Crystal structure of (E)-4,4′-(but-2-ene-1,4-di­yl)bis­(2-meth­oxy­phenol)

Knight, K.S.; Carey, P.J.

doi:10.1107/S2056989015011585

organic compounds

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Crystal structure of (E)-4,4′-(but-2-ene-1,4-diyl)bis(2-methoxyphenol)

Kyle S. Knight ^a ^* and Patrick J. Carey ^a

^aDepartment of Chemistry, The University of Tennessee at Chattanooga, Chattanooga, TN 37403, USA
^*Correspondence e-mail: kyle-knight@utc.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 June 2015; accepted 15 June 2015; online 20 June 2015)

The title compound, C₁₈H₂₀O₄, was synthesized via the ruthenium-catalyzed alkene methathesis dimerization of eugenol. The whole molecule is generated by inversion symmetry; the center of inversion being located at the mid-point of the trans C=C bond. The phenol ring is inclined to the mean plane of the central C—C=C—C unit (r.m.s. deviation = 0.014 Å) by 68.83 (16)°. In the crystal, molecules are linked via O—H⋯O hydrogen bonds, involving the hydroxy and methoxy groups, forming undulating sheets parallel to (010).

Keywords: crystal structure; metathesis; dimerization of eugenol; hydrogen bonding.

CCDC reference: 1406832

1. Related literature

For a general review of alkene metathesis catalyzed by ruthenium carbenes, see: Grubbs (2004 ). For the second generation Grubbs ruthenium carbene catalyst, see: Scholl et al. (1999 ). For the synthesis of the title compound, see: Taber & Frankowski (2006 ).

2. Experimental

2.1. Crystal data

C₁₈H₂₀O₄
M_r = 300.34
Orthorhombic, P b c a
a = 4.8846 (2) Å
b = 10.7002 (4) Å
c = 29.5666 (11) Å
V = 1545.33 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 198 K
0.6 × 0.55 × 0.2 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.927, T_max = 1.000
25610 measured reflections
1352 independent reflections
1199 reflections with I > 2σ(I)
R_int = 0.036

2.3. Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.096
S = 1.05
1352 reflections
105 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O1ⁱ	0.78 (2)	2.57 (2)	3.1784 (13)	136 (1)
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1406832

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S2056989015011585/su5153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011585/su5153Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011585/su5153Isup3.cdx

Supporting information file. DOI: 10.1107/S2056989015011585/su5153Isup4.cml

checkCIF report

Synthesis and crystallization top

The title compound was prepared from eugenol by alkene metathesis dimerization using the second generation Grubbs ruthenium carbene catalyst (Scholl et al., 1999) as described previously (Taber & Frankowski, 2006).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydroxyl H atom was located in a difference Fourier map and refined with U_iso(H) = 1.2U_eq(O). The C-bound H atoms were positioned geometrically and constrained to ride on their parent atoms: C—H = 0.95 - 1.0 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq (C) for other H atoms.

Related literature top

For a general review of alkene metathesis catalyzed by ruthenium carbenes, see: Grubbs (2004). For the second generation Grubbs ruthenium carbene catalyst, see: Scholl et al. (1999). For the synthesis of the title compound, see: Taber & Frankowski (2006).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Unlabelled atoms are related to the labelled atoms by inversion symmetry (symmetry code: -x + 1, -y + 2, -z).
	Fig. 2. A view along the a axis of the crystal packing of the title compound, with hydrogen bonds shown as dashed lines (see Table 1 for details). C-bound H atoms have been omitted for clarity.

(E)-4,4'-(But-2-ene-1,4-diyl)bis(2-methoxyphenol) top

Crystal data top

C₁₈H₂₀O₄	D_x = 1.291 Mg m⁻³
M_r = 300.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9944 reflections
a = 4.8846 (2) Å	θ = 2.8–24.8°
b = 10.7002 (4) Å	µ = 0.09 mm⁻¹
c = 29.5666 (11) Å	T = 198 K
V = 1545.33 (10) Å³	Plate, colorless
Z = 4	0.6 × 0.55 × 0.2 mm
F(000) = 640

Data collection top

Bruker APEXII CCD diffractometer	1199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
T_min = 0.927, T_max = 1.000	k = −12→12
25610 measured reflections	l = −35→35
1352 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0476P)² + 0.352P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1352 reflections	Δρ_max = 0.16 e Å⁻³
105 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)

Crystal data top

C₁₈H₂₀O₄	V = 1545.33 (10) Å³
M_r = 300.34	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 4.8846 (2) Å	µ = 0.09 mm⁻¹
b = 10.7002 (4) Å	T = 198 K
c = 29.5666 (11) Å	0.6 × 0.55 × 0.2 mm

Data collection top

Bruker APEXII CCD diffractometer	1352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1199 reflections with I > 2σ(I)
T_min = 0.927, T_max = 1.000	R_int = 0.036
25610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
1352 reflections	Δρ_min = −0.13 e Å⁻³
105 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
O1	0.3753 (2)	0.94521 (9)	0.20535 (3)	0.0531 (3)
C1	0.1882 (3)	1.04703 (13)	0.20379 (5)	0.0505 (4)
H1A	0.2599	1.1120	0.1837	0.076*
H1B	0.1646	1.0815	0.2343	0.076*
H1C	0.0111	1.0178	0.1924	0.076*
C2	0.4437 (3)	0.88991 (11)	0.16499 (4)	0.0395 (3)
C3	0.3285 (3)	0.91684 (12)	0.12337 (4)	0.0454 (3)
H3	0.1922	0.9798	0.1211	0.054*
C4	0.4108 (3)	0.85237 (13)	0.08473 (4)	0.0475 (4)
C5	0.2924 (3)	0.88644 (16)	0.03888 (4)	0.0605 (4)
H5A	0.3136	0.8146	0.0181	0.073*
H5B	0.0941	0.9035	0.0422	0.073*
C6	0.4294 (3)	0.99880 (15)	0.01871 (4)	0.0554 (4)
H6	0.4116	1.0754	0.0347	0.066*
C7	0.6459 (3)	0.79875 (11)	0.16851 (4)	0.0419 (3)
O8	0.7636 (2)	0.77137 (10)	0.20946 (3)	0.0556 (3)
H8	0.699 (3)	0.8143 (16)	0.2278 (6)	0.067*
C9	0.6067 (3)	0.76024 (14)	0.08901 (4)	0.0552 (4)
H9	0.6619	0.7143	0.0631	0.066*
C10	0.7244 (3)	0.73365 (14)	0.13057 (5)	0.0536 (4)
H10	0.8598	0.6702	0.1329	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0688 (7)	0.0527 (6)	0.0378 (5)	0.0162 (5)	−0.0078 (4)	−0.0042 (4)
C1	0.0538 (8)	0.0470 (8)	0.0505 (8)	0.0073 (6)	0.0032 (6)	−0.0004 (6)
C2	0.0455 (7)	0.0381 (6)	0.0349 (6)	−0.0030 (5)	−0.0011 (5)	0.0016 (5)
C3	0.0491 (8)	0.0459 (7)	0.0413 (7)	0.0003 (6)	−0.0055 (5)	0.0057 (6)
C4	0.0534 (8)	0.0541 (8)	0.0349 (7)	−0.0139 (7)	−0.0006 (5)	0.0057 (5)
C5	0.0676 (10)	0.0772 (10)	0.0368 (7)	−0.0170 (8)	−0.0082 (6)	0.0073 (6)
C6	0.0660 (10)	0.0653 (9)	0.0348 (6)	−0.0031 (8)	−0.0081 (6)	0.0054 (6)
C7	0.0456 (7)	0.0415 (7)	0.0386 (6)	−0.0018 (5)	−0.0004 (5)	0.0071 (5)
O8	0.0644 (7)	0.0597 (6)	0.0426 (6)	0.0163 (5)	−0.0077 (5)	0.0057 (4)
C9	0.0643 (9)	0.0621 (9)	0.0393 (7)	−0.0016 (7)	0.0112 (6)	−0.0037 (6)
C10	0.0564 (8)	0.0544 (8)	0.0500 (8)	0.0109 (7)	0.0084 (6)	0.0038 (6)

Geometric parameters (Å, º) top

O1—C1	1.4228 (16)	C5—H5A	0.9900
O1—C2	1.3732 (15)	C5—H5B	0.9900
C1—H1A	0.9800	C5—C6	1.500 (2)
C1—H1B	0.9800	C6—C6ⁱ	1.304 (3)
C1—H1C	0.9800	C6—H6	0.9500
C2—C3	1.3834 (17)	C7—O8	1.3720 (15)
C2—C7	1.3921 (18)	C7—C10	1.3751 (19)
C3—H3	0.9500	O8—H8	0.777 (17)
C3—C4	1.3938 (18)	C9—H9	0.9500
C4—C5	1.5183 (17)	C9—C10	1.386 (2)
C4—C9	1.380 (2)	C10—H10	0.9500

C2—O1—C1	117.26 (10)	H5A—C5—H5B	107.9
O1—C1—H1A	109.5	C6—C5—C4	112.18 (12)
O1—C1—H1B	109.5	C6—C5—H5A	109.2
O1—C1—H1C	109.5	C6—C5—H5B	109.2
H1A—C1—H1B	109.5	C5—C6—H6	116.9
H1A—C1—H1C	109.5	C6ⁱ—C6—C5	126.11 (19)
H1B—C1—H1C	109.5	C6ⁱ—C6—H6	116.9
O1—C2—C3	125.76 (12)	O8—C7—C2	120.87 (11)
O1—C2—C7	114.17 (10)	O8—C7—C10	119.65 (12)
C3—C2—C7	120.07 (11)	C10—C7—C2	119.46 (11)
C2—C3—H3	119.7	C7—O8—H8	108.7 (13)
C2—C3—C4	120.59 (13)	C4—C9—H9	119.5
C4—C3—H3	119.7	C4—C9—C10	121.05 (12)
C3—C4—C5	120.21 (13)	C10—C9—H9	119.5
C9—C4—C3	118.58 (12)	C7—C10—C9	120.23 (13)
C9—C4—C5	121.19 (13)	C7—C10—H10	119.9
C4—C5—H5A	109.2	C9—C10—H10	119.9
C4—C5—H5B	109.2

O1—C2—C3—C4	−178.58 (12)	C3—C2—C7—C10	−1.74 (19)
O1—C2—C7—O8	−1.02 (18)	C3—C4—C5—C6	80.50 (17)
O1—C2—C7—C10	177.67 (12)	C3—C4—C9—C10	−1.4 (2)
C1—O1—C2—C3	−6.20 (19)	C4—C5—C6—C6ⁱ	116.9 (2)
C1—O1—C2—C7	174.44 (11)	C4—C9—C10—C7	0.4 (2)
C2—C3—C4—C5	−177.32 (12)	C5—C4—C9—C10	176.73 (13)
C2—C3—C4—C9	0.8 (2)	C7—C2—C3—C4	0.75 (19)
C2—C7—C10—C9	1.2 (2)	O8—C7—C10—C9	179.89 (13)
C3—C2—C7—O8	179.57 (12)	C9—C4—C5—C6	−97.55 (17)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O1ⁱⁱ	0.78 (2)	2.57 (2)	3.1784 (13)	136 (1)

Symmetry code: (ii) x+1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O1ⁱ	0.778 (17)	2.571 (17)	3.1784 (13)	136.2 (14)

Symmetry code: (i) x+1/2, y, −z+1/2.

Acknowledgements

We are grateful to the National Science Foundation MRI Program (CHE-0951711), the Grote Chemistry Fund at the University of Tennessee at Chattanooga, and to Materia Inc. of Pasadena, CA, USA, for their generous support of our work.

References

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Page o500

doi:10.1107/S2056989015011585

Open

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