 0.0545 (12) | 0.0778 (14) | 0.0019 (9) | 0.0112 (10) | −0.0102 (11) |
C10 | 0.0554 (11) | 0.0502 (12) | 0.0633 (13) | 0.0009 (9) | 0.0067 (9) | −0.0110 (10) |
C11 | 0.0531 (15) | 0.0379 (15) | 0.0730 (19) | 0.000 | 0.0003 (13) | 0.000 |
C12 | 0.0674 (14) | 0.0584 (14) | 0.116 (2) | −0.0015 (11) | −0.0012 (13) | 0.0348 (14) |
O1—C1 | 1.234 (2) | C6—C7 | 1.380 (3) |
O2—C1 | 1.286 (2) | C6—H6 | 0.930 |
O2—H2 | 0.820 | C7—C8 | 1.383 (3) |
O3—C5 | 1.377 (2) | C7—H7 | 0.930 |
O3—C4 | 1.421 (2) | C8—C9 | 1.384 (2) |
C1—C2 | 1.481 (3) | C8—C11 | 1.534 (2) |
C2—C3 | 1.506 (3) | C9—C10 | 1.381 (3) |
C2—H2A | 0.970 | C9—H9 | 0.930 |
C2—H2B | 0.970 | C10—H10 | 0.930 |
C3—C4 | 1.502 (3) | C11—C8i | 1.534 (2) |
C3—H3A | 0.970 | C11—C12i | 1.538 (3) |
C3—H3B | 0.970 | C11—C12 | 1.538 (3) |
C4—H4A | 0.970 | C12—H12A | 0.960 |
C4—H4B | 0.970 | C12—H12B | 0.960 |
C5—C6 | 1.373 (3) | C12—H12C | 0.960 |
C5—C10 | 1.374 (3) | ||
C1—O2—H2 | 109.5 | C5—C6—H6 | 119.9 |
C5—O3—C4 | 118.11 (15) | C7—C6—H6 | 119.9 |
O1—C1—O2 | 122.88 (19) | C6—C7—C8 | 122.01 (19) |
O1—C1—C2 | 122.4 (2) | C6—C7—H7 | 119.0 |
O2—C1—C2 | 114.8 (2) | C8—C7—H7 | 119.0 |
C1—C2—C3 | 115.76 (19) | C7—C8—C9 | 116.36 (17) |
C1—C2—H2A | 108.3 | C7—C8—C11 | 122.57 (16) |
C3—C2—H2A | 108.3 | C9—C8—C11 | 121.04 (16) |
C1—C2—H2B | 108.3 | C10—C9—C8 | 122.40 (18) |
C3—C2—H2B | 108.3 | C10—C9—H9 | 118.8 |
H2A—C2—H2B | 107.4 | C8—C9—H9 | 118.8 |
C4—C3—C2 | 110.92 (18) | C5—C10—C9 | 119.77 (18) |
C4—C3—H3A | 109.5 | C5—C10—H10 | 120.1 |
C2—C3—H3A | 109.5 | C9—C10—H10 | 120.1 |
C4—C3—H3B | 109.5 | C8—C11—C8i | 110.4 (2) |
C2—C3—H3B | 109.5 | C8—C11—C12i | 111.51 (11) |
H3A—C3—H3B | 108.0 | C8i—C11—C12i | 107.70 (11) |
O3—C4—C3 | 108.26 (17) | C8—C11—C12 | 107.70 (11) |
O3—C4—H4A | 110.0 | C8i—C11—C12 | 111.50 (11) |
C3—C4—H4A | 110.0 | C12i—C11—C12 | 108.0 (3) |
O3—C4—H4B | 110.0 | C11—C12—H12A | 109.5 |
C3—C4—H4B | 110.0 | C11—C12—H12B | 109.5 |
H4A—C4—H4B | 108.4 | H12A—C12—H12B | 109.5 |
C6—C5—C10 | 119.17 (17) | C11—C12—H12C | 109.5 |
C6—C5—O3 | 115.84 (17) | H12A—C12—H12C | 109.5 |
C10—C5—O3 | 124.99 (18) | H12B—C12—H12C | 109.5 |
C5—C6—C7 | 120.29 (18) | ||
O1—C1—C2—C3 | 5.1 (3) | C7—C8—C9—C10 | −0.5 (3) |
O2—C1—C2—C3 | −175.24 (19) | C11—C8—C9—C10 | −178.49 (18) |
C1—C2—C3—C4 | 177.26 (18) | C6—C5—C10—C9 | 1.3 (3) |
C5—O3—C4—C3 | 171.96 (17) | O3—C5—C10—C9 | −179.46 (18) |
C2—C3—C4—O3 | 177.79 (17) | C8—C9—C10—C5 | −0.5 (3) |
C4—O3—C5—C6 | −167.99 (18) | C7—C8—C11—C8i | 130.0 (2) |
C4—O3—C5—C10 | 12.7 (3) | C9—C8—C11—C8i | −52.07 (14) |
C10—C5—C6—C7 | −1.1 (3) | C7—C8—C11—C12i | 10.4 (3) |
O3—C5—C6—C7 | 179.54 (18) | C9—C8—C11—C12i | −171.74 (18) |
C5—C6—C7—C8 | 0.2 (3) | C7—C8—C11—C12 | −108.0 (2) |
C6—C7—C8—C9 | 0.6 (3) | C9—C8—C11—C12 | 69.9 (2) |
C6—C7—C8—C11 | 178.62 (18) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1ii | 0.82 | 1.80 | 2.615 (2) | 170 |
Symmetry code: (ii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C23H28O6 |
Mr | 400.45 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 17.7714 (6), 6.4837 (2), 18.9720 (7) |
β (°) | 103.997 (1) |
V (Å3) | 2121.13 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.972, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11585, 1875, 1270 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.04 |
No. of reflections | 1875 |
No. of parameters | 135 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.80 | 2.615 (2) | 169.8 |
Symmetry code: (i) −x, −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
Bisphenol A is an intermediate in the production of polycarbonate and epoxy resins, flame retardants, and other specialty products. It is moderately soluble and appears to be released into the environment through its use (Staples et al., 1998). Crystal engineering using bisphenol A derivatives has received attention (Ferguson et al., 1999). In the course of our studies on bisphenol A derivatives, we have synthesized and determined the structure of the title compound (Fig. 1). In the crystal, the mean planes of the two benzene rings make a dihedral angle of 81.1 (2) °. Intermolecular O—H···O hydrogen bonds link the molecules into chains (Fig. 2).