4,4′-[Isopropyl­idenebis(p-phenyl­eneoxy)]dibutanoic acid

In the title compound, C₂₃H₂₈O₆, the mean planes of the two benzene rings make a dihedral angle of 81.1 (2)°. A twofold rotation axis passes through the central C atom. The mol­ecules are connected into chains via inter­molecular O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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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

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S1. Comment

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).

Related literature

For related literature, see: Ferguson et al. (1999); Staples et al. (1998).

S2. Experimental

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%.

S3. Refinement

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 U_iso(H) = 1.2U_eq(C) or 1.5U_eq(O).

Computing details

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).

Figures

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level for non-H atoms.
	Fig. 2. Detail of (I) showing part of a hydrogen-bonded chain. H atoms have been omitted for clarity and the dashed lines represent the O—H···O hydrogen bonds.

4,4'-[Isopropylidenebis(p-phenyleneoxy)]dibutanoic acid

Crystal data

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) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.22 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.9594P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (5)

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—C8^i	1.534 (2)
C3—H3A	0.970	C11—C12^i	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—C8^i	110.4 (2)
C2—C3—H3B	109.5	C8—C11—C12^i	111.51 (11)
H3A—C3—H3B	108.0	C8^i—C11—C12^i	107.70 (11)
O3—C4—C3	108.26 (17)	C8—C11—C12	107.70 (11)
O3—C4—H4A	110.0	C8^i—C11—C12	111.50 (11)
C3—C4—H4A	110.0	C12^i—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—C8^i	130.0 (2)
C4—O3—C5—C10	12.7 (3)	C9—C8—C11—C8^i	−52.07 (14)
C10—C5—C6—C7	−1.1 (3)	C7—C8—C11—C12^i	10.4 (3)
O3—C5—C6—C7	179.54 (18)	C9—C8—C11—C12^i	−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.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^ii	0.82	1.80	2.615 (2)	170

Symmetry code: (ii) −x, −y, −z.