7-(Biphenyl-4-yl)-6-hy­droxy­indan-1-one

McCoy, R.N.; Robertson, K.N.; Ylijoki, K.E.O.

doi:10.1107/S2414314619009519

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 7| July 2019| x190951

https://doi.org/10.1107/S2414314619009519

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access

7-(Biphenyl-4-yl)-6-hydroxyindan-1-one

Ryan N. McCoy,^a Katherine N. Robertson ^a and Kai E. O. Ylijoki ^a ^*

^aDepartment of Chemistry, Saint Mary's University, Halifax, NS, Canada
^*Correspondence e-mail: kai.ylijoki@smu.ca

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 7 June 2019; accepted 2 July 2019; online 16 July 2019)

The title compound, C₂₁H₁₆O₂, was isolated from the reaction of 1-(2-methoxyethoxy)-1-vinylcyclopropane, 4-ethynylbiphenyl, and CO in a [5 + 1 + 2 + 1] cycloaddition reaction catalysed by [Rh(CO)₂Cl]₂. The crystals precipitated directly from the crude reaction mixture. A hydrogen-bonding framework between the hydroxy and carbonyl groups of a symmetry-related neighbour connects the molecules into chains running parallel to the crystallographic c axis. A minor non-merohedral twin component was included in the refinement.

Keywords: crystal structure; indanone; biphenyl.

CCDC reference: 1937942

Structure description

The molecular structure of the title compound is shown in Fig. 1. The carbonyl group of the five-membered ring lies out of the indanone ring plane (defined by C1–C9), with a distance of 0.486 (5) Å between O2 and the least-squares plane, while the hydroxyl oxygen essentially lies in the plane [0.078 (5) Å between O1 and the least-squares plane]. The dihedral angle between the indanone ring plane and the plane of the aromatic ring directly bonded to C9 (C10–C15) is 49.6 (1)°, and that within the biphenyl group is smaller at 36.2 (2)°.

Figure 1
Molecular structure of the title compound showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, hydrogen bonds are observed between the OH donor and the carbonyl acceptor of a symmetry-related molecule, creating chains (Figs. 2 and 3; Table 1). The metrics for this intermolecular bond are similar to those in the structurally related compound 6-hydroxy-7-phenyl-1-indanone (refcode YANPIN in the CSD, Groom et al., 2016 ; Wender et al., 2005 ), which crystallizes in the monoclinic space group P2₁/c with unit-cell dimensions a = 12.061 (1), b = 15.232 (1), c = 12.918 Å and β = 102.32°, with two molecules in the asymmetric unit. When compared to the title compound, the carbonyl is more in plane with the indanone ring framework (0.230 and 0.161 Å deviations from the plane for the carbonyl O atoms of the two independent molecules), the hydroxyl O atoms are again coplanar with the indanone (0.096 and 0.004 Å deviations), and the dihedral angle between the indanone and phenyl planes is larger (61.4 and 60.8°; Wender et al., 2005). The hydrogen-bonding framework is similar in both crystal structures.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.89 (2)	1.86 (2)	2.734 (4)	168 (5)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Diagram showing the intermolecular hydrogen-bonding pattern. Ellipsoids are drawn at the 50% probability level. Hydrogen bonds are drawn as dashed black lines.

Figure 3
Packing diagram of the title compound viewed along the a axis. Ellipsoids are drawn at the 50% probability level.

Synthesis and crystallization

The title compound was prepared through a modification of the published procedure (Wender et al., 2005). An amount of 1-(2-methoxyethoxy)-1-vinylcyclopropane (17.1 mg, 0.1203 mmol) was dissolved in toluene-d₈ (300 µL). The catalyst [Rh(CO)₂Cl]₂ (0.6 mg, 0.0015 mmol) was added, followed by 4-ethynylbiphenyl (10.7 mg, 0.0600 mmol) in toluene-d₈ (300 µL). The solution was placed in an NMR tube and capped with a septum. The tube was removed from the glovebox and, via a needle, the headspace was purged with CO gas. The tube was heated at 60°C for 40 h in an oil bath. As the reaction proceeded, the product precipitated from solution as tiny pale yellow–brown crystals. The NMR spectroscopic data were in agreement with those previously reported.

Refinement

Crystal data, data collection, and structure refinement details are summarized in Table 2. One reflection ( $[\overline8]$ 1 3) showed poor agreement in the final refinement and was omitted in the last cycles. The routine TwinRotMax implemented in PLATON (Spek, 2009 ) indicated that there was a minor twin component present in the crystal. The twin law, [ $[\overline{1}]$ 0 0, 0 $[\overline{1}]$ 0, 0.668 0 1], was added to the refinement and the batch scale factor refined to 0.0034 (7). Inclusion of the twin law did improve the statistics of the refinement slightly.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₆O₂
M_r	300.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	125
a, b, c (Å)	9.384 (3), 11.032 (4), 14.827 (5)
β (°)	102.609 (4)
V (Å³)	1498.0 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.508, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	14915, 2745, 1711
R_int	0.117
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.233, 1.08
No. of reflections	2745
No. of parameters	212
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.31
Computer programs: APEX2 and SAINT (Bruker, 2008 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1937942

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619009519/bh4047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619009519/bh4047Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619009519/bh4047Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

7-(Biphenyl-4-yl)-6-hydroxyindan-1-one top

Crystal data top

C₂₁H₁₆O₂	F(000) = 632
M_r = 300.34	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.384 (3) Å	Cell parameters from 2589 reflections
b = 11.032 (4) Å	θ = 2.2–24.7°
c = 14.827 (5) Å	µ = 0.09 mm⁻¹
β = 102.609 (4)°	T = 125 K
V = 1498.0 (9) Å³	Plate, yellow
Z = 4	0.23 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	2745 independent reflections
Radiation source: sealed tube	1711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.117
φ and ω scans	θ_max = 25.4°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.508, T_max = 0.745	k = −13→13
14915 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.079	Hydrogen site location: mixed
wR(F²) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.1129P)² + 1.384P] where P = (F_o² + 2F_c²)/3
2745 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³
0 constraints

Special details top

Refinement. Refined as a 2-component twin. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms bonded to carbon were included at geometrically idealized positions and were not refined. The isotropic thermal parameters of the hydrogen atoms were fixed at 1.2U_eq of the parent carbon atom and 1.5U_eq for the hydrogen bonded to oxygen. A bond length restraint was applied to the hydroxyl group, O—H = 0.85 (2) Å, to keep its geometry reasonable.

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

	x	y	z	U_iso*/U_eq
O1	0.1692 (3)	0.6107 (2)	0.01317 (18)	0.0288 (7)
H1	0.172 (5)	0.617 (4)	−0.0462 (15)	0.043*
O2	0.2090 (3)	0.8497 (3)	0.33830 (19)	0.0334 (8)
C1	0.1781 (4)	0.7254 (3)	0.0493 (3)	0.0232 (9)
C2	0.1621 (5)	0.8252 (3)	−0.0101 (3)	0.0261 (10)
H2	0.142119	0.812662	−0.075041	0.031*
C3	0.1749 (5)	0.9418 (4)	0.0245 (3)	0.0282 (10)
H3	0.163642	1.009427	−0.016059	0.034*
C4	0.2041 (4)	0.9583 (3)	0.1182 (3)	0.0240 (9)
C5	0.2194 (5)	1.0771 (4)	0.1702 (3)	0.0334 (11)
H5A	0.125839	1.122054	0.157794	0.040*
H5B	0.295471	1.128578	0.152723	0.040*
C6	0.2631 (6)	1.0398 (4)	0.2708 (3)	0.0355 (11)
H6A	0.205684	1.084921	0.308427	0.043*
H6B	0.368244	1.055469	0.295778	0.043*
C7	0.2303 (5)	0.9043 (4)	0.2713 (3)	0.0269 (10)
C8	0.2171 (4)	0.8599 (3)	0.1774 (3)	0.0221 (9)
C9	0.2065 (4)	0.7385 (3)	0.1440 (3)	0.0211 (9)
C10	0.2317 (4)	0.6321 (3)	0.2074 (3)	0.0229 (9)
C11	0.1350 (5)	0.5348 (3)	0.1952 (3)	0.0258 (9)
H11	0.051340	0.535998	0.145762	0.031*
C12	0.1593 (5)	0.4362 (3)	0.2543 (3)	0.0272 (10)
H12	0.091898	0.370758	0.244835	0.033*
C13	0.2803 (4)	0.4312 (3)	0.3270 (3)	0.0232 (9)
C14	0.3793 (5)	0.5282 (3)	0.3376 (3)	0.0269 (10)
H14	0.464594	0.526389	0.385879	0.032*
C15	0.3534 (5)	0.6263 (3)	0.2783 (3)	0.0262 (10)
H15	0.421510	0.691227	0.286679	0.031*
C16	0.3046 (4)	0.3278 (3)	0.3935 (3)	0.0233 (9)
C17	0.4434 (5)	0.2874 (4)	0.4329 (3)	0.0286 (10)
H17	0.525244	0.323702	0.415471	0.034*
C18	0.4652 (5)	0.1946 (4)	0.4975 (3)	0.0347 (11)
H18	0.561178	0.166813	0.523397	0.042*
C19	0.3472 (5)	0.1429 (4)	0.5239 (3)	0.0308 (10)
H19	0.362012	0.080224	0.568952	0.037*
C20	0.2083 (5)	0.1815 (3)	0.4855 (3)	0.0271 (10)
H20	0.127052	0.144838	0.503248	0.033*
C21	0.1865 (5)	0.2742 (3)	0.4205 (3)	0.0249 (9)
H21	0.090167	0.301150	0.394404	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0458 (19)	0.0126 (14)	0.0283 (16)	−0.0004 (12)	0.0085 (14)	−0.0015 (12)
O2	0.051 (2)	0.0207 (16)	0.0288 (17)	0.0034 (14)	0.0101 (14)	0.0019 (13)
C1	0.025 (2)	0.013 (2)	0.032 (2)	−0.0017 (16)	0.0078 (18)	−0.0009 (17)
C2	0.032 (2)	0.018 (2)	0.028 (2)	0.0003 (17)	0.0057 (18)	0.0013 (17)
C3	0.036 (3)	0.014 (2)	0.036 (3)	0.0034 (17)	0.011 (2)	0.0052 (18)
C4	0.028 (2)	0.0111 (19)	0.036 (2)	0.0009 (16)	0.0123 (18)	0.0054 (17)
C5	0.049 (3)	0.012 (2)	0.039 (3)	0.0012 (19)	0.010 (2)	−0.0014 (18)
C6	0.056 (3)	0.014 (2)	0.039 (3)	−0.0050 (19)	0.016 (2)	−0.0049 (18)
C7	0.028 (2)	0.018 (2)	0.033 (2)	0.0050 (17)	0.0031 (18)	0.0036 (18)
C8	0.028 (2)	0.0136 (19)	0.025 (2)	0.0016 (16)	0.0064 (17)	0.0025 (16)
C9	0.022 (2)	0.0119 (19)	0.029 (2)	0.0003 (15)	0.0060 (17)	0.0005 (16)
C10	0.031 (2)	0.0104 (19)	0.027 (2)	−0.0003 (16)	0.0073 (18)	−0.0016 (16)
C11	0.029 (2)	0.019 (2)	0.029 (2)	−0.0022 (17)	0.0058 (18)	0.0032 (17)
C12	0.033 (2)	0.014 (2)	0.034 (2)	−0.0028 (17)	0.0072 (19)	0.0009 (18)
C13	0.029 (2)	0.0122 (19)	0.029 (2)	0.0008 (17)	0.0084 (18)	0.0007 (16)
C14	0.029 (2)	0.016 (2)	0.034 (2)	0.0016 (17)	0.0028 (18)	0.0014 (17)
C15	0.029 (2)	0.014 (2)	0.035 (2)	−0.0010 (17)	0.0074 (19)	0.0029 (17)
C16	0.030 (2)	0.0128 (19)	0.027 (2)	−0.0001 (17)	0.0055 (18)	−0.0013 (16)
C17	0.028 (2)	0.015 (2)	0.042 (3)	0.0015 (17)	0.007 (2)	0.0038 (18)
C18	0.035 (3)	0.018 (2)	0.047 (3)	0.0020 (19)	0.002 (2)	0.009 (2)
C19	0.043 (3)	0.014 (2)	0.034 (2)	−0.0013 (19)	0.006 (2)	0.0047 (18)
C20	0.036 (3)	0.016 (2)	0.030 (2)	−0.0026 (18)	0.0095 (19)	0.0010 (17)
C21	0.030 (2)	0.013 (2)	0.031 (2)	0.0017 (17)	0.0061 (18)	0.0006 (17)

Geometric parameters (Å, º) top

O1—C1	1.369 (5)	C10—C11	1.393 (5)
O1—H1	0.887 (19)	C11—C12	1.384 (5)
O2—C7	1.214 (5)	C11—H11	0.9500
C1—C9	1.380 (6)	C12—C13	1.386 (5)
C1—C2	1.397 (5)	C12—H12	0.9500
C2—C3	1.380 (6)	C13—C14	1.403 (6)
C2—H2	0.9500	C13—C16	1.492 (5)
C3—C4	1.369 (5)	C14—C15	1.383 (5)
C3—H3	0.9500	C14—H14	0.9500
C4—C8	1.384 (5)	C15—H15	0.9500
C4—C5	1.512 (5)	C16—C17	1.381 (6)
C5—C6	1.515 (6)	C16—C21	1.391 (6)
C5—H5A	0.9900	C17—C18	1.386 (6)
C5—H5B	0.9900	C17—H17	0.9500
C6—C7	1.527 (6)	C18—C19	1.377 (6)
C6—H6A	0.9900	C18—H18	0.9500
C6—H6B	0.9900	C19—C20	1.371 (6)
C7—C8	1.456 (6)	C19—H19	0.9500
C8—C9	1.423 (5)	C20—C21	1.389 (6)
C9—C10	1.490 (5)	C20—H20	0.9500
C10—C15	1.374 (5)	C21—H21	0.9500

C1—O1—H1	108 (3)	C15—C10—C9	120.7 (3)
O1—C1—C9	118.5 (3)	C11—C10—C9	121.1 (4)
O1—C1—C2	119.5 (3)	C12—C11—C10	120.7 (4)
C9—C1—C2	122.0 (4)	C12—C11—H11	119.6
C3—C2—C1	120.7 (4)	C10—C11—H11	119.6
C3—C2—H2	119.6	C11—C12—C13	121.2 (4)
C1—C2—H2	119.6	C11—C12—H12	119.4
C4—C3—C2	118.9 (4)	C13—C12—H12	119.4
C4—C3—H3	120.5	C12—C13—C14	117.9 (4)
C2—C3—H3	120.5	C12—C13—C16	121.7 (3)
C3—C4—C8	120.6 (4)	C14—C13—C16	120.5 (4)
C3—C4—C5	127.5 (4)	C15—C14—C13	120.4 (4)
C8—C4—C5	111.8 (3)	C15—C14—H14	119.8
C4—C5—C6	104.0 (3)	C13—C14—H14	119.8
C4—C5—H5A	111.0	C10—C15—C14	121.6 (4)
C6—C5—H5A	111.0	C10—C15—H15	119.2
C4—C5—H5B	111.0	C14—C15—H15	119.2
C6—C5—H5B	111.0	C17—C16—C21	118.6 (4)
H5A—C5—H5B	109.0	C17—C16—C13	121.3 (4)
C5—C6—C7	105.0 (3)	C21—C16—C13	120.0 (4)
C5—C6—H6A	110.7	C16—C17—C18	120.9 (4)
C7—C6—H6A	110.7	C16—C17—H17	119.5
C5—C6—H6B	110.7	C18—C17—H17	119.5
C7—C6—H6B	110.7	C19—C18—C17	119.8 (4)
H6A—C6—H6B	108.8	C19—C18—H18	120.1
O2—C7—C8	128.4 (4)	C17—C18—H18	120.1
O2—C7—C6	123.9 (4)	C20—C19—C18	120.2 (4)
C8—C7—C6	107.4 (3)	C20—C19—H19	119.9
C4—C8—C9	121.9 (4)	C18—C19—H19	119.9
C4—C8—C7	108.7 (3)	C19—C20—C21	120.0 (4)
C9—C8—C7	129.3 (3)	C19—C20—H20	120.0
C1—C9—C8	115.8 (3)	C21—C20—H20	120.0
C1—C9—C10	121.9 (3)	C20—C21—C16	120.5 (4)
C8—C9—C10	122.2 (3)	C20—C21—H21	119.8
C15—C10—C11	118.2 (4)	C16—C21—H21	119.8

O1—C1—C2—C3	−178.1 (4)	C1—C9—C10—C15	127.8 (4)
C9—C1—C2—C3	0.3 (7)	C8—C9—C10—C15	−49.1 (6)
C1—C2—C3—C4	0.2 (6)	C1—C9—C10—C11	−50.5 (6)
C2—C3—C4—C8	−1.5 (6)	C8—C9—C10—C11	132.6 (4)
C2—C3—C4—C5	−178.7 (4)	C15—C10—C11—C12	1.5 (6)
C3—C4—C5—C6	−175.6 (4)	C9—C10—C11—C12	179.9 (4)
C8—C4—C5—C6	7.0 (5)	C10—C11—C12—C13	−0.1 (6)
C4—C5—C6—C7	−14.8 (5)	C11—C12—C13—C14	−1.4 (6)
C5—C6—C7—O2	−157.0 (4)	C11—C12—C13—C16	177.5 (4)
C5—C6—C7—C8	18.0 (5)	C12—C13—C14—C15	1.6 (6)
C3—C4—C8—C9	2.4 (6)	C16—C13—C14—C15	−177.3 (4)
C5—C4—C8—C9	−180.0 (4)	C11—C10—C15—C14	−1.3 (6)
C3—C4—C8—C7	−173.2 (4)	C9—C10—C15—C14	−179.7 (4)
C5—C4—C8—C7	4.4 (5)	C13—C14—C15—C10	−0.2 (6)
O2—C7—C8—C4	160.6 (4)	C12—C13—C16—C17	146.5 (4)
C6—C7—C8—C4	−14.0 (5)	C14—C13—C16—C17	−34.6 (6)
O2—C7—C8—C9	−14.6 (7)	C12—C13—C16—C21	−36.8 (6)
C6—C7—C8—C9	170.8 (4)	C14—C13—C16—C21	142.1 (4)
O1—C1—C9—C8	178.9 (3)	C21—C16—C17—C18	0.5 (6)
C2—C1—C9—C8	0.5 (6)	C13—C16—C17—C18	177.3 (4)
O1—C1—C9—C10	1.8 (6)	C16—C17—C18—C19	−0.9 (7)
C2—C1—C9—C10	−176.6 (4)	C17—C18—C19—C20	1.1 (7)
C4—C8—C9—C1	−1.9 (6)	C18—C19—C20—C21	−0.9 (6)
C7—C8—C9—C1	172.8 (4)	C19—C20—C21—C16	0.5 (6)
C4—C8—C9—C10	175.2 (4)	C17—C16—C21—C20	−0.3 (6)
C7—C8—C9—C10	−10.1 (7)	C13—C16—C21—C20	−177.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.89 (2)	1.86 (2)	2.734 (4)	168 (5)

Symmetry code: (i) x, −y+3/2, z−1/2.

Funding information

Financial support from the Canada Foundation for Innovation (CFI), the Faculties of Science and Graduate Studies and Research of Saint Mary's University, and the Natural Sciences and Engineering Research Council of Canada (NSERC USRA to RNM) is gratefully acknowledged.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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