5,5′-Di-tert-butyl-2,2′-di­hydroxy-3,3′-methanediyl­dibenz­aldehyde and its allyl-protected dialcohol and di­aldehyde precursors

Goetz, S.; Barreira Fontecha, J.; McKee, V.

doi:10.1107/S010827010402089X

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 11| November 2004| Pages o776-o780

doi:10.1107/S010827010402089X

5,5′-Di-tert-butyl-2,2′-dihydroxy-3,3′-methanediyldibenzaldehyde and its allyl-protected dialcohol and dialdehyde precursors

Sandrine Goetz,^a Julia Barreira Fontecha ^a and Vickie McKee ^a ^*

^aChemistry Department, Loughborough University, Leicestershire LE11 3TU, England
^*Correspondence e-mail: v.mckee@lboro.ac.uk

(Received 9 August 2004; accepted 24 August 2004; online 9 October 2004)

5,5′-Di-tert-butyl-2,2′-dihydroxy-3,3′-methanediyldibenzaldehyde, C₂₃H₂₈O₄, (IV), has been structurally characterized in two polymorphic forms. The tetragonal form, (in I4₁/a) has been reported previously but is redetermined and reinterpreted here, while the monoclinic form, (in C2/c) is reported for the first time. In both polymorphs, the molecule lies on a crystallographic twofold axis. Two precursors in the synthesis of (IV), namely 2,2′-bis(allyloxy)-5,5′-di-tert-butyl-3,3′-methanediyldibenzenemethanol (C₂₉H₄₀O₄) and 2,2′-bis(allyloxy)-5,5′-di-tert-butyl-3,3′-methanediyldibenzaldehyde (C₂₉H₃₆O₄) have also been characterized.

Comment

The diphenolic dialdehyde 5,5′-di-tert-butyl-2,2′-dihydroxy- 3,3′-methanediyldibenzaldehyde, (IV), has been used to synthesize new polynucleating macrocycles by Schiff base condensation with diamines (Barreira Fontecha et al., 2002 ). Compound (IV) was prepared in three steps from the known dialcohol analogue 5,5′-di-tert-butyl-2,2′-dihydroxy-3,3′-methanediyldibenzenemethanol, (I) (Dhawan & Gutsche, 1983 ).

The structure of 2,2′-bis(allyloxy)-5,5′-di-tert-butyl-3,3′-methanediyldibenzenemethanol, (II), is shown in Fig. 1. The molecule is non-planar, with the two aryl rings inclined at 78.84 (9)° with respect to one another and the tert-butyl groups lying on opposite sides of the molecule. The apparent folding of the molecule is actually due to rotation about the C12—C4 and C12—C13 bonds, and the conformation adopted is probably a consequence of the hydrogen-bonding network throughout the lattice. Hydrogen bonding between alcohol groups generates eight-membered rings [graph-set notation R₄⁴(8)] and links the molecules into a double chain running parallel to the a axis (Fig. 2 and Table 1). The H atoms on the hydroxy groups are disordered, and these atoms were modelled with 50% occupancy of two equivalent positions. As a result there are two self-consistent hydrogen-bonding patterns, which have O—H⋯O directions running either anticlockwise (as in Fig. 2) or clockwise around the same ring. The highest residual electron-density peak is 1.26 Å from atom C28 and 1.39 Å from atom C27, and may indicate a minor disorder of that allyl group.

The dialcohol was oxidized using MnO₂ to form the analogous dialdehyde, 2,2′-bis(allyloxy)-5,5′-di-tert-butyl-3,3′-methanediyldibenzaldehyde, (III). As Fig. 3 shows, the phenyl planes are inclined at 74.17 (5)° and the tert-butyl groups are on the same side of the molecule. One of the allyl groups is disordered, and this disorder was modelled as a 70:30 occupancy of two conformations. Again, the molecules are linked by hydrogen bonding into a double chain, in this case running parallel to c (Fig. 4); however, the interactions are all of the type C—H⋯O=C (Table 2). There is also some π–π stacking across the hydrogen-bonded chain involving the benzaldehyde groups. The section incorporating atoms O1/C1/C2/C3/C7 overlaps the O4/C23/C16–C18 section of a neighbouring molecule at (x, $[1\over2]$ − y, $[1\over2]$ + z). The planes of the interacting benzaldehyde rings are inclined at 12.33 (7)°, while atoms O1 and C1 are 3.274 (2) and 3.357 (2) Å, respectively, from the mean plane of the interacting phenyl ring (Fig. 4).

Compound (IV) has been characterized in two polymorphic forms. We obtained the tetragonal form, (IVa) (space group I4₁/a), by recrystallization of the crude material from diethyl ether, while Masci et al. (2004 ) obtained the same polymorph by recrystallization from methanol. A second polymorph was formed as a side product in the synthesis of a macrocyclic complex; crystals of (IVb) in the monoclinic space group C2/c were obtained from a methanol solution containing 1,5-diaminopentan-3-ol and nickel(II) nitrate.

In the tetragonal form, (IVa), the asymmetric unit contains half of the molecule, with a twofold axis passing through atom C12 (Fig. 5), while in the monoclinic form, (IVb), the asymmetric unit contains two independent half molecules, each having twofold symmetry (Fig. 6). The molecular conformation and bond lengths are similar in the two polymorphs; the tert-butyl groups are on opposite sides of the linked aryl rings and the phenol H atoms are involved in intramolecular hydrogen bonds with the adjacent carbonyl groups (Tables 3 and 4). In (IVb), there is additional intermolecular hydrogen bonding involving one of the carbonyl groups (C13=O3). Atom C13 forms a C—H⋯O=C hydrogen bond to atom O3 of a neighbouring molecule at (−x, 2 − y, 1 − z), resulting in zigzag chains parallel to c. The second molecule does not show a corresponding interaction. As in the precursors, the phenyl rings are inclined with respect to one another: in the tetragonal form, the phenyl rings are inclined at 61.48 (5)°, whereas in the monoclinic polymorph, the values are 73.58 (5) and 75.04 (5)°.

In form (IVa), the molecules are packed as shown in Figs. 5 and 7. In contrast to the previous report of this structure (Masci et al., 2004), we have identified π–π interactions (the most direct overlap being between the sections containing atoms O1/C1/C2/C7/C6; see Fig. 5) linking the molecules into sets of zigzag ribbons running parallel to either the a or the b axis. As can be seen in Fig. 5, π-stacked pairs of rings are parallel and related by inversion; the distance between the mean plane of the benzaldehyde ring containing atoms O1 and C7 and the centroid of the neighbouring phenyl ring at (2 − x, 1 − y, −z) is 3.361 (4) Å.

In polymorph (IVb), the two independent molecules form ABAB π-stacked columns parallel to the b axis (Fig. 8). The relative rotation between adjacent layers prevents steric interference between successive tert-butyl groups (Fig. 6). The benzaldehyde rings are almost parallel [interplanar angle = 6.34 (10)°], with average interplanar separations of 3.48 and 3.32 Å between the ring containing atoms O1 and C7 and that containing O3 and C19 at (−x, y, $[1 \over 2]$ − z) and (−x, 1 + y, $[1\over2]$ − z), respectively. Again, the shortest π–π interactions are between the carbonyl groups and the phenyl rings of neighbouring molecules in the stack.

Figure 1
A view of the structure of (II

). The H atoms on the two alcohol functions are disordered and only one position is shown for each. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
The hydrogen bonding in (II

), producing a double chain parallel to a. Only one of the two orientations of the hydrogen bonding within the R₄⁴(8) ring is shown. [Symmetry codes: (i) 1 + x, y, z; (ii) −x, 2 − y, −z; (iii) 1 − x, 2 − y, −z.]

Figure 3
A view of the structure of (III

), showing the disorder in one allyl group. Displacement ellipsoids are drawn at the 50% probability level.

Figure 4
The C—H⋯O=C hydrogen-bonded chain parallel to b in (III

). [Symmetry codes: (vi) x, $[1\over 2]$ − y, $[1\over 2]$ + z; (vii) x, $[1\over 2]$ − y, − $[1\over 2]$ + z.]

Figure 5
A view of the structure of polymorph (IVa); intramolecular hydrogen-bonding interactions between the phenol and aldehyde functions are shown as dashed lines. Dotted lines show interatomic distances in the range 3.42–3.47 Å in the π–π overlap region. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (viii) 2 − x, $[3\over 2]$ − y, z; (ix) 2 − x, 1 − y, −z.]

Figure 6
A view of the two independent molecules in polymorph (IVb). A twofold axis passes through atoms C12 and C24. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (x) −x, y, $[1\over2]$ − z.]

Figure 7
A unit-cell plot for polymorph (IVa), viewed down the a axis, showing the π–π-stacked ribbons running parallel to a and parallel to b. O atoms are shown as shaded circles. Dashed lines indicate the π–π overlapped sections.

Figure 8
A unit-cell plot for polymorph (IVb), projected down b, showing π-stacked columns parallel to b and inter- and intramolecular hydrogen bonding (dashed lines). O atoms are shown as shaded circles.

Experimental

Compound (I) was synthesized according to the procedure of Dhawan & Gutsche (1983). For the synthesis of (II), compound (I) (10 g, 27 mmol), allyl bromide (7 g, 58 mmol), anhydrous K₂CO₃ (7.42 g) and acetone (100 ml) were placed in a 250 ml three-necked round-bottomed flask fitted with a reflux condenser and a sealed stirrer unit, and were refluxed for 20 h with stirring. The reaction mixture was then poured into water (200 ml) and the aqueous layer was extracted three times with diethyl ether. The organic layer was washed with a 2 M sodium hydroxide solution and dried over anhydrous K₂CO₃. The solvent was removed under vacuum, leaving a white solid, which was recrystallized from dichloromethane/n-hexane; the yield was 9.0 g (74%). Colourless crystals suitable for X-ray studies were obtained by slow evaporation of a solution of dichloromethane/pentane (1:5). Thin-layer chromatography (TLC) on silica gel (diethyl ether/petroleum ether 40/60, 45:55): R_F = 0.68. Analysis calculated for (II)·0.5H₂O: C 75.45, H 8.95%; found: C 75.64, H 9.06%. ¹H NMR (CDCl₃, p.p.m.): 7.24 (d, 2H, ArH), 7.01 (d, 2H, ArH), 6.07 (m, 2H, allyl =CH), 5.34 (dd, 2H, allyl =CH₂), 5.30 (dd, 2H, allyl =CH₂), 4.73 (d, 4H, CH₂OH), 4.34 (d, 4H, allyl CH₂), 4.70 (s, 4H, CH₂OH), 4.07 (s, 2H, ArCH₂Ar), 1.26 [s, 18H, C(CH₃)₃]. IR (KBr, cm⁻¹): 3272 [s, ν(OH)], 3081 [w, ν(allyl =CH₂)], 883 (m, 1,2,3,5 tetrasubstitution of Ar).

Compound (III) was synthesized by a method similar to that reported by Taniguchi (1984 ). Activated MnO₂ (50 g) was added to a solution of (II) (9 g, 20 mmol) in chloroform (200 ml). The reaction mixture was refluxed for 19–20 h, after which time MnO₂ was filtered off and the organic layer dried over anhydrous MgSO₄. The solvent was removed under vacuum, leaving a pale-yellow oil that crystallized under vacuum over a period of one week. The solid was then washed with cold methanol to remove the yellow impurities. Colourless crystals suitable for X-ray studies were obtained by slow evaporation of a diethyl ether solution of the product. The yield was 7.0 g (78%). TLC on silica gel (diethyl ether/petroleum ether 40/60, 30:70): R_F = 0.50. Analysis calculated for (III)·0.5H₂O: C 76.11, H 8.15%; found: C 76.08, H 8.15%. ¹H NMR (CDCl₃, p.p.m.): 10.4 (s, 2H, CHO), 7.75 (d, 2H, ArH), 7.30 (d, 2H, ArH), 6.06 (m, 2H, allyl =CH), 4.40 (dd, 2H, allyl =CH₂), 4.44 (dd, 2H, allyl =CH₂), 4.13 (s, 2H, ArCH₂Ar), 1.26 [s, 18H, C(CH₃)₃]. IR (KBr, cm⁻¹): 1660 [ν(C=O)], 3081 [w, ν(allyl =CH₂)], 885 (m, 1,2,3,5 tetrasubstitution of Ar).

Compound (IV) was obtained using the method described by Boss & Scheffold (1976 ). To a solution of (III) (7 g, 15.6 mmol) in ethanol (150 ml) were added 10% Pd on activated charcoal (1.5 g) and p-toluenesulfonic acid (0.7 g) in water (5 ml). The stirred suspension was refluxed for 2 d, after which time the reaction mixture was filtered hot. On cooling, the product precipitated out as a pale-yellow powder, which was filtered off (yield 1 g). An additional portion of (IV) (3 g) was obtained on concentration of the resulting filtrate. Pale-yellow crystals of (IVa) suitable for X-ray studies were obtained by slow evaporation from a solution of the product in diethyl ether. The yield was 4 g (70%). TLC on silica gel (diethyl ether/petroleum ether 40/60, 30:70): R_F = 0.64. Analysis calculated: C 74.97, H 7.66%; found: C 74.51, H 7.86%. ¹H NMR (CDCl₃, p.p.m.): 11.19 (s, 2H, Ar—OH), 9.86 (s, 2H, CHO), 7.64 (d, 2H, ArH), 7.37 (d, 2H, ArH), 4.03 (s, 2H, ArCH₂Ar), 1.26 [s, 18H, C(CH₃)₃]. IR (KBr, cm⁻¹): 1658 [ν(C=O)], 1270 [s, ν(ArOH)], 1216 (s).

Compound (II)

Crystal data

C₂₉H₄₀O₄
M_r = 452.61
Triclinic, $[P\overline 1]$
a = 10.6025 (11) Å
b = 11.9199 (12) Å
c = 12.4180 (13) Å
α = 64.611 (2)°
β = 82.672 (2)°
γ = 66.330 (2)°
V = 1296.7 (2) Å³
Z = 2
D_x = 1.159 Mg m⁻³
Mo Kα radiation
Cell parameters from 2476 reflections
θ = 2.3–27.2°
μ = 0.08 mm⁻¹
T = 150 (2) K
Block, colourless
0.29 × 0.17 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.938, T_max = 1.000
9408 measured reflections
4565 independent reflections
3085 reflections with I > 2σ(I)
R_int = 0.025
θ_max = 25.0°
h = −12 → 12
k = −14 → 14
l = −14 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.173
S = 1.04
4565 reflections
310 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0843P)² + 0.7234P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bonding geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1OA⋯O4ⁱ	0.83	1.93	2.744 (3)	166
O1—H1OB⋯O4^iv	0.82	1.99	2.749 (2)	155
O4—H4OA⋯O1^iv	0.91	1.85	2.749 (2)	167
O4—H4OB⋯O1^v	0.84	1.90	2.744 (3)	177
Symmetry codes: (i) 1+x,y,z; (iv) -x,1-y,-z; (v) x-1,y,z.

Compound (III)

Crystal data

C₂₉H₃₆O₄
M_r = 448.58
Monoclinic, P2₁/c
a = 16.2931 (10) Å
b = 10.1951 (6) Å
c = 16.4318 (10) Å
β = 108.367 (1)°
V = 2590.4 (3) Å³
Z = 4
D_x = 1.150 Mg m⁻³
Mo Kα radiation
Cell parameters from 7890 reflections
θ = 2.4–23.3°
μ = 0.08 mm⁻¹
T = 150 (2) K
Block, colourless
0.26 × 0.16 × 0.14 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.900, T_max = 1.000
17 928 measured reflections
4559 independent reflections
3620 reflections with I > 2σ(I)
R_int = 0.020
θ_max = 25.0°
h = −19 → 19
k = −12 → 12
l = −19 → 19

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.02
4559 reflections
317 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.058P)² + 1.0861P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 2
Hydrogen-bonding geometry (Å, °) for (III)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1^vii	0.95	2.46	3.406 (2)	171
C14—H14⋯O4^vi	0.95	2.62	3.560 (2)	170
Symmetry codes: (vi) $[x,{\script{1\over 2}}-y,{\script{1\over 2}}+z]$ ; (vii) $[x,{\script{1\over 2}}-y,-{\script{1\over 2}}+z]$ .

Polymorph (IVa)

Crystal data

C₂₃H₂₈O₄
M_r = 368.45
Tetragonal, I4₁/a
a = 12.7930 (7) Å
c = 24.158 (2) Å
V = 3953.7 (4) Å³
Z = 8
D_x = 1.238 Mg m⁻³
Mo Kα radiation
Cell parameters from 3205 reflections
θ = 2.8–22.8°
μ = 0.08 mm⁻¹
T = 150 (2) K
Tablet, yellow
0.28 × 0.20 × 0.05 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.931, T_max = 1.000
19 093 measured reflections
1736 independent reflections
1203 reflections with I > 2σ(I)
R_int = 0.056
θ_max = 25.0°
h = −15 → 15
k = −15 → 15
l = −28 → 28

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.120
S = 1.04
1736 reflections
125 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0446P)² + 4.6694P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 3
Hydrogen-bonding geometry (Å, °) for (IVa)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.92 (2)	1.80 (2)	2.645 (2)	151 (2)

Polymorph (IVb)

Crystal data

C₂₃H₂₈O₄
M_r = 368.45
Monoclinic, C2/c
a = 26.809 (2) Å
b = 8.4543 (7) Å
c = 21.3720 (18) Å
β = 120.618 (1)°
V = 4168.7 (6) Å³
Z = 8
D_x = 1.174 Mg m⁻³
Mo Kα radiation
Cell parameters from 3051 reflections
θ = 2.6–25.6°
μ = 0.08 mm⁻¹
T = 153 (2) K
Tablet, light brown
0.48 × 0.38 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.919, T_max = 1.000
14 739 measured reflections
3668 independent reflections
2235 reflections with I > 2σ(I)
R_int = 0.049
θ_max = 25.0°
h = −31 → 31
k = −10 → 10
l = −25 → 25

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.01
3668 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0393P)² + 4.8718P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 4
Hydrogen-bonding geometry (Å, °) for (IVb)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.94 (2)	1.81 (2)	2.625 (3)	144 (2)
O4—H4⋯O3	0.88 (2)	1.85 (2)	2.631 (2)	147 (2)
C13—H13⋯O3ⁱⁱ	0.95	2.57	3.454 (3)	156
Symmetry code: (ii) -x,2-y,1-z.

Except as described below, H atoms bonded to C atoms were placed at calculated positions and refined using a riding model. The constrained C—H distances were 0.95, 0.98, 0.99 and 0.99 Å for aryl, methyl, methylene and ethylene H atoms, respectively. The U_iso(H) values were set at 1.2U_eq(C) for methylene and aryl H atoms, and at 1.5U_eq(C) for tert-butyl H atoms. For (II), the disordered H atoms bonded to atoms O1 and O4 were located from difference maps and were not further refined; their U_iso(H) values were fixed at 0.04 Å². The U_iso(H) values of the tert-butyl H atoms were fixed at 0.05 Å², and those of the H atoms on atoms C27 and C24 at 0.04 Å². For (IVa), H atoms bonded to O atoms were placed at calculated positions, with a constrained O—H distance of 0.84 Å and with U_iso(H) set at 1.5U_eq of the carrier O atom. In (IVb), the U_iso values for the tert-butyl H atoms were fixed at 0.05 Å², while the phenol H atoms were located from difference maps and their positions refined, with U_iso(H) values fixed at 0.05 Å².

For all determinations, data collection: SMART (Bruker, 1998 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks II, III, IVa, IVb, global. DOI: 10.1107/S010827010402089X/bm1580sup1.cif

Structure factors: contains datablock II. DOI: 10.1107/S010827010402089X/bm1580IIsup2.hkl

Structure factors: contains datablock III. DOI: 10.1107/S010827010402089X/bm1580IIIsup3.hkl

Structure factors: contains datablock IVa. DOI: 10.1107/S010827010402089X/bm1580IVasup4.hkl

Structure factors: contains datablock IVb. DOI: 10.1107/S010827010402089X/bm1580IVbsup5.hkl

Comment top

The diphenolic dialdehyde 5,5'-di-tert-butyl-2,2'-dihydroxy- 3,3'-methanediyldibenzaldehyde, (IV), has been used to synthesize new polynucleating macrocycles by Schiff base condensation with diamines (Barreira Fontecha et al., 2002). Compound (IV) was prepared in three steps from the known dialcohol analogue 5,5'-di-tert-butyl-2,2'-dihydroxy- 3,3'-methanediyldibenzenemethanol, (I) (Dhawan & Gutsche, 1983).

The structure of 2,2'-bis(allyloxy)-5,5'-di-tert-butyl-3,3'-methanediyldibenzenemethanol, (II), is shown in Fig. 1. The molecule is non-planar, with the two aryl rings inclined at 78.84 (9)° with respect to one another and the tert-butyl groups lying on opposite sides of the molecule. The apparent folding of the molecule is actually due to rotation about the C12—C4 and C12—C13 bonds, and the conformation adopted is probably a consequence of the hydrogen-bonding network throughout the lattice. Hydrogen bonding between alcohol groups generates eight-membered rings [graph set notation R₄⁴(8)] and links the molecules into a double chain running parallel to the a axis (Fig. 2 and Table 1). The H atoms on the hydroxy groups are disordered, and these atoms were modelled with 50% occupancy of two equivalent positions. The highest residual electron density peak (0.69 e Å⁻³) is 1.26 (s.u.?) Å from C28 and 1.39 (s.u.?) Å from C27, and may indicate a minor disorder of that allyl group.

The dialcohol was oxidized using MnO₂ to form the analogous dialdehyde 2,2'-bis(allyloxy)-5,5'-di-tert-butyl-3,3'-methanediyldibenzaldehyde, (III). As Fig. 3 shows, the phenyl planes are inclined at 74.17 (5)° and the tert-butyl groups are on the same side of the molecule. One of the allyl groups is disordered, and this disorder was modelled as 70:30 occupancy of two conformations. Again, the molecules are linked by hydrogen bonding into a double chain, in this case running parallel to c (Fig. 4); however, the interactions are all of the type C—H····O═C (Table 2). There is also some π–π stacking across the hydrogen-bonded chain involving the benzaldehyde groups. The section incorporating atoms O1, C1, C2, C3 and C7 overlaps the O4/C23/C16–C18 section of a neighbouring molecule under symmetry operation (x, 0.5 − y, 0.5 + z). The planes of the interacting benzaldehyde rings are inclined at 12.33 (7)°, while atoms O1 and C1 are 3.274 (2) and 3.357 (2) Å, respectively, from the mean plane of the interacting phenyl ring (Fig. 4).

Compound (IV) has been characterized in two polymorphic forms. We obtained the tetragonal form, (IVa) (space group I4₁/a), by recrystallization of the crude material from diethyl ether, while Masci et al. (2004) obtained the same polymorph by recrystallization from methanol. A second polymorph was formed as a side product in the synthesis of a macrocyclic complex; crystals of (IVb) in the monoclinic space group C2/c were obtained from a methanol solution containing 1,5-diaminopentan-3-ol and nickel(II) nitrate.

In the tetragonal form, (IVa), the asymmetric unit contains half of the molecule, with a twofold axis passing through C12 (Fig. 5), while in the monoclinic form, (IVb), the asymmetric unit contains two independent half molecules, each having twofold symmetry (Fig. 6). The molecular conformation and bond lengths are similar in the two polymorphs; the tert-butyl groups are on opposite sides of the linked aryl rings and the phenol H atoms are involved in intramolecular hydrogen bonds with the adjacent carbonyl groups (Tables 3 and 4). In (IVb), there is additional intermolecular hydrogen bonding involving one of the carbonyl groups (C13═O3). Atom C13 forms a C—H····O═C hydrogen bond to atom O3 of a neighbouring molecule at (-x, 2 − y, 1 − z), resulting in zigzag chains parallel to c. The second molecule does not show a corresponding interaction. As in the precursors, the phenyl rings are inclined with respect to one another. In the tetragonal form, the phenyl rings are inclined at 61.48 (5)°, whereas in the monoclinic polymorph, the values are 73.58 (5) and 75.04 (5)°.

In form (IVa), the molecules are packed as shown in Figs. 5 and 7. In contrast to the previous report of this structure (Masci et al., 2004), we have identified π–π interactions (the most direct overlap being between the sections containing atoms O1, C1, C2, C7 and C6; see Fig. 5) linking the molecules into sets of zigzag ribbons running parallel to either the a or the b axis. π stacked pairs of rings are parallel and related by inversion; the distance between the mean plane of the benzaldehyde ring containing atoms O1 and C7 and the centroid of the neighbouring phenyl ring at (2 − x, 1 − y, −z) is 3.361 (4) Å.

In polymorph (IVb), the two independent molecules form ABAB π stacked columns parallel to the b axis (Fig. 8). The relative rotation between adjacent layers prevents steric interference between successive tert-butyl groups (Fig. 6). The benzaldehyde rings are almost parallel [interplanar angle 6.3 (s.u.?)°], with average interplanar separations of 3.48 and 3.32 Å between the ring containing atoms O1 and C7 and that containing O3 and C19 at (-x, y, 0.5 − z) and (-x, 1 + y, 0.5 − z), respectively. Again, the shortest π–π interactions are between the carbonyl groups and the phenyl rings of neighbouring molecules in the stack.

Experimental top

Compound (I) was synthesized according to the procedure of Dhawan & Gutsche (1982).

For the synthesis of (II), compound (I) (10 g, 27 mmol), allylbromide (7 g, 58 mmol), anhydrous K₂CO₃ (7.42 g) and acetone (100 ml) were placed in a 250 ml three-necked round-bottomed flask fitted with a reflux condenser and sealed stirrer unit, and were refluxed for 20 h with stirring. The reaction mixture was then poured into water (200 ml) and the aqueous layer was extracted three times with diethyl ether. The organic layer was washed with a 2M sodium hydroxide solution and dried over anhydrous K₂CO₃. The solvent was removed under vacuum, leaving a white solid, which was recrystallized from dichloromethane/n-hexane. The yield was 9.0 g (74%). Colourless crystals suitable for X-ray studies were obtained by slow evaporation of a solution of dichloromethane/ pentane (1:5). Thin-layer chromatography (TLC) on silica gel (diethylether/pet–ether 40/60, 45:55) Rf = 0.68. Analysis calculated for (II)·0.5H₂O: C 75.45, H 8.95%; found: C 75.64, H 9.06%. ¹H NMR (CDCl₃, p.p.m.): 7.24 (d, 2, ArH), 7.01 (d, 2, ArH), 6.07 (m, 2, allyl ═CH), 5.34 (dd, 2, allyl ═CH₂), 5.30 (dd, 2, allyl ═CH₂), 4.73 (d, 4, CH₂OH), 4.34 (d, 4, allyl CH₂), 4.70 (s, 4, CH₂OH), 4.07 (s, 2, ArCH₂Ar), 1.26 (s, 18, C(CH₃)₃). IR (KBr, cm⁻¹): 3272 (s, ν_OH), 3081 (w, ν_allyl_═_CH2), 883 (m, 1,2,3,5 tetrasubstitution of Ar).

Compound (III) was synthesized by a method similar to that reported by Taniguchi (1984). Activated MnO₂ (50 g) was added to a solution of (II) (9 g, 20 mmol) in chloroform (200 ml). The reaction mixture was refluxed for 19–20 h, after which time MnO₂ was filtered off and the organic layer was dried over anhydrous MgSO₄. The solvent was removed under vacuum, leaving a pale-yellow oil that crystallized under vacuum over a week. The solid was then washed with cold methanol to remove the yellow impurities. Colourless crystals suitable for X-ray studies were obtained by slow evaporation of a diethyl ether solution of the product. The yield is 7.0 g (78%). TLC on silica gel (diethylether/ pet–ether 40/60, 30:70) Rf = 0.50. Analysis calculated for (III)·0.5H₂O: C 76.11, H 8.15%; found: C 76.08, H 8.15%. ¹H NMR (CDCl₃, p.p.m.): 10.4 (s, 2,CHO), 7.75 (d, 2, ArH), 7.30 (d, 2, ArH), 6.06 (m, 2, allyl ═CH), 4.40 (dd, 2, allyl ═CH₂), 4.44 (dd, 2, allyl ═CH₂), 4.13 (s, 2, ArCH₂Ar), 1.26 (s, 18, C(CH₃)₃). IR (KBr, cm⁻¹): 1660 (ν_C_═_O), 3081 (w, ν_allyl_═_CH2), 885 (m, 1,2,3,5 tetrasubstitution of Ar).

Compound (IV) was obtained using the method described by Boss & Scheffold (1976). To a solution of (III) (7 g, 15.6 mmol) in ethanol (150 ml) were added 10% Pd on activated charcoal (1.5 g) and p-toluenesulfonic acid (0.7 g) in water (5 ml). The stirred suspension was refluxed for 2 d, after which time the reaction mixture was filtered hot. On cooling, the product precipitated out as a pale-yellow powder, which was filtered off (yield 1 g). An additional portion of (IV) (3 g) was obtained on concentration of the resulting filtrate. Pale-yellow crystals of (IVa) suitable for X-ray studies were obtained by slow evaporation from a solution of the product in diethyl ether. The yield was 4 g (70%). TLC on silica gel (diethylether/pet–ether 40/60, 30:70) Rf = 0.64. Analysis calculated: C 74.97, H 7.66%; found: C 74.51, H 7.86%. ¹H NMR (CDCl₃, p.p.m.): 11.19 (s, 2H, Ar–OH), 9.86 (s, 2, CHO), 7.64 (d, 2, ArH), 7.37 (d, 2, ArH), 4.03 (s, 2, ArCH₂Ar), 1.26 [s, 18, C(CH₃)₃]. IR (KBr, cm⁻¹): 1658 (ν_C_═_O), 1270 (s, ν_(ArOH)), 1216 (s).

##AUTHOR: Would "tablet" be better than "block" for the crystal shape of IVa, ## given that there is one dimensions much smaller than the other two?

Computing details top

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the structure of (II). The H atoms on the two alcohol functions are disordered, and only one position is shown. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The hydrogen bonding in (II), leading to a double chain parallel to a. [Symmetry codes: (i) 1 + x, y, z; (ii) −x, 2 − y, −z; (iii) = 1 − x, 2 − y, −z.]
	Fig. 3. A view of the structure of (III), showing the disorder in one allyl group. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. The C—H···O═C hydrogen-bonded chain parallel to b in (III). [Symmetry codes: (i) x, 0.5 − y, 0.5 + z; (ii) x, 0.5 − y, −0.5 + z.]
	Fig. 5. A view of the structure of (IVa); intramolecular hydrogen-bonding interactions between the phenol and aldehyde functions are shown as dashed lines. Dotted lines show interatomic distances in the range 3.42–3.47 Å in the π–π overlap region. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 2 − x, 1.5 − y, z, (ii) 2 − x, 1 − y, −z.]
	Fig. 6. A view of the two independent molecules in (IVb). A twofold axis passes through atoms C12 and C24. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) −x, y, 0.5 − z.]
	Fig. 7. A unit cell plot for (IVa), viewed down the a axis, showing the π–π stacked ribbons running parallel to a and parallel to b. O atoms are shown as shaded circles. Dashed lines indicate the π–π overlapped sections.
	Fig. 8. A unit-cell plot for (IVb), projected down b, showing π stacked columns parallel to b and inter- and intramolecular hydrogen bonding (dashed lines). O atoms are shown as shaded circles.

(II) 2,2'-bis(allyloxy)-5,5'-di-tert-butyl-3,3'-methanediyldibenzenemethanol top

Crystal data top

C₂₉H₄₀O₄	Z = 2
M_r = 452.61	F(000) = 492
Triclinic, P1	D_x = 1.159 Mg m⁻³
a = 10.6025 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9199 (12) Å	Cell parameters from 2476 reflections
c = 12.4180 (13) Å	θ = 2.3–27.2°
α = 64.611 (2)°	µ = 0.08 mm⁻¹
β = 82.672 (2)°	T = 150 K
γ = 66.330 (2)°	Block, colourless
V = 1296.7 (2) Å³	0.29 × 0.17 × 0.12 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4565 independent reflections
Radiation source: normal-focus sealed tube	3085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −12→12
T_min = 0.938, T_max = 1.000	k = −14→14
9408 measured reflections	l = −14→14

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0843P)² + 0.7234P] where P = (F_o² + 2F_c²)/3
4565 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₉H₄₀O₄	γ = 66.330 (2)°
M_r = 452.61	V = 1296.7 (2) Å³
Triclinic, P1	Z = 2
a = 10.6025 (11) Å	Mo Kα radiation
b = 11.9199 (12) Å	µ = 0.08 mm⁻¹
c = 12.4180 (13) Å	T = 150 K
α = 64.611 (2)°	0.29 × 0.17 × 0.12 mm
β = 82.672 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4565 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3085 reflections with I > 2σ(I)
T_min = 0.938, T_max = 1.000	R_int = 0.025
9408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.04	Δρ_max = 0.69 e Å⁻³
4565 reflections	Δρ_min = −0.22 e Å⁻³
310 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.34147 (18)	0.45442 (18)	0.04311 (17)	0.0350 (5)
C1	0.2100 (3)	0.4894 (3)	−0.0094 (2)	0.0274 (6)
H1A	0.1918	0.5682	−0.0874	0.033*
H1B	0.1356	0.5131	0.0434	0.033*
C2	0.2132 (2)	0.3708 (2)	−0.0259 (2)	0.0223 (5)
C3	0.1642 (2)	0.2774 (2)	0.0588 (2)	0.0221 (5)
O2	0.10499 (17)	0.29559 (17)	0.15977 (15)	0.0272 (4)
C4	0.1704 (2)	0.1654 (2)	0.0439 (2)	0.0221 (5)
C5	0.2330 (2)	0.1468 (2)	−0.0561 (2)	0.0231 (5)
H5	0.2392	0.0703	−0.0664	0.028*
C6	0.2872 (2)	0.2354 (2)	−0.1417 (2)	0.0227 (5)
C7	0.2738 (2)	0.3479 (2)	−0.1249 (2)	0.0245 (6)
H7	0.3072	0.4114	−0.1831	0.029*
C8	0.3584 (3)	0.2077 (3)	−0.2485 (2)	0.0293 (6)
C9	0.2579 (3)	0.1980 (4)	−0.3195 (3)	0.0512 (9)
H9A	0.3038	0.1799	−0.3873	0.077*
H9B	0.1772	0.2832	−0.3488	0.077*
H9C	0.2284	0.1248	−0.2677	0.077*
C10	0.4841 (3)	0.0739 (3)	−0.2021 (3)	0.0471 (8)
H10A	0.5304	0.0556	−0.2697	0.071*
H10B	0.4540	0.0010	−0.1506	0.071*
H10C	0.5483	0.0797	−0.1563	0.071*
C11	0.4082 (4)	0.3183 (4)	−0.3318 (3)	0.0555 (9)
H11A	0.4536	0.2968	−0.3983	0.083*
H11B	0.4737	0.3243	−0.2875	0.083*
H11C	0.3291	0.4047	−0.3629	0.083*
C12	0.1130 (2)	0.0662 (2)	0.1340 (2)	0.0232 (5)
H12A	0.1572	0.0321	0.2135	0.028*
H12B	0.1396	−0.0114	0.1131	0.028*
C13	−0.0424 (2)	0.1213 (2)	0.1433 (2)	0.0223 (5)
C14	−0.0995 (2)	0.1238 (2)	0.2502 (2)	0.0239 (6)
H14	−0.0393	0.0936	0.3161	0.029*
C15	−0.2413 (3)	0.1690 (2)	0.2644 (2)	0.0255 (6)
C16	−0.3253 (3)	0.2084 (2)	0.1666 (2)	0.0266 (6)
H16	−0.4223	0.2378	0.1741	0.032*
C17	−0.2736 (2)	0.2066 (2)	0.0586 (2)	0.0235 (5)
C18	−0.1309 (2)	0.1654 (2)	0.0469 (2)	0.0227 (5)
O3	−0.07517 (17)	0.15992 (17)	−0.05911 (14)	0.0262 (4)
C19	−0.3047 (3)	0.1796 (3)	0.3797 (2)	0.0291 (6)
C20	−0.4174 (4)	0.1242 (5)	0.4156 (3)	0.0669 (11)
H20A	−0.4561	0.1320	0.4892	0.100*
H20B	−0.3785	0.0292	0.4288	0.100*
H20C	−0.4903	0.1755	0.3518	0.100*
C21	−0.1966 (3)	0.1030 (4)	0.4847 (2)	0.0553 (9)
H21A	−0.2412	0.1130	0.5560	0.083*
H21B	−0.1248	0.1399	0.4646	0.083*
H21C	−0.1548	0.0074	0.5003	0.083*
C22	−0.3634 (4)	0.3278 (3)	0.3585 (3)	0.0570 (10)
H22A	−0.4037	0.3366	0.4314	0.086*
H22B	−0.4348	0.3801	0.2933	0.086*
H22C	−0.2893	0.3617	0.3370	0.086*
C23	−0.3723 (3)	0.2521 (2)	−0.0429 (2)	0.0273 (6)
H23A	−0.3207	0.2207	−0.1037	0.033*
H23B	−0.4411	0.2104	−0.0125	0.033*
O4	−0.44276 (18)	0.39600 (17)	−0.09784 (16)	0.0323 (5)
C24	0.0170 (4)	0.3774 (4)	0.3440 (3)	0.0750 (13)
H24A	−0.0451	0.4117	0.2783	0.090*
H24B	−0.0134	0.4027	0.4086	0.090*
C25	0.1415 (4)	0.2974 (4)	0.3455 (3)	0.0510 (9)
H25	0.1991	0.2663	0.4134	0.061*
C26	0.2058 (3)	0.2478 (3)	0.2528 (2)	0.0358 (7)
H26A	0.2811	0.2796	0.2185	0.043*
H26B	0.2461	0.1481	0.2894	0.043*
C27	−0.2187 (4)	0.3605 (4)	−0.3517 (3)	0.0665 (11)
H27A	−0.2885	0.4338	−0.3393	0.080*
H27B	−0.2238	0.3480	−0.4214	0.080*
C28	−0.1153 (3)	0.2768 (3)	−0.2729 (3)	0.0437 (8)
H28	−0.0468	0.2043	−0.2874	0.052*
C29	−0.0998 (3)	0.2897 (3)	−0.1610 (2)	0.0325 (6)
H29A	−0.0214	0.3166	−0.1660	0.039*
H29B	−0.1845	0.3598	−0.1508	0.039*
H1OA	0.3973	0.4354	−0.0060	0.040*	0.50
H1OB	0.3456	0.5127	0.0594	0.040*	0.50
H4OA	−0.3960	0.4349	−0.0782	0.040*	0.50
H4OB	−0.5073	0.4132	−0.0527	0.040*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0306 (10)	0.0334 (11)	0.0489 (12)	−0.0147 (9)	−0.0023 (9)	−0.0206 (9)
C1	0.0243 (13)	0.0265 (14)	0.0338 (14)	−0.0101 (11)	0.0010 (11)	−0.0141 (12)
C2	0.0192 (12)	0.0231 (13)	0.0248 (13)	−0.0069 (10)	−0.0009 (10)	−0.0107 (11)
C3	0.0172 (12)	0.0281 (13)	0.0210 (12)	−0.0062 (10)	0.0015 (10)	−0.0126 (11)
O2	0.0252 (9)	0.0351 (10)	0.0263 (9)	−0.0119 (8)	0.0055 (7)	−0.0179 (8)
C4	0.0169 (12)	0.0262 (13)	0.0240 (13)	−0.0081 (10)	0.0000 (10)	−0.0110 (11)
C5	0.0211 (12)	0.0227 (13)	0.0254 (13)	−0.0073 (10)	−0.0010 (10)	−0.0105 (11)
C6	0.0186 (12)	0.0250 (13)	0.0205 (12)	−0.0056 (10)	−0.0006 (10)	−0.0081 (10)
C7	0.0241 (13)	0.0251 (13)	0.0243 (13)	−0.0118 (11)	0.0024 (10)	−0.0084 (11)
C8	0.0322 (14)	0.0328 (15)	0.0253 (14)	−0.0130 (12)	0.0070 (11)	−0.0153 (12)
C9	0.0503 (19)	0.075 (2)	0.0376 (17)	−0.0219 (18)	0.0052 (15)	−0.0346 (17)
C10	0.0416 (18)	0.0493 (19)	0.0433 (18)	−0.0079 (15)	0.0106 (14)	−0.0241 (16)
C11	0.079 (3)	0.057 (2)	0.0386 (18)	−0.0352 (19)	0.0284 (17)	−0.0254 (16)
C12	0.0222 (13)	0.0219 (13)	0.0234 (13)	−0.0077 (11)	0.0018 (10)	−0.0084 (10)
C13	0.0229 (13)	0.0175 (12)	0.0252 (13)	−0.0085 (10)	0.0021 (10)	−0.0073 (10)
C14	0.0247 (13)	0.0230 (13)	0.0213 (13)	−0.0105 (11)	0.0010 (10)	−0.0055 (10)
C15	0.0280 (14)	0.0212 (13)	0.0247 (13)	−0.0109 (11)	0.0048 (11)	−0.0069 (11)
C16	0.0221 (13)	0.0248 (13)	0.0305 (14)	−0.0099 (11)	0.0051 (11)	−0.0096 (11)
C17	0.0243 (13)	0.0193 (12)	0.0270 (13)	−0.0096 (10)	0.0004 (10)	−0.0083 (11)
C18	0.0270 (13)	0.0193 (12)	0.0240 (13)	−0.0104 (11)	0.0032 (10)	−0.0101 (10)
O3	0.0289 (10)	0.0273 (10)	0.0230 (9)	−0.0096 (8)	0.0028 (7)	−0.0128 (8)
C19	0.0291 (14)	0.0295 (14)	0.0248 (14)	−0.0112 (12)	0.0075 (11)	−0.0098 (11)
C20	0.073 (3)	0.116 (3)	0.054 (2)	−0.069 (3)	0.0407 (19)	−0.052 (2)
C21	0.0484 (19)	0.069 (2)	0.0240 (16)	−0.0070 (17)	0.0065 (14)	−0.0137 (16)
C22	0.085 (3)	0.0399 (19)	0.0326 (17)	−0.0137 (18)	0.0187 (17)	−0.0165 (15)
C23	0.0232 (13)	0.0263 (14)	0.0327 (14)	−0.0091 (11)	−0.0001 (11)	−0.0125 (11)
O4	0.0310 (10)	0.0283 (10)	0.0362 (11)	−0.0106 (8)	−0.0063 (8)	−0.0108 (8)
C24	0.066 (3)	0.093 (3)	0.059 (2)	−0.001 (2)	−0.001 (2)	−0.051 (2)
C25	0.062 (2)	0.061 (2)	0.0325 (17)	−0.0170 (18)	−0.0015 (15)	−0.0259 (16)
C26	0.0363 (16)	0.0427 (17)	0.0277 (14)	−0.0124 (13)	−0.0020 (12)	−0.0155 (13)
C27	0.082 (3)	0.081 (3)	0.0354 (19)	−0.037 (2)	−0.0150 (19)	−0.0131 (19)
C28	0.0496 (19)	0.0470 (19)	0.0339 (16)	−0.0201 (16)	0.0041 (14)	−0.0156 (14)
C29	0.0355 (15)	0.0301 (15)	0.0281 (14)	−0.0122 (12)	0.0003 (12)	−0.0089 (12)

Geometric parameters (Å, º) top

O1—C1	1.440 (3)	C15—C19	1.535 (3)
O1—H1OA	0.8329	C16—C17	1.388 (3)
O1—H1OB	0.8200	C16—H16	0.9500
C1—C2	1.500 (3)	C17—C18	1.399 (3)
C1—H1A	0.9900	C17—C23	1.508 (3)
C1—H1B	0.9900	C18—O3	1.389 (3)
C2—C3	1.391 (3)	O3—C29	1.464 (3)
C2—C7	1.395 (3)	C19—C20	1.520 (4)
C3—O2	1.392 (3)	C19—C22	1.529 (4)
C3—C4	1.399 (3)	C19—C21	1.539 (4)
O2—C26	1.436 (3)	C20—H20A	0.9800
C4—C5	1.392 (3)	C20—H20B	0.9800
C4—C12	1.513 (3)	C20—H20C	0.9800
C5—C6	1.393 (3)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C6—C7	1.394 (3)	C21—H21C	0.9800
C6—C8	1.536 (3)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C11	1.529 (4)	C22—H22C	0.9800
C8—C9	1.533 (4)	C23—O4	1.437 (3)
C8—C10	1.534 (4)	C23—H23A	0.9900
C9—H9A	0.9800	C23—H23B	0.9900
C9—H9B	0.9800	O4—H4OA	0.9127
C9—H9C	0.9800	O4—H4OB	0.8446
C10—H10A	0.9800	C24—C25	1.278 (5)
C10—H10B	0.9800	C24—H24A	0.9500
C10—H10C	0.9800	C24—H24B	0.9500
C11—H11A	0.9800	C25—C26	1.483 (4)
C11—H11B	0.9800	C25—H25	0.9500
C11—H11C	0.9800	C26—H26A	0.9900
C12—C13	1.519 (3)	C26—H26B	0.9900
C12—H12A	0.9900	C27—C28	1.309 (4)
C12—H12B	0.9900	C27—H27A	0.9500
C13—C18	1.393 (3)	C27—H27B	0.9500
C13—C14	1.394 (3)	C28—C29	1.498 (4)
C14—C15	1.395 (3)	C28—H28	0.9500
C14—H14	0.9500	C29—H29A	0.9900
C15—C16	1.393 (3)	C29—H29B	0.9900

C1—O1—H1OA	103.6	C17—C16—C15	122.9 (2)
C1—O1—H1OB	114.1	C17—C16—H16	118.5
H1OA—O1—H1OB	114.6	C15—C16—H16	118.5
O1—C1—C2	108.52 (19)	C16—C17—C18	118.5 (2)
O1—C1—H1A	110.0	C16—C17—C23	119.3 (2)
C2—C1—H1A	110.0	C18—C17—C23	122.2 (2)
O1—C1—H1B	110.0	O3—C18—C13	119.1 (2)
C2—C1—H1B	110.0	O3—C18—C17	120.2 (2)
H1A—C1—H1B	108.4	C13—C18—C17	120.6 (2)
C3—C2—C7	118.4 (2)	C18—O3—C29	116.10 (18)
C3—C2—C1	121.8 (2)	C20—C19—C22	110.3 (3)
C7—C2—C1	119.7 (2)	C20—C19—C15	111.0 (2)
C2—C3—O2	120.1 (2)	C22—C19—C15	108.2 (2)
C2—C3—C4	121.4 (2)	C20—C19—C21	108.2 (3)
O2—C3—C4	118.5 (2)	C22—C19—C21	106.8 (3)
C3—O2—C26	112.68 (18)	C15—C19—C21	112.2 (2)
C5—C4—C3	117.8 (2)	C19—C20—H20A	109.5
C5—C4—C12	120.8 (2)	C19—C20—H20B	109.5
C3—C4—C12	121.4 (2)	H20A—C20—H20B	109.5
C4—C5—C6	122.9 (2)	C19—C20—H20C	109.5
C4—C5—H5	118.5	H20A—C20—H20C	109.5
C6—C5—H5	118.5	H20B—C20—H20C	109.5
C5—C6—C7	116.9 (2)	C19—C21—H21A	109.5
C5—C6—C8	120.6 (2)	C19—C21—H21B	109.5
C7—C6—C8	122.5 (2)	H21A—C21—H21B	109.5
C6—C7—C2	122.5 (2)	C19—C21—H21C	109.5
C6—C7—H7	118.8	H21A—C21—H21C	109.5
C2—C7—H7	118.8	H21B—C21—H21C	109.5
C11—C8—C9	108.9 (2)	C19—C22—H22A	109.5
C11—C8—C10	108.2 (2)	C19—C22—H22B	109.5
C9—C8—C10	109.3 (2)	H22A—C22—H22B	109.5
C11—C8—C6	111.8 (2)	C19—C22—H22C	109.5
C9—C8—C6	109.7 (2)	H22A—C22—H22C	109.5
C10—C8—C6	108.9 (2)	H22B—C22—H22C	109.5
C8—C9—H9A	109.5	O4—C23—C17	112.0 (2)
C8—C9—H9B	109.5	O4—C23—H23A	109.2
H9A—C9—H9B	109.5	C17—C23—H23A	109.2
C8—C9—H9C	109.5	O4—C23—H23B	109.2
H9A—C9—H9C	109.5	C17—C23—H23B	109.2
H9B—C9—H9C	109.5	H23A—C23—H23B	107.9
C8—C10—H10A	109.5	C23—O4—H4OA	109.5
C8—C10—H10B	109.5	C23—O4—H4OB	104.6
H10A—C10—H10B	109.5	H4OA—O4—H4OB	93.5
C8—C10—H10C	109.5	C25—C24—H24A	120.0
H10A—C10—H10C	109.5	C25—C24—H24B	120.0
H10B—C10—H10C	109.5	H24A—C24—H24B	120.0
C8—C11—H11A	109.5	C24—C25—C26	127.1 (3)
C8—C11—H11B	109.5	C24—C25—H25	116.5
H11A—C11—H11B	109.5	C26—C25—H25	116.5
C8—C11—H11C	109.5	O2—C26—C25	110.4 (2)
H11A—C11—H11C	109.5	O2—C26—H26A	109.6
H11B—C11—H11C	109.5	C25—C26—H26A	109.6
C4—C12—C13	115.50 (19)	O2—C26—H26B	109.6
C4—C12—H12A	108.4	C25—C26—H26B	109.6
C13—C12—H12A	108.4	H26A—C26—H26B	108.1
C4—C12—H12B	108.4	C28—C27—H27A	120.0
C13—C12—H12B	108.4	C28—C27—H27B	120.0
H12A—C12—H12B	107.5	H27A—C27—H27B	120.0
C18—C13—C14	118.5 (2)	C27—C28—C29	123.2 (3)
C18—C13—C12	120.8 (2)	C27—C28—H28	118.4
C14—C13—C12	120.6 (2)	C29—C28—H28	118.4
C13—C14—C15	122.8 (2)	O3—C29—C28	108.9 (2)
C13—C14—H14	118.6	O3—C29—H29A	109.9
C15—C14—H14	118.6	C28—C29—H29A	109.9
C16—C15—C14	116.6 (2)	O3—C29—H29B	109.9
C16—C15—C19	120.6 (2)	C28—C29—H29B	109.9
C14—C15—C19	122.8 (2)	H29A—C29—H29B	108.3

O1—C1—C2—C3	94.7 (3)	C18—C13—C14—C15	−0.2 (4)
O1—C1—C2—C7	−81.6 (3)	C12—C13—C14—C15	−177.7 (2)
C7—C2—C3—O2	179.0 (2)	C13—C14—C15—C16	2.0 (4)
C1—C2—C3—O2	2.7 (3)	C13—C14—C15—C19	−176.4 (2)
C7—C2—C3—C4	−2.3 (3)	C14—C15—C16—C17	−1.4 (4)
C1—C2—C3—C4	−178.5 (2)	C19—C15—C16—C17	177.0 (2)
C2—C3—O2—C26	−83.1 (3)	C15—C16—C17—C18	−1.0 (4)
C4—C3—O2—C26	98.2 (3)	C15—C16—C17—C23	−179.5 (2)
C2—C3—C4—C5	2.8 (3)	C14—C13—C18—O3	−178.3 (2)
O2—C3—C4—C5	−178.4 (2)	C12—C13—C18—O3	−0.8 (3)
C2—C3—C4—C12	−178.0 (2)	C14—C13—C18—C17	−2.3 (3)
O2—C3—C4—C12	0.7 (3)	C12—C13—C18—C17	175.2 (2)
C3—C4—C5—C6	−1.0 (3)	C16—C17—C18—O3	178.8 (2)
C12—C4—C5—C6	179.9 (2)	C23—C17—C18—O3	−2.7 (3)
C4—C5—C6—C7	−1.3 (3)	C16—C17—C18—C13	2.9 (3)
C4—C5—C6—C8	178.5 (2)	C23—C17—C18—C13	−178.6 (2)
C5—C6—C7—C2	1.9 (3)	C13—C18—O3—C29	−112.4 (2)
C8—C6—C7—C2	−177.8 (2)	C17—C18—O3—C29	71.6 (3)
C3—C2—C7—C6	−0.2 (3)	C16—C15—C19—C20	46.1 (3)
C1—C2—C7—C6	176.2 (2)	C14—C15—C19—C20	−135.6 (3)
C5—C6—C8—C11	179.2 (2)	C16—C15—C19—C22	−75.1 (3)
C7—C6—C8—C11	−1.0 (3)	C14—C15—C19—C22	103.2 (3)
C5—C6—C8—C9	58.4 (3)	C16—C15—C19—C21	167.3 (3)
C7—C6—C8—C9	−121.9 (3)	C14—C15—C19—C21	−14.4 (4)
C5—C6—C8—C10	−61.3 (3)	C16—C17—C23—O4	75.1 (3)
C7—C6—C8—C10	118.5 (3)	C18—C17—C23—O4	−103.3 (3)
C5—C4—C12—C13	−114.7 (2)	C3—O2—C26—C25	166.8 (2)
C3—C4—C12—C13	66.2 (3)	C24—C25—C26—O2	−3.8 (5)
C4—C12—C13—C18	63.8 (3)	C18—O3—C29—C28	−145.7 (2)
C4—C12—C13—C14	−118.7 (2)	C27—C28—C29—O3	129.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OB···O4ⁱ	0.82	1.99	2.749 (2)	155
O1—H1OA···O4ⁱⁱ	0.83	1.93	2.744 (3)	166
O4—H4OA···O1ⁱ	0.91	1.85	2.749 (2)	167
O4—H4OB···O1ⁱⁱⁱ	0.84	1.90	2.744 (3)	177

Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) x−1, y, z.

(III) 2,2'-bis(allyloxy)-5,5'-di-tert-butyl-3,3'-methanediyldibenzaldehyde top

Crystal data top

C₂₉H₃₆O₄	F(000) = 968
M_r = 448.58	D_x = 1.150 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.2931 (10) Å	Cell parameters from 7890 reflections
b = 10.1951 (6) Å	θ = 2.4–23.3°
c = 16.4318 (10) Å	µ = 0.08 mm⁻¹
β = 108.367 (1)°	T = 150 K
V = 2590.4 (3) Å³	Block, pale yellow
Z = 4	0.26 × 0.16 × 0.14 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4559 independent reflections
Radiation source: normal-focus sealed tube	3620 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −19→19
T_min = 0.900, T_max = 1.000	k = −12→12
17928 measured reflections	l = −19→19

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.058P)² + 1.0861P] where P = (F_o² + 2F_c²)/3
4559 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₉H₃₆O₄	V = 2590.4 (3) Å³
M_r = 448.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.2931 (10) Å	µ = 0.08 mm⁻¹
b = 10.1951 (6) Å	T = 150 K
c = 16.4318 (10) Å	0.26 × 0.16 × 0.14 mm
β = 108.367 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4559 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3620 reflections with I > 2σ(I)
T_min = 0.900, T_max = 1.000	R_int = 0.020
17928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
4559 reflections	Δρ_min = −0.18 e Å⁻³
317 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.63607 (10)	0.33380 (15)	1.08524 (9)	0.0608 (4)
O4	0.86478 (9)	0.34770 (14)	0.45857 (8)	0.0534 (4)
C1	0.67472 (13)	0.38088 (19)	1.04065 (11)	0.0462 (5)
H1	0.7123	0.4526	1.0628	0.055*
C2	0.66705 (10)	0.33351 (16)	0.95351 (10)	0.0342 (4)
C3	0.70349 (10)	0.40326 (15)	0.90068 (10)	0.0317 (4)
C4	0.69296 (9)	0.36070 (15)	0.81739 (10)	0.0288 (3)
C5	0.64915 (9)	0.24344 (16)	0.79061 (10)	0.0310 (4)
H5	0.6429	0.2128	0.7344	0.037*
C6	0.61386 (9)	0.16860 (16)	0.84255 (10)	0.0323 (4)
C7	0.62221 (10)	0.21718 (17)	0.92370 (10)	0.0351 (4)
H7	0.5969	0.1704	0.9598	0.042*
C8	0.56911 (11)	0.03898 (18)	0.80846 (12)	0.0428 (4)
C9	0.52995 (14)	−0.0256 (2)	0.87163 (14)	0.0608 (6)
H9A	0.5015	−0.1078	0.8471	0.091*
H9B	0.4874	0.0336	0.8828	0.091*
H9C	0.5758	−0.0441	0.9255	0.091*
C10	0.49717 (13)	0.0616 (2)	0.72365 (12)	0.0570 (5)
H10A	0.4690	−0.0221	0.7022	0.085*
H10B	0.5219	0.0989	0.6816	0.085*
H10C	0.4544	0.1226	0.7328	0.085*
C11	0.63634 (14)	−0.0536 (2)	0.79162 (18)	0.0707 (7)
H11A	0.6087	−0.1370	0.7689	0.106*
H11B	0.6830	−0.0694	0.8454	0.106*
H11C	0.6603	−0.0134	0.7498	0.106*
C12	0.72087 (10)	0.44424 (16)	0.75498 (11)	0.0342 (4)
H12A	0.7519	0.5218	0.7861	0.041*
H12B	0.6684	0.4764	0.7104	0.041*
C13	0.77824 (9)	0.37788 (14)	0.71076 (9)	0.0272 (3)
C14	0.83411 (9)	0.27642 (14)	0.74857 (9)	0.0273 (3)
H14	0.8350	0.2463	0.8036	0.033*
C15	0.88930 (9)	0.21633 (15)	0.70929 (10)	0.0291 (3)
C16	0.88543 (10)	0.26107 (15)	0.62858 (10)	0.0307 (3)
H16	0.9225	0.2230	0.6005	0.037*
C17	0.82869 (10)	0.36046 (15)	0.58740 (10)	0.0302 (3)
C18	0.77561 (9)	0.41923 (14)	0.62884 (10)	0.0285 (3)
C19	0.94943 (10)	0.10569 (16)	0.75587 (11)	0.0358 (4)
C20	1.00889 (12)	0.05833 (19)	0.70575 (12)	0.0476 (5)
H20A	1.0459	−0.0126	0.7375	0.071*
H20B	1.0451	0.1313	0.6984	0.071*
H20C	0.9737	0.0261	0.6494	0.071*
C21	1.00683 (11)	0.1551 (2)	0.84346 (11)	0.0465 (5)
H21A	0.9703	0.1866	0.8767	0.070*
H21B	1.0433	0.2271	0.8352	0.070*
H21C	1.0435	0.0833	0.8744	0.070*
C22	0.89451 (13)	−0.00976 (18)	0.76842 (14)	0.0501 (5)
H22A	0.8563	0.0197	0.8004	0.075*
H22B	0.9325	−0.0795	0.8005	0.075*
H22C	0.8596	−0.0434	0.7123	0.075*
C23	0.82405 (11)	0.40009 (17)	0.49972 (11)	0.0392 (4)
H23	0.7869	0.4708	0.4741	0.047*
O2	0.74638 (8)	0.52087 (11)	0.92911 (7)	0.0401 (3)
C24	0.84626 (18)	0.7420 (2)	0.93001 (16)	0.0698 (7)
H24A	0.7858	0.7440	0.9009	0.084*
H24B	0.8796	0.8198	0.9350	0.084*
C25	0.88268 (15)	0.6348 (2)	0.96244 (14)	0.0573 (5)
H25	0.9432	0.6375	0.9910	0.069*
C26	0.83900 (13)	0.50676 (19)	0.95959 (15)	0.0577 (6)
H26A	0.8572	0.4464	0.9213	0.069*
H26B	0.8568	0.4678	1.0177	0.069*
O3	0.71578 (7)	0.51227 (10)	0.58584 (7)	0.0357 (3)
C27	0.6204 (3)	0.8014 (4)	0.5349 (3)	0.0694 (10)	0.70
H27A	0.6445	0.8179	0.4902	0.083*	0.70
H27B	0.5682	0.8436	0.5344	0.083*	0.70
C28	0.6583 (3)	0.7218 (4)	0.5960 (3)	0.0572 (9)	0.70
H28	0.6312	0.7092	0.6389	0.069*	0.70
C29	0.73933 (12)	0.64767 (16)	0.60730 (12)	0.0444 (4)	0.70
H29A	0.7704	0.6834	0.5692	0.053*	0.70
H29B	0.7776	0.6545	0.6674	0.053*	0.70
C27'	0.6173 (11)	0.7853 (16)	0.5874 (11)	0.113 (5)	0.30
H27C	0.6230	0.7673	0.6456	0.136*	0.30
H27D	0.5724	0.8411	0.5545	0.136*	0.30
C28'	0.6708 (5)	0.7338 (8)	0.5528 (7)	0.0506 (19)	0.30
H28'	0.6662	0.7506	0.4947	0.061*	0.30
C29'	0.73933 (12)	0.64767 (16)	0.60730 (12)	0.0444 (4)	0.30
H29C	0.7951	0.6672	0.5977	0.053*	0.30
H29D	0.7462	0.6635	0.6685	0.053*	0.30

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0847 (10)	0.0650 (9)	0.0419 (7)	0.0187 (8)	0.0331 (7)	0.0085 (7)
O4	0.0657 (9)	0.0631 (9)	0.0403 (7)	−0.0012 (7)	0.0293 (7)	0.0014 (6)
C1	0.0606 (12)	0.0427 (10)	0.0356 (9)	0.0168 (9)	0.0158 (9)	0.0044 (8)
C2	0.0355 (8)	0.0363 (9)	0.0302 (8)	0.0101 (7)	0.0093 (7)	0.0024 (7)
C3	0.0300 (8)	0.0286 (8)	0.0345 (8)	0.0064 (7)	0.0072 (7)	−0.0006 (7)
C4	0.0233 (7)	0.0316 (8)	0.0324 (8)	0.0063 (6)	0.0100 (6)	0.0023 (7)
C5	0.0253 (8)	0.0377 (9)	0.0292 (8)	0.0035 (7)	0.0077 (6)	−0.0024 (7)
C6	0.0225 (7)	0.0363 (9)	0.0365 (9)	0.0022 (6)	0.0070 (7)	0.0021 (7)
C7	0.0303 (8)	0.0409 (9)	0.0358 (9)	0.0062 (7)	0.0128 (7)	0.0090 (7)
C8	0.0337 (9)	0.0420 (10)	0.0498 (10)	−0.0076 (8)	0.0092 (8)	−0.0008 (8)
C9	0.0595 (13)	0.0555 (13)	0.0609 (13)	−0.0213 (10)	0.0099 (10)	0.0109 (10)
C10	0.0489 (11)	0.0653 (13)	0.0498 (11)	−0.0255 (10)	0.0056 (9)	−0.0017 (10)
C11	0.0572 (13)	0.0431 (12)	0.109 (2)	−0.0097 (10)	0.0217 (13)	−0.0260 (12)
C12	0.0342 (8)	0.0317 (9)	0.0400 (9)	0.0062 (7)	0.0165 (7)	0.0034 (7)
C13	0.0243 (7)	0.0261 (8)	0.0309 (8)	−0.0034 (6)	0.0084 (6)	−0.0014 (6)
C14	0.0255 (7)	0.0292 (8)	0.0276 (7)	−0.0019 (6)	0.0089 (6)	0.0010 (6)
C15	0.0252 (7)	0.0295 (8)	0.0329 (8)	−0.0017 (6)	0.0095 (6)	−0.0010 (6)
C16	0.0295 (8)	0.0321 (8)	0.0336 (8)	−0.0019 (7)	0.0144 (7)	−0.0047 (7)
C17	0.0316 (8)	0.0294 (8)	0.0293 (8)	−0.0065 (6)	0.0091 (7)	−0.0014 (6)
C18	0.0257 (7)	0.0254 (8)	0.0314 (8)	−0.0034 (6)	0.0046 (6)	−0.0002 (6)
C19	0.0335 (8)	0.0368 (9)	0.0401 (9)	0.0075 (7)	0.0158 (7)	0.0050 (7)
C20	0.0442 (10)	0.0514 (11)	0.0510 (11)	0.0208 (9)	0.0204 (9)	0.0065 (9)
C21	0.0377 (9)	0.0572 (12)	0.0416 (10)	0.0153 (9)	0.0085 (8)	0.0071 (9)
C22	0.0515 (11)	0.0352 (10)	0.0674 (13)	0.0097 (8)	0.0244 (10)	0.0117 (9)
C23	0.0450 (10)	0.0392 (9)	0.0340 (9)	−0.0080 (8)	0.0135 (8)	−0.0002 (7)
O2	0.0458 (7)	0.0293 (6)	0.0416 (7)	0.0021 (5)	0.0086 (5)	−0.0048 (5)
C24	0.0963 (18)	0.0447 (12)	0.0846 (17)	−0.0022 (12)	0.0518 (15)	0.0034 (12)
C25	0.0648 (13)	0.0463 (12)	0.0629 (13)	−0.0108 (10)	0.0232 (11)	−0.0115 (10)
C26	0.0475 (11)	0.0402 (11)	0.0708 (14)	−0.0048 (9)	−0.0022 (10)	−0.0021 (10)
O3	0.0379 (6)	0.0285 (6)	0.0364 (6)	0.0024 (5)	0.0055 (5)	0.0039 (5)
C27	0.060 (2)	0.0344 (18)	0.103 (3)	0.0072 (17)	0.011 (2)	0.008 (2)
C28	0.076 (3)	0.0338 (18)	0.074 (3)	0.0125 (16)	0.041 (2)	0.0073 (19)
C29	0.0538 (11)	0.0277 (9)	0.0513 (11)	−0.0033 (8)	0.0161 (9)	0.0038 (8)
C27'	0.145 (12)	0.088 (9)	0.138 (13)	0.024 (8)	0.091 (11)	0.042 (9)
C28'	0.060 (5)	0.036 (4)	0.063 (5)	0.004 (4)	0.029 (4)	0.010 (4)
C29'	0.0538 (11)	0.0277 (9)	0.0513 (11)	−0.0033 (8)	0.0161 (9)	0.0038 (8)

Geometric parameters (Å, º) top

O1—C1	1.206 (2)	C16—H16	0.9500
O4—C23	1.211 (2)	C17—C18	1.394 (2)
C1—C2	1.479 (2)	C17—C23	1.475 (2)
C1—H1	0.9500	C18—O3	1.3839 (18)
C2—C3	1.392 (2)	C19—C22	1.531 (2)
C2—C7	1.398 (2)	C19—C21	1.534 (2)
C3—O2	1.3923 (19)	C19—C20	1.534 (2)
C3—C4	1.394 (2)	C20—H20A	0.9800
C4—C5	1.391 (2)	C20—H20B	0.9800
C4—C12	1.509 (2)	C20—H20C	0.9800
C5—C6	1.397 (2)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C6—C7	1.388 (2)	C21—H21C	0.9800
C6—C8	1.528 (2)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.528 (3)	C22—H22C	0.9800
C8—C10	1.530 (3)	C23—H23	0.9500
C8—C11	1.535 (3)	O2—C26	1.440 (2)
C9—H9A	0.9800	C26—C25	1.481 (3)
C9—H9B	0.9800	C26—H26A	0.9900
C9—H9C	0.9800	C26—H26B	0.9900
C10—H10A	0.9800	C25—C24	1.277 (3)
C10—H10B	0.9800	C25—H25	0.9500
C10—H10C	0.9800	C24—H24A	0.9500
C11—H11A	0.9800	C24—H24B	0.9500
C11—H11B	0.9800	O3—C29	1.446 (2)
C11—H11C	0.9800	C29—C28	1.481 (5)
C12—C13	1.513 (2)	C29—H29A	0.9900
C12—H12A	0.9900	C29—H29B	0.9900
C12—H12B	0.9900	C28—C27	1.289 (6)
C13—C14	1.389 (2)	C28—H28	0.9500
C13—C18	1.398 (2)	C27—H27A	0.9500
C14—C15	1.402 (2)	C27—H27B	0.9500
C14—H14	0.9500	C28'—C27'	1.291 (17)
C15—C16	1.385 (2)	C28'—H28'	0.9500
C15—C19	1.531 (2)	C27'—H27C	0.9500
C16—C17	1.395 (2)	C27'—H27D	0.9500

O1—C1—C2	123.87 (19)	C18—C17—C16	119.59 (14)
O1—C1—H1	118.1	C18—C17—C23	120.72 (15)
C2—C1—H1	118.1	C16—C17—C23	119.67 (14)
C3—C2—C7	119.57 (15)	O3—C18—C17	119.40 (13)
C3—C2—C1	120.97 (16)	O3—C18—C13	120.08 (13)
C7—C2—C1	119.45 (16)	C17—C18—C13	120.35 (14)
C2—C3—O2	119.90 (14)	C22—C19—C15	108.93 (13)
C2—C3—C4	120.58 (15)	C22—C19—C21	109.61 (15)
O2—C3—C4	119.40 (14)	C15—C19—C21	109.38 (14)
C5—C4—C3	118.05 (14)	C22—C19—C20	108.97 (15)
C5—C4—C12	120.31 (14)	C15—C19—C20	112.11 (14)
C3—C4—C12	121.42 (14)	C21—C19—C20	107.81 (14)
C4—C5—C6	123.05 (14)	C19—C20—H20A	109.5
C4—C5—H5	118.5	C19—C20—H20B	109.5
C6—C5—H5	118.5	H20A—C20—H20B	109.5
C7—C6—C5	117.22 (15)	C19—C20—H20C	109.5
C7—C6—C8	123.49 (15)	H20A—C20—H20C	109.5
C5—C6—C8	119.29 (15)	H20B—C20—H20C	109.5
C6—C7—C2	121.42 (15)	C19—C21—H21A	109.5
C6—C7—H7	119.3	C19—C21—H21B	109.5
C2—C7—H7	119.3	H21A—C21—H21B	109.5
C6—C8—C9	112.13 (16)	C19—C21—H21C	109.5
C6—C8—C10	110.10 (15)	H21A—C21—H21C	109.5
C9—C8—C10	108.64 (15)	H21B—C21—H21C	109.5
C6—C8—C11	108.22 (14)	C19—C22—H22A	109.5
C9—C8—C11	109.38 (18)	C19—C22—H22B	109.5
C10—C8—C11	108.31 (18)	H22A—C22—H22B	109.5
C8—C9—H9A	109.5	C19—C22—H22C	109.5
C8—C9—H9B	109.5	H22A—C22—H22C	109.5
H9A—C9—H9B	109.5	H22B—C22—H22C	109.5
C8—C9—H9C	109.5	O4—C23—C17	123.79 (17)
H9A—C9—H9C	109.5	O4—C23—H23	118.1
H9B—C9—H9C	109.5	C17—C23—H23	118.1
C8—C10—H10A	109.5	C3—O2—C26	113.02 (12)
C8—C10—H10B	109.5	O2—C26—C25	111.32 (17)
H10A—C10—H10B	109.5	O2—C26—H26A	109.4
C8—C10—H10C	109.5	C25—C26—H26A	109.4
H10A—C10—H10C	109.5	O2—C26—H26B	109.4
H10B—C10—H10C	109.5	C25—C26—H26B	109.4
C8—C11—H11A	109.5	H26A—C26—H26B	108.0
C8—C11—H11B	109.5	C24—C25—C26	125.9 (2)
H11A—C11—H11B	109.5	C24—C25—H25	117.1
C8—C11—H11C	109.5	C26—C25—H25	117.1
H11A—C11—H11C	109.5	C25—C24—H24A	120.0
H11B—C11—H11C	109.5	C25—C24—H24B	120.0
C4—C12—C13	115.99 (13)	H24A—C24—H24B	120.0
C4—C12—H12A	108.3	C18—O3—C29	116.08 (12)
C13—C12—H12A	108.3	O3—C29—C28	107.39 (19)
C4—C12—H12B	108.3	O3—C29—H29A	110.2
C13—C12—H12B	108.3	C28—C29—H29A	110.2
H12A—C12—H12B	107.4	O3—C29—H29B	110.2
C14—C13—C18	118.18 (14)	C28—C29—H29B	110.2
C14—C13—C12	122.38 (13)	H29A—C29—H29B	108.5
C18—C13—C12	119.44 (13)	C27—C28—C29	127.5 (6)
C13—C14—C15	122.99 (14)	C27—C28—H28	116.3
C13—C14—H14	118.5	C29—C28—H28	116.3
C15—C14—H14	118.5	C28—C27—H27A	120.0
C16—C15—C14	117.04 (14)	C28—C27—H27B	120.0
C16—C15—C19	123.37 (14)	H27A—C27—H27B	120.0
C14—C15—C19	119.59 (13)	C27'—C28'—H28'	121.3
C15—C16—C17	121.81 (14)	C28'—C27'—H27C	120.0
C15—C16—H16	119.1	C28'—C27'—H27D	120.0
C17—C16—H16	119.1	H27C—C27'—H27D	120.0

O1—C1—C2—C3	170.72 (16)	C13—C14—C15—C16	−1.0 (2)
O1—C1—C2—C7	−9.0 (3)	C13—C14—C15—C19	179.52 (14)
C7—C2—C3—O2	178.41 (13)	C14—C15—C16—C17	−0.7 (2)
C1—C2—C3—O2	−1.3 (2)	C19—C15—C16—C17	178.78 (14)
C7—C2—C3—C4	2.3 (2)	C15—C16—C17—C18	1.6 (2)
C1—C2—C3—C4	−177.39 (14)	C15—C16—C17—C23	−177.01 (14)
C2—C3—C4—C5	−3.3 (2)	C16—C17—C18—O3	−176.18 (13)
O2—C3—C4—C5	−179.43 (13)	C23—C17—C18—O3	2.4 (2)
C2—C3—C4—C12	171.27 (14)	C16—C17—C18—C13	−0.8 (2)
O2—C3—C4—C12	−4.8 (2)	C23—C17—C18—C13	177.74 (14)
C3—C4—C5—C6	1.5 (2)	C14—C13—C18—O3	174.56 (13)
C12—C4—C5—C6	−173.22 (14)	C12—C13—C18—O3	−5.5 (2)
C4—C5—C6—C7	1.4 (2)	C14—C13—C18—C17	−0.7 (2)
C4—C5—C6—C8	−178.22 (14)	C12—C13—C18—C17	179.24 (14)
C5—C6—C7—C2	−2.5 (2)	C16—C15—C19—C22	−116.42 (17)
C8—C6—C7—C2	177.14 (14)	C14—C15—C19—C22	63.02 (19)
C3—C2—C7—C6	0.7 (2)	C16—C15—C19—C21	123.80 (16)
C1—C2—C7—C6	−179.59 (15)	C14—C15—C19—C21	−56.76 (19)
C7—C6—C8—C9	3.7 (2)	C16—C15—C19—C20	4.3 (2)
C5—C6—C8—C9	−176.71 (15)	C14—C15—C19—C20	−176.29 (15)
C7—C6—C8—C10	124.76 (18)	C18—C17—C23—O4	−175.62 (16)
C5—C6—C8—C10	−55.6 (2)	C16—C17—C23—O4	3.0 (3)
C7—C6—C8—C11	−117.05 (19)	C2—C3—O2—C26	100.36 (18)
C5—C6—C8—C11	62.6 (2)	C4—C3—O2—C26	−83.54 (18)
C5—C4—C12—C13	−56.86 (19)	C3—O2—C26—C25	161.55 (16)
C3—C4—C12—C13	128.65 (15)	O2—C26—C25—C24	−10.7 (3)
C4—C12—C13—C14	−29.0 (2)	C17—C18—O3—C29	−101.49 (17)
C4—C12—C13—C18	150.97 (14)	C13—C18—O3—C29	83.16 (18)
C18—C13—C14—C15	1.7 (2)	C18—O3—C29—C28	−149.5 (2)
C12—C13—C14—C15	−178.28 (14)	O3—C29—C28—C27	−105.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.46	3.406 (2)	171
C14—H14···O4ⁱⁱ	0.95	2.62	3.560 (2)	170

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

(IVa) 5,5'-di-tert-butyl-2,2'-dihydroxy-3,3'-methanediyldibenzaldehyde top

Crystal data top

C₂₃H₂₈O₄	D_x = 1.238 Mg m⁻³
M_r = 368.45	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3205 reflections
a = 12.7930 (7) Å	θ = 2.8–22.8°
c = 24.158 (2) Å	µ = 0.08 mm⁻¹
V = 3953.7 (4) Å³	T = 150 K
Z = 8	Block ## AUTHOR: Tablet?, yellow
F(000) = 1584	0.28 × 0.20 × 0.05 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1736 independent reflections
Radiation source: normal-focus sealed tube	1203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→15
T_min = 0.931, T_max = 1.000	k = −15→15
19093 measured reflections	l = −28→28

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0446P)² + 4.6694P] where P = (F_o² + 2F_c²)/3
1736 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₈O₄	Z = 8
M_r = 368.45	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.08 mm⁻¹
a = 12.7930 (7) Å	T = 150 K
c = 24.158 (2) Å	0.28 × 0.20 × 0.05 mm
V = 3953.7 (4) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1736 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1203 reflections with I > 2σ(I)
T_min = 0.931, T_max = 1.000	R_int = 0.056
19093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
1736 reflections	Δρ_min = −0.21 e Å⁻³
125 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.91517 (13)	0.36217 (12)	0.07535 (7)	0.0529 (5)
C1	1.00238 (18)	0.38549 (17)	0.05825 (10)	0.0448 (6)
H1	1.0406	0.3332	0.0390	0.054*
C2	1.05164 (16)	0.48672 (16)	0.06515 (9)	0.0359 (5)
C3	0.99989 (15)	0.56794 (16)	0.09323 (9)	0.0359 (5)
O2	0.90144 (11)	0.55533 (13)	0.11373 (7)	0.0472 (4)
H2	0.8850 (17)	0.4864 (18)	0.1065 (9)	0.040*
C4	1.05026 (15)	0.66379 (15)	0.10117 (8)	0.0332 (5)
C5	1.14976 (15)	0.67573 (16)	0.07960 (8)	0.0342 (5)
H5	1.1840	0.7408	0.0851	0.041*
C6	1.20321 (15)	0.59785 (15)	0.05009 (8)	0.0332 (5)
C7	1.15190 (16)	0.50302 (16)	0.04417 (9)	0.0364 (5)
H7	1.1860	0.4476	0.0253	0.044*
C8	1.31390 (16)	0.61729 (16)	0.02875 (9)	0.0379 (5)
C9	1.3448 (2)	0.5401 (2)	−0.01681 (11)	0.0575 (7)
H9A	1.4161	0.5554	−0.0293	0.086*
H9B	1.2964	0.5469	−0.0481	0.086*
H9C	1.3418	0.4687	−0.0022	0.086*
C10	1.39030 (18)	0.6054 (2)	0.07729 (11)	0.0560 (7)
H10A	1.3713	0.6544	0.1068	0.084*
H10B	1.4615	0.6204	0.0646	0.084*
H10C	1.3870	0.5337	0.0915	0.084*
C11	1.3234 (2)	0.72779 (19)	0.00507 (9)	0.0584 (7)
H11A	1.3039	0.7788	0.0335	0.088*
H11B	1.2768	0.7350	−0.0269	0.088*
H11C	1.3958	0.7403	−0.0066	0.088*
C12	1.0000	0.75000	0.13460 (9)	0.0367 (7)
H12A	0.9461	0.7186	0.1589	0.044*	0.50
H12B	1.0539	0.7814	0.1589	0.044*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0454 (10)	0.0437 (10)	0.0695 (12)	−0.0126 (7)	−0.0040 (8)	0.0090 (8)
C1	0.0448 (14)	0.0360 (13)	0.0535 (14)	−0.0042 (10)	−0.0042 (11)	0.0074 (10)
C2	0.0349 (11)	0.0302 (11)	0.0425 (12)	−0.0024 (9)	−0.0028 (9)	0.0062 (9)
C3	0.0276 (11)	0.0394 (12)	0.0408 (12)	0.0022 (9)	−0.0014 (9)	0.0069 (9)
O2	0.0334 (9)	0.0452 (10)	0.0629 (11)	−0.0046 (7)	0.0061 (7)	0.0008 (8)
C4	0.0335 (11)	0.0312 (11)	0.0350 (11)	0.0047 (9)	−0.0025 (9)	0.0020 (9)
C5	0.0345 (11)	0.0293 (11)	0.0390 (12)	0.0003 (9)	−0.0015 (9)	0.0029 (9)
C6	0.0303 (11)	0.0304 (11)	0.0388 (12)	0.0016 (8)	−0.0005 (9)	0.0038 (9)
C7	0.0378 (12)	0.0285 (11)	0.0428 (12)	0.0042 (9)	−0.0001 (9)	0.0014 (9)
C8	0.0330 (11)	0.0328 (11)	0.0478 (12)	0.0013 (9)	0.0046 (10)	−0.0002 (10)
C9	0.0472 (14)	0.0562 (16)	0.0691 (18)	−0.0016 (12)	0.0199 (13)	−0.0177 (13)
C10	0.0350 (13)	0.0681 (17)	0.0649 (17)	−0.0004 (12)	−0.0030 (12)	0.0025 (14)
C11	0.0546 (16)	0.0455 (14)	0.0750 (18)	−0.0014 (11)	0.0242 (14)	0.0121 (13)
C12	0.0348 (16)	0.0377 (17)	0.0377 (16)	0.0049 (13)	0.000	0.000

Geometric parameters (Å, º) top

O1—C1	1.227 (3)	C8—C9	1.530 (3)
C1—C2	1.450 (3)	C8—C11	1.530 (3)
C1—H1	0.9500	C8—C10	1.534 (3)
C2—C7	1.395 (3)	C9—H9A	0.9800
C2—C3	1.406 (3)	C9—H9B	0.9800
C3—O2	1.363 (2)	C9—H9C	0.9800
C3—C4	1.399 (3)	C10—H10A	0.9800
O2—H2	0.92 (2)	C10—H10B	0.9800
C4—C5	1.384 (3)	C10—H10C	0.9800
C4—C12	1.511 (3)	C11—H11A	0.9800
C5—C6	1.403 (3)	C11—H11B	0.9800
C5—H5	0.9500	C11—H11C	0.9800
C6—C7	1.387 (3)	C12—C4ⁱ	1.510 (3)
C6—C8	1.527 (3)	C12—H12A	0.9900
C7—H7	0.9500	C12—H12B	0.9900

O1—C1—C2	125.0 (2)	C9—C8—C10	108.7 (2)
O1—C1—H1	117.5	C11—C8—C10	109.05 (19)
C2—C1—H1	117.5	C8—C9—H9A	109.5
C7—C2—C3	119.83 (19)	C8—C9—H9B	109.5
C7—C2—C1	119.4 (2)	H9A—C9—H9B	109.5
C3—C2—C1	120.7 (2)	C8—C9—H9C	109.5
O2—C3—C4	118.67 (19)	H9A—C9—H9C	109.5
O2—C3—C2	121.52 (19)	H9B—C9—H9C	109.5
C4—C3—C2	119.81 (18)	C8—C10—H10A	109.5
C3—O2—H2	104.7 (14)	C8—C10—H10B	109.5
C5—C4—C3	117.98 (19)	H10A—C10—H10B	109.5
C5—C4—C12	120.80 (19)	C8—C10—H10C	109.5
C3—C4—C12	121.16 (19)	H10A—C10—H10C	109.5
C4—C5—C6	124.13 (19)	H10B—C10—H10C	109.5
C4—C5—H5	117.9	C8—C11—H11A	109.5
C6—C5—H5	117.9	C8—C11—H11B	109.5
C7—C6—C5	116.30 (19)	H11A—C11—H11B	109.5
C7—C6—C8	123.13 (18)	C8—C11—H11C	109.5
C5—C6—C8	120.51 (18)	H11A—C11—H11C	109.5
C6—C7—C2	121.9 (2)	H11B—C11—H11C	109.5
C6—C7—H7	119.0	C4ⁱ—C12—C4	115.4 (2)
C2—C7—H7	119.0	C4ⁱ—C12—H12A	108.4
C6—C8—C9	112.16 (18)	C4—C12—H12A	108.4
C6—C8—C11	110.52 (17)	C4ⁱ—C12—H12B	108.4
C9—C8—C11	107.88 (19)	C4—C12—H12B	108.4
C6—C8—C10	108.48 (19)	H12A—C12—H12B	107.5

O1—C1—C2—C7	179.3 (2)	C4—C5—C6—C8	−178.80 (19)
O1—C1—C2—C3	0.1 (4)	C5—C6—C7—C2	1.6 (3)
C7—C2—C3—O2	179.23 (19)	C8—C6—C7—C2	178.56 (19)
C1—C2—C3—O2	−1.5 (3)	C3—C2—C7—C6	0.0 (3)
C7—C2—C3—C4	−1.6 (3)	C1—C2—C7—C6	−179.3 (2)
C1—C2—C3—C4	177.7 (2)	C7—C6—C8—C9	21.4 (3)
O2—C3—C4—C5	−179.34 (18)	C5—C6—C8—C9	−161.8 (2)
C2—C3—C4—C5	1.4 (3)	C7—C6—C8—C11	141.8 (2)
O2—C3—C4—C12	3.6 (3)	C5—C6—C8—C11	−41.4 (3)
C2—C3—C4—C12	−175.65 (19)	C7—C6—C8—C10	−98.7 (2)
C3—C4—C5—C6	0.2 (3)	C5—C6—C8—C10	78.1 (2)
C12—C4—C5—C6	177.35 (19)	C5—C4—C12—C4ⁱ	81.9 (2)
C4—C5—C6—C7	−1.7 (3)	C3—C4—C12—C4ⁱ	−101.1 (2)

Symmetry code: (i) −x+2, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.92 (2)	1.80 (2)	2.645 (2)	151 (2)

(IVb) 2,2'–Dihydroxy–5,5'–di–tert–butyl–3,3'– methanediyldibenzaldehyde top

Crystal data top

C₂₃H₂₈O₄	F(000) = 1584
M_r = 368.45	D_x = 1.174 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.809 (2) Å	Cell parameters from 3051 reflections
b = 8.4543 (7) Å	θ = 2.6–25.6°
c = 21.3720 (18) Å	µ = 0.08 mm⁻¹
β = 120.618 (1)°	T = 153 K
V = 4168.7 (6) Å³	Tablet, light brown
Z = 8	0.48 × 0.38 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3668 independent reflections
Radiation source: normal-focus sealed tube	2235 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −31→31
T_min = 0.919, T_max = 1.000	k = −10→10
14739 measured reflections	l = −25→25

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0393P)² + 4.8718P] where P = (F_o² + 2F_c²)/3
3668 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₈O₄	V = 4168.7 (6) Å³
M_r = 368.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.809 (2) Å	µ = 0.08 mm⁻¹
b = 8.4543 (7) Å	T = 153 K
c = 21.3720 (18) Å	0.48 × 0.38 × 0.16 mm
β = 120.618 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3668 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2235 reflections with I > 2σ(I)
T_min = 0.919, T_max = 1.000	R_int = 0.049
14739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.20 e Å⁻³
3668 reflections	Δρ_min = −0.18 e Å⁻³
251 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.12612 (7)	0.3427 (2)	0.17034 (10)	0.0614 (5)
C1	0.07491 (11)	0.3578 (3)	0.12349 (14)	0.0472 (6)
H1	0.0660	0.4217	0.0825	0.057*
C2	0.02703 (9)	0.2858 (3)	0.12591 (12)	0.0347 (5)
C3	0.03676 (9)	0.1916 (3)	0.18513 (12)	0.0352 (5)
C4	−0.00989 (10)	0.1207 (3)	0.18602 (12)	0.0338 (5)
C5	−0.06496 (10)	0.1474 (3)	0.12771 (12)	0.0356 (6)
H5	−0.0966	0.0972	0.1278	0.043*
C6	−0.07678 (9)	0.2444 (3)	0.06828 (12)	0.0350 (5)
C7	−0.02974 (9)	0.3110 (3)	0.06866 (12)	0.0367 (6)
H7	−0.0360	0.3757	0.0290	0.044*
O2	0.09102 (7)	0.1694 (2)	0.24251 (9)	0.0448 (4)
H2	0.1181 (10)	0.220 (3)	0.2342 (13)	0.050*
C8	−0.13972 (10)	0.2741 (3)	0.00882 (13)	0.0424 (6)
C9	−0.14402 (11)	0.3823 (3)	−0.05135 (13)	0.0528 (7)
H9A	−0.1253	0.4838	−0.0302	0.079*
H9B	−0.1849	0.4002	−0.0877	0.079*
H9C	−0.1246	0.3321	−0.0746	0.079*
C10	−0.16911 (11)	0.1174 (3)	−0.02543 (15)	0.0604 (8)
H10A	−0.2094	0.1371	−0.0635	0.091*
H10B	−0.1684	0.0486	0.0119	0.091*
H10C	−0.1485	0.0659	−0.0468	0.091*
C11	−0.17152 (10)	0.3556 (3)	0.04259 (14)	0.0526 (7)
H11A	−0.1524	0.4562	0.0645	0.079*
H11B	−0.1707	0.2872	0.0801	0.079*
H11C	−0.2118	0.3757	0.0048	0.079*
C12	0.0000	0.0212 (4)	0.2500	0.0396 (8)
H12A	−0.0341	−0.0477	0.2350	0.048*	0.50
H12B	0.0341	−0.0477	0.2650	0.048*	0.50
O3	0.04622 (7)	0.8544 (2)	0.48082 (9)	0.0523 (5)
C13	−0.00570 (11)	0.8664 (3)	0.43552 (13)	0.0432 (6)
H13	−0.0284	0.9321	0.4475	0.052*
C14	−0.03482 (9)	0.7891 (3)	0.36593 (12)	0.0342 (5)
C15	−0.00390 (9)	0.6939 (3)	0.34339 (12)	0.0326 (5)
C16	−0.03278 (9)	0.6202 (2)	0.27591 (12)	0.0315 (5)
C17	−0.09193 (9)	0.6446 (3)	0.23255 (12)	0.0342 (5)
H17	−0.1117	0.5928	0.1868	0.041*
C18	−0.12444 (9)	0.7414 (3)	0.25209 (12)	0.0348 (5)
C19	−0.09454 (9)	0.8120 (3)	0.31941 (12)	0.0358 (5)
H19	−0.1149	0.8782	0.3348	0.043*
O4	0.05409 (7)	0.6738 (2)	0.38596 (9)	0.0417 (4)
H4	0.0659 (10)	0.725 (3)	0.4270 (13)	0.050*
C20	−0.18896 (10)	0.7661 (3)	0.19921 (13)	0.0430 (6)
C21	−0.19675 (12)	0.8506 (4)	0.13167 (15)	0.0688 (9)
H21A	−0.1772	0.9535	0.1456	0.103*
H21B	−0.2382	0.8663	0.0971	0.103*
H21C	−0.1799	0.7863	0.1090	0.103*
C22	−0.21941 (11)	0.6067 (4)	0.17775 (18)	0.0700 (9)
H22A	−0.2609	0.6227	0.1437	0.105*
H22B	−0.2140	0.5522	0.2213	0.105*
H22C	−0.2030	0.5424	0.1545	0.105*
C23	−0.21703 (11)	0.8669 (4)	0.23221 (16)	0.0645 (8)
H23A	−0.1979	0.9703	0.2461	0.097*
H23B	−0.2130	0.8137	0.2753	0.097*
H23C	−0.2582	0.8814	0.1964	0.097*
C24	0.0000	0.5208 (4)	0.2500	0.0362 (8)
H24A	0.0277	0.4518	0.2902	0.043*	0.50
H24B	−0.0277	0.4518	0.2098	0.043*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0376 (11)	0.0847 (15)	0.0625 (12)	−0.0085 (10)	0.0259 (10)	−0.0015 (11)
C1	0.0446 (16)	0.0551 (17)	0.0491 (15)	−0.0064 (13)	0.0290 (14)	−0.0014 (13)
C2	0.0363 (13)	0.0363 (13)	0.0377 (13)	−0.0013 (10)	0.0234 (11)	−0.0038 (10)
C3	0.0356 (13)	0.0336 (13)	0.0373 (13)	0.0014 (10)	0.0193 (11)	−0.0060 (11)
C4	0.0412 (14)	0.0278 (12)	0.0365 (13)	−0.0002 (10)	0.0227 (11)	−0.0057 (10)
C5	0.0376 (13)	0.0333 (13)	0.0411 (14)	−0.0068 (10)	0.0238 (12)	−0.0078 (11)
C6	0.0371 (13)	0.0377 (13)	0.0334 (13)	−0.0020 (10)	0.0202 (11)	−0.0052 (10)
C7	0.0405 (14)	0.0394 (14)	0.0353 (13)	0.0013 (11)	0.0230 (12)	−0.0003 (11)
O2	0.0366 (10)	0.0507 (11)	0.0447 (10)	0.0028 (8)	0.0189 (8)	0.0008 (8)
C8	0.0352 (13)	0.0547 (16)	0.0392 (14)	−0.0014 (12)	0.0203 (11)	−0.0043 (12)
C9	0.0445 (15)	0.072 (2)	0.0403 (15)	0.0080 (14)	0.0204 (12)	0.0077 (14)
C10	0.0465 (16)	0.068 (2)	0.0548 (17)	−0.0080 (14)	0.0174 (14)	−0.0129 (15)
C11	0.0404 (15)	0.0721 (19)	0.0497 (16)	0.0072 (13)	0.0262 (13)	0.0012 (14)
C12	0.049 (2)	0.0293 (18)	0.042 (2)	0.000	0.0250 (17)	0.000
O3	0.0485 (11)	0.0675 (13)	0.0395 (10)	−0.0082 (9)	0.0214 (9)	−0.0079 (9)
C13	0.0490 (16)	0.0464 (15)	0.0411 (14)	−0.0042 (12)	0.0280 (13)	−0.0036 (12)
C14	0.0397 (13)	0.0352 (13)	0.0329 (12)	−0.0042 (10)	0.0223 (11)	0.0003 (10)
C15	0.0332 (13)	0.0332 (13)	0.0363 (13)	−0.0021 (10)	0.0214 (11)	0.0048 (10)
C16	0.0379 (13)	0.0267 (12)	0.0373 (13)	−0.0019 (10)	0.0246 (11)	0.0015 (10)
C17	0.0386 (13)	0.0309 (13)	0.0389 (13)	−0.0076 (10)	0.0239 (11)	−0.0026 (10)
C18	0.0345 (13)	0.0361 (13)	0.0393 (13)	−0.0040 (10)	0.0228 (11)	−0.0004 (11)
C19	0.0398 (13)	0.0332 (13)	0.0429 (14)	−0.0011 (10)	0.0273 (12)	−0.0003 (11)
O4	0.0357 (9)	0.0492 (11)	0.0382 (9)	0.0016 (8)	0.0175 (8)	0.0007 (8)
C20	0.0340 (13)	0.0520 (16)	0.0455 (14)	−0.0022 (11)	0.0221 (12)	−0.0032 (12)
C21	0.0496 (17)	0.097 (2)	0.0554 (18)	0.0130 (16)	0.0237 (15)	0.0161 (17)
C22	0.0390 (16)	0.071 (2)	0.093 (2)	−0.0143 (15)	0.0291 (16)	−0.0139 (18)
C23	0.0382 (15)	0.085 (2)	0.070 (2)	0.0089 (15)	0.0274 (14)	−0.0112 (17)
C24	0.0411 (19)	0.0281 (17)	0.046 (2)	0.000	0.0270 (16)	0.000

Geometric parameters (Å, º) top

O1—C1	1.226 (3)	O3—C13	1.230 (3)
C1—C2	1.445 (3)	C13—C14	1.437 (3)
C1—H1	0.9500	C13—H13	0.9500
C2—C7	1.401 (3)	C14—C19	1.403 (3)
C2—C3	1.403 (3)	C14—C15	1.405 (3)
C3—O2	1.356 (3)	C15—O4	1.354 (3)
C3—C4	1.396 (3)	C15—C16	1.389 (3)
C4—C5	1.382 (3)	C16—C17	1.385 (3)
C4—C12	1.509 (3)	C16—C24	1.510 (3)
C5—C6	1.406 (3)	C17—C18	1.405 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.377 (3)	C18—C19	1.377 (3)
C6—C8	1.530 (3)	C18—C20	1.524 (3)
C7—H7	0.9500	C19—H19	0.9500
O2—H2	0.94 (2)	O4—H4	0.88 (2)
C8—C10	1.524 (4)	C20—C22	1.520 (4)
C8—C11	1.533 (3)	C20—C23	1.527 (3)
C8—C9	1.534 (3)	C20—C21	1.526 (4)
C9—H9A	0.9800	C21—H21A	0.9800
C9—H9B	0.9800	C21—H21B	0.9800
C9—H9C	0.9800	C21—H21C	0.9800
C10—H10A	0.9800	C22—H22A	0.9800
C10—H10B	0.9800	C22—H22B	0.9800
C10—H10C	0.9800	C22—H22C	0.9800
C11—H11A	0.9800	C23—H23A	0.9800
C11—H11B	0.9800	C23—H23B	0.9800
C11—H11C	0.9800	C23—H23C	0.9800
C12—C4ⁱ	1.509 (3)	C24—C16ⁱ	1.510 (3)
C12—H12A	0.9900	C24—H24A	0.9900
C12—H12B	0.9900	C24—H24B	0.9900

O1—C1—C2	124.9 (2)	O3—C13—C14	125.3 (2)
O1—C1—H1	117.5	O3—C13—H13	117.4
C2—C1—H1	117.5	C14—C13—H13	117.4
C7—C2—C3	119.6 (2)	C19—C14—C15	119.7 (2)
C7—C2—C1	119.6 (2)	C19—C14—C13	119.5 (2)
C3—C2—C1	120.7 (2)	C15—C14—C13	120.7 (2)
O2—C3—C4	119.0 (2)	O4—C15—C16	118.93 (19)
O2—C3—C2	121.0 (2)	O4—C15—C14	121.2 (2)
C4—C3—C2	120.0 (2)	C16—C15—C14	119.9 (2)
C5—C4—C3	118.1 (2)	C17—C16—C15	118.1 (2)
C5—C4—C12	121.46 (18)	C17—C16—C24	121.28 (18)
C3—C4—C12	120.42 (18)	C15—C16—C24	120.63 (18)
C4—C5—C6	123.8 (2)	C16—C17—C18	124.1 (2)
C4—C5—H5	118.1	C16—C17—H17	118.0
C6—C5—H5	118.1	C18—C17—H17	118.0
C7—C6—C5	116.6 (2)	C19—C18—C17	116.4 (2)
C7—C6—C8	123.9 (2)	C19—C18—C20	123.5 (2)
C5—C6—C8	119.5 (2)	C17—C18—C20	120.1 (2)
C6—C7—C2	121.8 (2)	C18—C19—C14	121.8 (2)
C6—C7—H7	119.1	C18—C19—H19	119.1
C2—C7—H7	119.1	C14—C19—H19	119.1
C3—O2—H2	110.1 (15)	C15—O4—H4	108.5 (16)
C10—C8—C6	109.8 (2)	C22—C20—C18	109.5 (2)
C10—C8—C11	110.0 (2)	C22—C20—C23	108.6 (2)
C6—C8—C11	108.98 (19)	C18—C20—C23	112.0 (2)
C10—C8—C9	108.4 (2)	C22—C20—C21	109.6 (2)
C6—C8—C9	111.98 (19)	C18—C20—C21	108.81 (19)
C11—C8—C9	107.7 (2)	C23—C20—C21	108.3 (2)
C8—C9—H9A	109.5	C20—C21—H21A	109.5
C8—C9—H9B	109.5	C20—C21—H21B	109.5
H9A—C9—H9B	109.5	H21A—C21—H21B	109.5
C8—C9—H9C	109.5	C20—C21—H21C	109.5
H9A—C9—H9C	109.5	H21A—C21—H21C	109.5
H9B—C9—H9C	109.5	H21B—C21—H21C	109.5
C8—C10—H10A	109.5	C20—C22—H22A	109.5
C8—C10—H10B	109.5	C20—C22—H22B	109.5
H10A—C10—H10B	109.5	H22A—C22—H22B	109.5
C8—C10—H10C	109.5	C20—C22—H22C	109.5
H10A—C10—H10C	109.5	H22A—C22—H22C	109.5
H10B—C10—H10C	109.5	H22B—C22—H22C	109.5
C8—C11—H11A	109.5	C20—C23—H23A	109.5
C8—C11—H11B	109.5	C20—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C8—C11—H11C	109.5	C20—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C4ⁱ—C12—C4	112.3 (3)	C16ⁱ—C24—C16	112.4 (2)
C4ⁱ—C12—H12A	109.2	C16ⁱ—C24—H24A	109.1
C4—C12—H12A	109.2	C16—C24—H24A	109.1
C4ⁱ—C12—H12B	109.2	C16ⁱ—C24—H24B	109.1
C4—C12—H12B	109.2	C16—C24—H24B	109.1
H12A—C12—H12B	107.9	H24A—C24—H24B	107.9

O1—C1—C2—C7	−179.5 (2)	O3—C13—C14—C19	179.5 (2)
O1—C1—C2—C3	0.8 (4)	O3—C13—C14—C15	−2.0 (4)
C7—C2—C3—O2	−177.7 (2)	C19—C14—C15—O4	177.66 (19)
C1—C2—C3—O2	2.0 (3)	C13—C14—C15—O4	−0.8 (3)
C7—C2—C3—C4	1.4 (3)	C19—C14—C15—C16	−1.4 (3)
C1—C2—C3—C4	−178.9 (2)	C13—C14—C15—C16	−179.9 (2)
O2—C3—C4—C5	178.70 (19)	O4—C15—C16—C17	−178.75 (19)
C2—C3—C4—C5	−0.4 (3)	C14—C15—C16—C17	0.4 (3)
O2—C3—C4—C12	0.1 (3)	O4—C15—C16—C24	−0.7 (3)
C2—C3—C4—C12	−179.0 (2)	C14—C15—C16—C24	178.5 (2)
C3—C4—C5—C6	−1.4 (3)	C15—C16—C17—C18	1.0 (3)
C12—C4—C5—C6	177.2 (2)	C24—C16—C17—C18	−177.0 (2)
C4—C5—C6—C7	2.1 (3)	C16—C17—C18—C19	−1.3 (3)
C4—C5—C6—C8	−176.2 (2)	C16—C17—C18—C20	177.5 (2)
C5—C6—C7—C2	−1.1 (3)	C17—C18—C19—C14	0.1 (3)
C8—C6—C7—C2	177.2 (2)	C20—C18—C19—C14	−178.6 (2)
C3—C2—C7—C6	−0.6 (3)	C15—C14—C19—C18	1.2 (3)
C1—C2—C7—C6	179.7 (2)	C13—C14—C19—C18	179.7 (2)
C7—C6—C8—C10	122.3 (2)	C19—C18—C20—C22	−125.2 (3)
C5—C6—C8—C10	−59.5 (3)	C17—C18—C20—C22	56.1 (3)
C7—C6—C8—C11	−117.2 (2)	C19—C18—C20—C23	−4.6 (3)
C5—C6—C8—C11	61.0 (3)	C17—C18—C20—C23	176.7 (2)
C7—C6—C8—C9	1.8 (3)	C19—C18—C20—C21	115.0 (3)
C5—C6—C8—C9	−180.0 (2)	C17—C18—C20—C21	−63.7 (3)
C5—C4—C12—C4ⁱ	−100.4 (2)	C17—C16—C24—C16ⁱ	101.4 (2)
C3—C4—C12—C4ⁱ	78.14 (18)	C15—C16—C24—C16ⁱ	−76.67 (18)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.94 (2)	1.81 (2)	2.625 (3)	144 (2)
O4—H4···O3	0.88 (2)	1.85 (2)	2.631 (2)	147 (2)
C13—H13···O3ⁱⁱ	0.95	2.57	3.454 (3)	156

Symmetry code: (ii) −x, −y+2, −z+1.

Experimental details

	(II)	(III)	(IVa)	(IVb)
Crystal data
Chemical formula	C₂₉H₄₀O₄	C₂₉H₃₆O₄	C₂₃H₂₈O₄	C₂₃H₂₈O₄
M_r	452.61	448.58	368.45	368.45
Crystal system, space group	Triclinic, P1	Monoclinic, P2₁/c	Tetragonal, I4₁/a	Monoclinic, C2/c
Temperature (K)	150	150	150	153
a, b, c (Å)	10.6025 (11), 11.9199 (12), 12.4180 (13)	16.2931 (10), 10.1951 (6), 16.4318 (10)	12.7930 (7), 12.7930 (7), 24.158 (2)	26.809 (2), 8.4543 (7), 21.3720 (18)
α, β, γ (°)	64.611 (2), 82.672 (2), 66.330 (2)	90, 108.367 (1), 90	90, 90, 90	90, 120.618 (1), 90
V (Å³)	1296.7 (2)	2590.4 (3)	3953.7 (4)	4168.7 (6)
Z	2	4	8	8
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.08	0.08	0.08	0.08
Crystal size (mm)	0.29 × 0.17 × 0.12	0.26 × 0.16 × 0.14	0.28 × 0.20 × 0.05	0.48 × 0.38 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer	Bruker SMART 1000 CCD area-detector diffractometer	Bruker SMART 1000 CCD area-detector diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)	Multi-scan (SADABS; Sheldrick, 2001)	Multi-scan (SADABS; Sheldrick, 2001)	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.938, 1.000	0.900, 1.000	0.931, 1.000	0.919, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9408, 4565, 3085	17928, 4559, 3620	19093, 1736, 1203	14739, 3668, 2235
R_int	0.025	0.020	0.056	0.049
(sin θ/λ)_max (Å⁻¹)	0.595	0.595	0.594	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.173, 1.04	0.043, 0.123, 1.02	0.043, 0.120, 1.04	0.047, 0.132, 1.01
No. of reflections	4565	4559	1736	3668
No. of parameters	310	317	125	251
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.22	0.29, −0.18	0.19, −0.21	0.20, −0.18

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2001), SHELXTL.

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OB···O4ⁱ	0.82	1.99	2.749 (2)	155
O1—H1OA···O4ⁱⁱ	0.83	1.93	2.744 (3)	166
O4—H4OA···O1ⁱ	0.91	1.85	2.749 (2)	167
O4—H4OB···O1ⁱⁱⁱ	0.84	1.90	2.744 (3)	177

Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) x−1, y, z.

Hydrogen-bond geometry (Å, º) for (III) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.46	3.406 (2)	171
C14—H14···O4ⁱⁱ	0.95	2.62	3.560 (2)	170

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) for (IVa) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.92 (2)	1.80 (2)	2.645 (2)	151 (2)

Hydrogen-bond geometry (Å, º) for (IVb) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.94 (2)	1.81 (2)	2.625 (3)	144 (2)
O4—H4···O3	0.88 (2)	1.85 (2)	2.631 (2)	147 (2)
C13—H13···O3ⁱ	0.95	2.57	3.454 (3)	156

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors thank Professor M. A. McKervey and Dr H. Q. N. Gunaratne, CSS Limited, for helpful discussions.

References

Barreira Fontecha, J., Goetz, S. & McKee, V. (2002). Angew. Chem. Int. Ed. 41, 4554–4556. CrossRef Google Scholar
Boss, R. & Scheffold, R. (1976). Angew. Chem. 88, 578–579. CrossRef CAS Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dhawan, B. & Gutsche, C. D. (1983). J. Org. Chem. 48, 1536–1539. CrossRef CAS Web of Science Google Scholar
Masci, B., Levi Mortera, S., Seralessandri, L. & Thuery, P. (2004) Acta Cryst. C60, o107–o109. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SHELXTL (Version 6.12) and SADABS (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Taniguchi, S. (1984). Bull. Chem. Soc. Jpn, 57, 2683–2684. CrossRef CAS Web of Science Google Scholar

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ISSN: 2053-2296

Volume 60| Part 11| November 2004| Pages o776-o780

doi:10.1107/S010827010402089X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5,5′-Di-tert-butyl-2,2′-di­hy­droxy-3,3′-methanediyl­dibenz­aldehyde and its allyl-protected dialcohol and di­aldehyde precursors

Comment

Experimental

Compound (II)

Crystal data

Data collection

Refinement

Compound (III)

Crystal data

Data collection

Refinement

Polymorph (IVa)

Crystal data

Data collection

Refinement

Polymorph (IVb)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,5′-Di-tert-butyl-2,2′-dihydroxy-3,3′-methanediyldibenzaldehyde and its allyl-protected dialcohol and dialdehyde precursors